Nitish Upadhyaya leads the ideas and investment (i2) team within Allen & Overy’s Legal Technology Group, prototyping and delivering solutions which tackle pain points raised by A&O staff and clients.

A former litigator, Nitish is fascinated by people and the processes by which we can surface, refine, communicate and action ideas effectively. It’s little surprise that Nitish is also passionate about behavioural science and user centric design to make better decisions, challenge assumptions, structure thinking and create great solutions to novel problems.

In this interview we also touch on the critical importance of change management, fostering an open culture and embracing the adjacent possible to gradually push the forward frontier of innovation within large organisations rather than chase elusive moonshots.

Nitish is a great example of someone who has found their groove at the intersection of several interests and experiences, spanning law, technology, behavioural science and design — all of which are increasingly critical to the future of law.

Outside of work, Nitish is also a prolific explorer (his most recent trip was to Ethiopia) and is an impressive travel photographer.

So how does a litigator segue into innovation? Let’s find out!

Nitish, how did your career begin?

After university I completed my training contract at A&O. I had a chance to do four quite different seats in project finance, securitisation, financial and regulatory litigation and derivatives.

My final seat was in Hong Kong — a chance to explore a new part of the world but also to get to grips with what an international law firm is really all about. You can do transactions and cases with people from all around the world from London, but there’s no substitute for experiencing different cultures (and appreciating the impact of time zones).

I’m a big traveller. Spending lots of time in Hong Kong also gave me a fantastic base to go and explore Southeast Asia and Japan. In many ways, it was the genesis for me in terms of also wanting to travel more and really taking advantage of that whenever possible.

I’ve always tried to intersperse my career with lots of travel. Before I joined A&O I took six months off to travel South America and work in Tanzania, and every couple of years I’ve managed to complete a big trip. It’s kept me sane and has also fed my other passions — travel photography (see here for some of Nitish’s amazing shots) and food!

At the end of my training contract I qualified into litigation. I did so at an interesting time. The post-Lehman Brothers cases were still rumbling on regarding misselling of financial products, including complex derivatives, and also around that same time was when international forex trading was subject to big regulatory investigations — these were massively complex, involving multiple jurisdictions and lots of different regulators. This made for some very topical and complex work to start my qualified career.

Whilst in litigation I had the chance to work in New York and DC, which meant extensive time facing US regulators along with plenty of time in the UK Commercial Court. The work covered everything from ridiculous freezing injunctions at about two minutes notice to scoping and presenting remediation initiatives to regulators with clients.

What is a freezing injunction?

A freezing injunction is a court order that prevents a party from disposing of or dealing with its assets. The idea is to prevent a defendant — whether innocent or guilty — to an action from dissipating their assets from beyond the jurisdiction of a court so as to frustrate a potential judgment. A freezing injunction is therefore an essential tool for those looking to protect assets to ensure those assets are available to satisfy a court order.

All in all it was pretty varied!

However, as much as I loved working with the litigation team, I began to think it wasn’t what I wanted to do long-term. I spoke to my sponsor partners at A&O and organised a career break, taking 9 months off. The openness with which I was able to have this conversation endeared me to the firm even more.

In that time I went travelling again and also worked with my charity, the Mondo Foundation to scope and launch an employability project in Nepal, working alongside the British Embassy in Nepal, British Council, the DiFID and social entrepreneurs.

I’ve been working with Mondo Foundation for well over ten years, including before I joined A&O. My work with the Mondo Foundation is something I’ve carried with me throughout my time at A&O, and the firm has always been incredibly supportive of my involvement with the project, so it was great to spend some focused time with them whilst on my career break. I recently stepped down as trustee to help refresh the Board but still maintain strong links with the Foundation.

What is Mondo Foundation?

Mondo Foundation is a UK based charity that works to provide sustainable support for education and livelihoods in developing countries. Mondo Foundation was established in 2004 and works primarily in NE India, Nepal and Tanzania. Mondo Foundation works to empower local communities, working on projects that are bottom-up in nature and therefore predicated on long-term sustainability.

Did your career break change how you viewed your career, and what you wanted to do next?

Yes it did. I came back and realised by then that I didn’t want to return to litigation. I’d started to look at the world in a different way. I’d begun thinking about using my experiences as a practising lawyer and the ways in which to rethink how myself and my colleagues worked. That led me into taking on an innovation role at A&O upon my return. In essence I’d realised that I was more and more interested in the business of law and transforming that, than necessarily the practising element alone.

And that brings us up to date — I now lead the innovation team at A&O, known as i2.

Can you tell us a little about i2?

Certainly. My role at i2 focuses on prototyping and delivering solutions which tackle pain points raised by A&O staff and clients. We take crowdsourced ideas from concept to prototype and onwards to core investment. We also help stakeholders think differently about challenges, be it getting a new view on how to run a process or developing their longer term strategy.

My team includes an innovation manager, business analysts, a UX / UI specialist and a bench of developers, and we utilise design thinking methodology to build out concepts, prove value and deliver solutions. My core role is encouraging people to think about, and do, things differently against the background of facilitating genuine, sustainable behaviour change.

In action that means a broad range of activities. One day I might be focused on crafting and leading user-centred design workshops with participants across the globe to surface problems and challenge assumptions in advance of process or product development. On another day, I’ll be advising on the adoption of new technology and leading change management exercises using a behavioural lens, including in the creation and testing of messaging, designing for incremental change, and stakeholder management.

These activities tend to generate a lot of enthusiasm and engagement. For me my role is about chasing the fun — it lets me express my creativity, help others do the same, and at the same time make a tangible difference by pulling together lots of different learning from across the different domains and the many diverse individuals at A&O and on the client side.

Touching on that point, what were the initial things that drew you toward an innovation role?

I’ve always been really interested in human behavior. The more time I spent crunching through bog standard processes with colleagues and clients, the more it became apparent to me that these processes weren’t primed for efficiency in the sense of being aligned to how and why people behave as they do. We weren’t learning lessons and improving things.

Part of that comes with the territory of modern legal practice — everyone is always busy and working hard and doesn’t naturally have the headspace to zoom out and assess whether things can be improved, or should be improved, and if so, how and why.

As a practising lawyer, you’re immersed in law, trying to build your career, engaging with clients, keeping up with your legal knowledge and so on. There’s only so much your head can handle, and very little free time to spend on other activities like process improvement or product development even if, ironically, doing so would improve your work / life balance and career progression.

I needed to get outside of that, to create the space you need for creativity and thinking outside the box about processes and systems, and to engage with the right people, to learn from them and to work with them.

As soon as you create that space, you gain this magical perspective on how things work. You are building links with other people in the industry or outside of the industry. It’s those outside viewpoints I think that are really important, and keep me going, because they demonstrate that just because something is done this way, and has been for some time, that it isn’t the only way and can in all likelihood be improved, often with learnings from other disciplines.

Are there particular aspects of organisational change that your innovation role and team prioritises?

There’s this wonderful theory of the adjacent possible, where you’ve got crazy ideas at the periphery of what’s generally possible based on the status quo, and between that and the status quo there is a breadth of more immediately doable things. Those things, if tackled, form stepping stones to the massively transformational projects at the periphery. It’s those in between things that are the adjacent possible ideas. These ideas usually need a push, and together can add up to something significant that nudges the organisation toward truly transformational change.

The key thing is that you can’t easily leapfrog the adjacent possible. It’s very hard to do, i.e. to skip several steps. People do, of course, and you get an almighty new invention, but maybe less so in professional services.

In some ways it’s like learning a new skill — you can’t go from paint by numbers to a masterpiece, you need to level up through intermediate skill acquisition. There are few shortcuts!

In the initial stages of my new role, this is what I focused on — tackling the adjacent possible ideas.

It works well because you are starting from ideas that people are already aware of, and to different degrees understand and to which there is already institutional openness.

As such, and importantly, these ideas aren’t so radical as to seem impossible or remote in their conception or the steps required to action them. The only reason the adjacent possible ideas haven’t yet been tackled is usually bandwidth — individuals and teams not having the time to think about the ideas and execute upon them.

So the real joy of my job is being a specialist at spotting these adjacent possible ideas, facilitating their solution among our teams and clients, and thereby consistently pushing the frontier forward into successively more innovative ideas and opportunities further out and nearer the periphery of what’s possible.

At A&O I’m lucky to have a sort of significant technology team behind me to help implement these ideas. Complementing this further is A&O Fuse, which is an amazing space, giving lawyers and start up teams opportunity for spontaneous and relaxed interactions.

You can walk around Fuse, speak to different start-ups or individuals working there and simply ask them “Hey, what do you think about this idea. Can we have a quick coffee to discuss?” or “How do you think this works out? Is this a silly idea or is there something in it?” or “Can we work together on solving this or that? What do you think?”.

Fuse is a good example of how creating the right environment can foster that open collaboration and make things less formal. In the more traditional set-up these types of interactions would require making an appointment and visiting someone at their office etc, all of which add unhelpful friction to these more creative interactions. I’ve certainly missed this casual interaction during the pandemic.

In summary, what drew me to the role is the opportunity to interrogate things from a different perspective, the chance to harness and apply my creativity and to explore things from a human centred perspective. I’ll be the first to admit I’m not a techie. I have a vague and increasing understanding of coding and software engineering and the design principles that surround it, but my focus is on the before and after, understanding how people interact with problems, processes, each other, solutions and ideas and turning those observations into actionable insights to create, improve or update the products and services we are building at A&O for colleagues and clients. Knowing what people say they do and understanding what they actually do are often very different things. A lot of my job is understanding that disconnect and helping individuals and teams solve their actual versus assumed needs.

The i2 team sounds like a great mix of specialisms like the Avengers, where everyone brings their own separate but complementary skills and experiences in solution of multi-disciplinary problems that can’t be solved alone. Do you think this is the preferable set-up vs trying to cram multiple skills and functions into a handful of innovation Jacks or Janes of all trades?

To my mind, the way we have i2 set up is very fortunate, and the better approach.

As any individual, if you’re wearing too many hats too often, you’re context switching a lot, and probably far too much. Context switching is cognitively costly. These switches interrupt thinking and productivity. It doesn’t make sense when viewed from that perspective. It’s as simple as that.

The other thing to say is that if you can afford to create specialist roles filled by specialists, for example, a UX / UI designer, that individual will be keeping up to date with trends in the market, and bring a wealth of experience with them into the role and into the wider team and by extension, the organisation.

When an experienced UX / UI expert enters a room, they bring credibility and knowledge about the thing that they do, much like a developer does when the conversation pivots to software engineering aspects of a project. These perspectives are important and need to be enabled, encouraged and respected.

A good balance is what we’ve built, a team combining legal domain knowledge with outside expertise, that together means the whole is greater than the sum of its parts.

And that makes a massive difference.

No doubt there are a minority of superhuman individuals who thrive on juggling four or maybe five roles. Start-up founders are perhaps that type, at least initially, but they usually and often quite quickly, need to relinquish control, delegate and build a diverse team of complementary talents and experiences.

And so while a lot of law firm innovation functions may start off with one or two people who are doing a lot of things, and very quickly need to prove that they make sense as a function, there soon comes a point where it makes more sense to begin creating specialist roles and a multidisciplinary team.

Your organization is poorer for not having diversity of specialisms because of the cognitive diversity such teams create, especially where your team is leveraging experiences from different industries, not just law.

Even with larger and more established teams, the missing component is usually someone with the UX / UI and general design skills. Often the first specialist hires at legal organisations are the developers or analysts, and sometimes teams stop there. Whilst those personas are part of the solution, it still leaves a gap for good design, which those individuals may not necessarily possess, or desire to learn.

Why do you think it is that important to have a strong design capability in the team such as yours?

When developing any product or service, you need to find common ground among users of different types — the unmet need that they share, and the general execution on that problem that best solves that need for the most people in the best possible way.

What you do not want to do is solve that need for a singular person.

Often when I work with lawyers they have a very specific view of what a solution needs to be, look like and function in a certain way… yet in reality it might make no sense to 99% of similar users. The thing that they articulate may very well be only their view of the world.

That view is important, and should be listened to. However, it is only one view. You need to gather other views and test these against each other to understand where the common ground lies, which will be a starting point for development of a common solution that scales.

Having design skills in the team can help tease out the unmet needs of a cohort of users and balance those against individual requirements where appropriate.

Compared to your earlier career as a litigator, was there anything you found particularly transferable to your current role, and equally anything you’ve had to unlearn from that role in order to succeed in your current role?

I think the reason I went into litigation instead of a transactional team was because I really enjoy pulling things apart rather than putting things together, which sounds strange given my current role!

It’s given me that critical eye in terms of what’s going to go wrong or could go wrong, and ability to question things in a structured manner.

That is useful when trying to assess which of several competing ideas are better or worse than one another, and kill an idea if it isn’t or becomes unworkable.

Just because somebody is shouting really loudly about an idea, their idea, doesn’t mean it’s a good one. I find my litigation background useful to assess the arguments for and against an idea, and to challenge — in a sensitive way — other people’s ideas.

It’s not about writing off ideas, but allowing ideas to be tested and thereby letting the best ideas win, rather than politics or personalities.

Once you’ve got the best ideas tested and prioritised, then you’ve got plenty of people who love doing the building and putting things together and that sort of thing.

That interrogative ability is also useful to keep things in check.

Innovation roles and activities can easily get a little carried away — and actually what you really need to do is to calm down and say:

“Let’s just take a step back for a moment to think about this. Is this the right course of action? Are their other options? Can we structure the thinking? Can we go to the root cause? Can we test these options and remove some of the subjectivity? Let me spend a couple of days working with you in your day-to-day, and let’s see how that works and whether or not those observations change what we wish to pull together, and what you need etc.”

I think this really comes from my litigation background. You get used to reading people, and assessing if a witness is fudging a point or if their story is muddled or their thinking unclear. A lot of my current role is to test other people’s ideas, diplomatically getting individuals to think twice about their idea and to back it up, or be prepared to back it up, with some evidence to understand whether or not the idea is worth pursuing.

It’s not uncommon for someone to have an idea, but not really have thought about its value beyond themselves. Simply asking them how many times a year they encounter the problem, how much of an issue it is, whom else it affects and the relative impact of it not being solved can start to get that person’s gears going, and help them do some of the homework about whether or not this idea is only important to them and no one else, or a macro problem that has significant wider value if solved.

The other side of litigation I enjoyed, and enjoy applying in my current role is writing. I really just love writing.

That energy isn’t necessarily directed towards writing publications and that sort of thing. As a litigator you’re taught to make every sentence count. If you’re trying to persuade someone that your point of view, your conclusions and the arguments that back them are the right ones. To do that, you need to be able to write well. Writing can be an excellent way to focus and hone that message. As a litigator you get good at storytelling, which is a critical communication tool for innovation roles.

Good communication is also crucially important in an innovation role because your job is to translate between technologists and lawyers and other business personas to ensure that each side understands each other in the right way. Getting those communications correct makes a big difference in terms of how people perceive things, how they frame a problem and a solution. It also makes the difference between successful or unsuccessful collaboration.

If there’s anything I’ve had to unlearn, it’s that you don’t need to work crazy hours to accomplish a remarkable amount. A normal work day well organised is more than enough, and significantly better overall.

The legal industry moves at a million miles an hour, and in the long term that can have a real impact on its people and their wellbeing. You need the space to disconnect, reset and return to work revitalised. Simply working all the time and always being on doesn’t allow that space, which is key to more creative disciplines like the one I am in today. It’s probably more a general lawyer mindset I’ve had to unlearn in that regard more than a litigation specific mindset.

But with the right thinking, the right mindset and the right team you can formulate much better ways of working and achieve some pretty striking results within a normal working day.

You have to trust yourself, and be disciplined. For instance, yesterday I had two slots, each two and half hours, where I just switched off my emails and made the space for deep work. Unsurprisingly, the world didn’t end in those two windows! It never does. Overall I got a lot more done, both in terms of quantity and quality of output. This type of discipline is something I’ve learnt to do and it’s been really surprising, in a great way, how much more productive I am within those hours. That said, it’s not always possible as a lawyer, which is another reason I decided to make the career switch, and why I’ve really enjoyed this role. I love being able to make time for deep work that is creative.

You’re also undertaking an MSc in Behavioural Science at the LSE. What excited you about the MSc — is it the general interest in that subject matter you mentioned? What are you hoping to learn from it, and are you looking to apply those learnings to your current work?

I think that the starting point is very much a prevailing interest in people. If you look at the world at the moment, you think about fake news and polarisation, or you think about diversity and inclusion, or you think about the state of politics, a lot of that is human behavior and lots of it stems from entrenched problems.

This makes for an incredibly fertile time to study human behaviour. I want to understand that, and on a personal level, make better decisions.

The fun part for me is the combination of psychology and other disciplines to essentially answer the question of how do we make better decisions? And then ultimately, how do you then apply that to your organization? For example, how do you kick off a project and make sure you’re actually thinking about all the things that could go wrong at the start, and planning for them upfront and navigating any behavioural pitfalls?

Thinking about innovation specifically, having a better understanding of behavioural science aids in change management and adoption of new processes and technologies. You can’t simply send out mass email after mass email highlighting a new technology or process and expect instant and prolific adoption across your organisation. You need to understand behaviours and how to use these to your advantage in order to drive change.

It’s another example of what I was describing earlier — the need in law for legal organisations to learn around their domain, to leverage the best ideas from other domains and bring in outside expertise, whether through individuals, training or both.

For me that adjacent discipline is behavioural science, for others its data science or software engineering etc. The key thing is enriching the business of law with these types of outside expertise and experiences — this is going to be fundamental to the industry’s continuing evolution, and its survival.

The pace of change is fast, and perhaps faster than we realize. I was talking to a client yesterday, who said, “Why has the reliance on and recourse to our intranet diminished? What’s changed?”.

My answer was that in their daily lives, people use Google. People expect the same user experience, same ability to search and locate information — but that’s generally far from intuitive on aging intranet sites. The user interface and experience generally isn’t there for technology used in the professional sphere by lawyers (although that is changing)

If you look at any popular consumer product it will be heavily design driven. Those businesses are thinking about behaviour. They are trying to fit the needs of real users, rather than some random stereotype of whatever an individual thinks a user is or might be. Those businesses have spent countless hours refining user stories and user journeys, testing interfaces and experiences with real users and as a result hitting upon products and services that users love.

A good example are mobile only banking start-ups. They’ve totally rethought the traditional experience, and have done away with many of the clunky processes consumers detested but accepted absent of better alternatives. These newer entrants are leapfrogging incumbents through great design, hiving off customers and business in the process.

However when you use products and services in your professional life, particularly in large organisations, those products and services often remain quite clunky and poorly designed. Businesses that are prioritising design as part of their long term strategy will be the ones that prosper. They are going to be fun places to work, the organisations that hoover up the best talent and not full of dinosaurs.

So in summary, my MSc is driven by a combination of personal interest and practical application. The other part is personal improvement — as I say, how I can make better decisions in my life and help others do the same? That’s a key question I want to answer.

That’s very true regarding the disconnect between consumer and enterprise solutions. In many legal innovation efforts, receptiveness to design principles — and doing them properly — remains quite immature, but where it’s enabled and supported by an open minded and respectful culture it can make such a big difference to the success of those projects.

Likewise, clients are starting to expect that certain services be delivered via experiences more akin to those they experience with other professional advisors, and in their consumer life.

Those experiences are raising the bar for legal, and legal has some catching up to do!

There’s a big opportunity for law firms to get this right, which leads nicely into my next question.

What do you see as the biggest challenges and opportunities for legal innovation, including law firms, in-house teams, and maybe from a vendor perspective as well?

I think the ultimate goal is to instill an innovation mindset in individuals, and create an innovation culture within an organisation.

That is the biggest opportunity, and perhaps the biggest challenge.

If every single individual in an organisation is enabled and encouraged to think about innovation in the way they work, so much so that it’s just another core competency, then you raise the probability that individuals and teams will constantly improve how they work and the value they create for colleagues and consumers of their output.

Now that is obviously easier said than done. At its core it’s about creating a safe space to experiment and take calculated risks, and be instantly supported in doing that.

It’s also about making sure individuals know that their ideas will be actioned (or get feedback on why not). Creating a culture and group expectation that ideas will need to be tested and that many ideas won’t make it all or even part of the way. If you can provide constructive feedback on why not, it breeds further ideas and an openness to exploring new thinking.

That’s the opportunity.

If you succeed, you are harnessing the minds of hundreds or thousands of really bright people in your organisation.

In a law firm many of those people will have exceptionally strong analytical and problem-solving skills they use everyday to solve legal problems for clients. Those same skills can be powerfully applied to solve business of law problems that enable the innovation of the organisation’s processes, products and services. Enabling those individuals to find the time and create the right environment in which to explore and solve those business of law problems can be really energising for teams, and all the more so where you find opportunities to collaborate with clients.

For anyone looking to get into this space a lot of what we’ve discussed would be super useful for them to understand and apply in their current role, but do you have any other tips you would provide to individuals looking to make a similar transition from a legal role to an innovation role?

It’s a tough question because so many journeys can be quite unique. I think that’s probably part of it — embrace your unique experience because everyone’s got a different perspective, whether that’s the transactional lawyer being up all night trying to juggle conditions precedent checklists and thinking “there has to be a better way” or a litigator building chronologies in MS Word manually and despairing at the umpteenth time they’ve manually entered the time, date and content of an email that forms part of the evidential chain.

You should also add to your experiences. If you’re looking at yourself and thinking, “I’m a four year qualified banking lawyer, and all I’ve done is CPs and churning out the same documents day in day out and generally feeling incredibly specialist in a progressively narrow niche”, you need to make space to acquire alternative experiences.

The other thing to do is to keep records of relevant experiences, or things you’ve done as a lawyer that do have transferable skills to other roles and organisations. It’s easy to forget when you’re working crazy hours the many things you do that really aren’t legal specific, and absolutely transferable to other roles, especially when communicated in the language that other roles ascribe to those skills. Understanding the language that other roles use and joining the dots between that language, the skills it describes and the things you do as a lawyer will help you build out your portfolio of demonstrable transferable skills and experiences.

A good example is transaction management, which overlaps with project management. If you’ve managed multiple interlocking transactions for a client over a longer period for a larger goal, you’ve basically been doing a form of programme management.

That’s not to say lawyers have all the skills, but simply that you can close any perceived transferable skills gap by a good amount by mapping the relevant parts of your legal role to the corresponding tasks or skills of a non-legal role. Talking in legalistic terms will miss the mark even if what you are actually describing is relevant to the role you’re considering.

Know your audience and learn their language!

If there are opportunities at your firm or otherwise where you can express creativity or take your career in a slightly different direction then seize those opportunities. If you have an innovation, legaltech or ops team and they are running initiatives — volunteer! And don’t wait for opportunities — seek them out. Teams like mine relish the chance to work with enthusiastic individuals.

It is going to be quite scary. If you’re a lawyer, you’ve probably sweated to get into the right university, get the right grades on the LPC, get the right training contract, get the right department upon qualification and so on. And then you might be sat there 3 or 4 years into a qualified role… and the thought of sidestepping, let alone completely pivoting is terrifying.

But it can also be liberating.

It’s also worth understanding that the way law is practised today will likely look very different in five or ten years time. If you’re not generally thinking about the future, and how your role — even as a lawyer — might change, then you aren’t going to be well prepared for when those questions do arise as you progress, whatever your role, even if you stick with lawyering.

For instance, on the lawyer side, as you progress you will need to develop a business plan and demonstrate how you can bring new business to the firm, and a part of that will be thinking differently. You really don’t want to overlook that aspect, and end up a clone lawyer, either in your own firm or if you decide to enter the general job market. The more skills and experiences you can develop the better equipped you will be to take a run at the right opportunities as and when they arise, or as you create them.

Getting involved in innovation, whether taking the initiative and rethinking your own legal work or that of your team is a great start, as is working with your organisations existing innovation function.

That’s great advice. Definitely agree it’s worth building out your portfolio of relevant skills and experiences, and there are many great ways to do this around your day job.

Finally, what books, blogs, podcasts or other media would you recommend to readers in terms of what we’ve discussed, careers and so on?

There’s such a wealth of information out there and often it can be overwhelming. For me, on the design thinking side, I really enjoyed Sprint from the Google Ventures Team — when I was first thinking about designing workshops and prototyping, it helped crystalise my thinking.

On the behavioural science side — start with Predictably Irrational by Dan Ariely. It is really accessible and although a little old now, it puts a fun spin on basic behavioural principles. If you want to increase the fun factor, Alchemy by Rory Sutherland and Hooked by Nir Eyal are interesting looks at how behavioural principles interact with the real world. Of course there is Thinking Fast and Slow, Nudge and countless other texts to work through on the popular science side. In terms of podcasts, It’s All Just a Bunch of BS, and The Decision Corner are brilliant fun.

More generally, Start with Why by Simon Sinek is a real touchstone. How often have you lost your way or not been able to articulate the reason behind something? Start with Why!

I’ve been surprised as to how little pieces I’ve picked up from reading or listening to podcasts filter into my thinking months on from the initial interaction. There is a certain joy in letting things percolate and then your mind making the connections to give you a novel perspective just when you need it! The more ideas we are exposed to, the wider our pool of potential approaches, even if you take just the tiniest bit of actual substance from the original point.

⚡ Interested in legaltech careers like Nitish’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

Mary Bonsor is the award winning CEO and Co-Founder of Flex Legal, a platform to connect those in need of legal services with interim lawyers and paralegals for a flexible, on demand service.

Established in 2016, Flex Legal is the UK’s fastest growing legal services provider with over 5000+ paralegals, 250+ lawyers, and 300+ law graduates in its talent pool, serving 350+ clients.

Flex provides a win-win for lawyers/paralegals and clients. For clients, Flex is a high quality talent pool of legal professionals available for times of peak demand or special projects. For lawyers, paralegals and law students it allows flexible working and the opportunity to build experience and gain exposure to different types of client and legal practice on a flexible basis.

And that’s not all.

Flex has recently started offering their own software to law firms so that they can build and manage their own pools of flexible resources.

In this interview we discover how Mary, drawing on her own experiences as a law student seeking work experience, decided to launch Flex Legal. In doing so she and her team have built a different type of alternative legal services provider, uniquely differentiated by its personal touch and tech optimised processes.

Mary, how does your career begin? How did you go from being a solicitor to start-up founder?

I went to Leeds university and studied politics and sociology, and to be honest, like a lot of people, didn’t know what I wanted to do after university!

However, I did know that I wanted to continue my studies and liked the thought of problem solving and helping people. And that is how I fell into law!

I did my GDL and LPC after uni, and while I was doing that, I really struggled to get work experience.

It was frustrating. When I would walk around the city I’d see lots of law firms and would have jumped at any opportunity to get stuck in. But those opportunities were few and far between it seemed, or at least very limited.

Eventually I did manage to land a training contract, joining Winckworth Sherwood LLP, which was next door to the Kaplan Law School.

Whilst at Winckworth I’d see lots of law students passing to and fro and in and out of the Kaplan Law School. It was then, reflecting on my own challenges obtaining legal experience and my training contract, that I had the gem of an idea, which was to find a way to connect law students with quality work experience and other inroads to the profession.

How did you go from that initial idea to taking action?

Slowly. It took 4 to 5 years for me to be brave enough to take the plunge. That came about when I met Jimmy Vestbirk, the founder of LegalGeek, and my co-founder for Flex Legal.

We spent about two years researching and testing the concept around our day jobs on the weekends and evenings, eventually building up to a trial with one law firm and five paralegals.

Around that time we were also introduced to James Moore, our first technical hire.

Was there a natural tipping point when it became necessary to go all in with Flex, or was it more of a gradual transition from your day jobs into making a go of Flex Legal full time?

Getting investment was the tipping point. I didn’t have huge amounts of savings; I couldn’t drop everything and launch into Flex Legal immediately without the support of a salary. Securing investment was the greenlight to leave my legal career behind and give Flex Legal my all.

It was quite a balanced shift. When I left my firm I ended up doing some flexible consulting for them whilst gradually ramping up my focus on Flex Legal. Eventually things ramped up enough with Flex Legal that I transitioned to Flex Legal full time.

Looking back, it was a really nice balance of researching the business problem, testing it, getting the investment and so on, which altogether gave me the courage to give it my full attention. Flex Legal has been growing and growing ever since!

What do you think was behind that early initial growth? Was it a tight fit to an unmet need or was it something completely different?

In many ways what we do isn’t new or novel. Alternative legal resourcing has been around for years and years. But it was the way we were doing it that was original.

We were one of the first in the space to create a pool of law students, both to enable their access to quality work experience, and as another type of resource for legal buyers to procure.

Some of these buyers were legaltech start-ups looking for legal talent to provide domain expertise. For instance, helping build, train and test AI models for contract review technology platforms. This was a really differentiating set of experiences for those law students vs. traditional legal work experience, which we also helped facilitate.

We also focused heavily on a great user experience driven by tech. Our platform made it easy to meet and assess talent. Each individual on the platform had a profile, including a short video to capture their personality and style. When we pitched our platform to people they were blown away by the personal, human touch that we’d added to an otherwise transactional experience common to other businesses. It really helped buyers get to know candidates quickly and easily, saving time on both sides of the resourcing equation.

And we’ve really expanded from there. The engine behind our platform connects everything, automating a lot of our processes such as time sheets and similar. This helps keep us competitive and enhances our value to clients.

This technology is now being used to make it easy for aspiring lawyers to log their qualified work experience toward their SQE (The Solicitors Qualifying Examination, which is a single, rigorous assessment for all aspiring solicitors that also combines a requirement for qualifying legal work experience).

Note: for more on the SQE, see Flex’s excellent FAQ here.

So in that sense our tech is really the means to achieve two goals: the first is to create a human and personal experience when matchmaking between the supply and demand side, and the second is to ensure we are as efficient and cost effective as possible.

We like to think you can’t automate your relationships with your clients and your candidates in recruitment, but you can and should automate everything else in between.

My co-founder James is great at observing our processes and finding ways to continually improve them with technology so they become faster, more effective and efficient.

Having been a client of Flex Legal before, and having myself struggled to obtain legal work experience as a law student, I recall a major USP of Flex Legal was the fact it was open to law students and emphasised finding appropriate legal experience for them. Can you elaborate on that aspect of Flex Legal?

It’s a massive part of our origin and mission.

As I mentioned, I struggled to find experience at the start of my career and wanted to widen the opportunities available to students. So getting law students onto the platform and, more importantly, into quality placements with real legal work experience opportunities was crucial for us. And we succeeded. Our students have done all sorts of placements, at law firms, in-house legal teams and many legaltech vendors.

It’s the best feeling ever when you get messages from people saying, “thanks for helping me secure my first work experience, which led to another and another and eventually into a training contract”.

As of right now we have helped 371 people secure training contracts, and we’ve helped create around 10,000 work experience opportunities for law students that have indirectly led to training contracts or other roles.

Another thing we’ve done recently is provide our Flex Legal Journal free to anyone looking to qualify as a solicitor via the SQE, which requires a detailed set of evidence demonstrating that you have gained qualifying legal work experience at up to 4 places over 2 years. The Flex Legal Journal allows aspiring lawyers to record and reflect on such qualifying experiences and to track progress against the SRA’s competency framework and to share and request the required confirmations of supervisors during such experiences.

What other USPs have you built into Flex?

A lot of ALSPs started off with lawyers first and then added paralegals, whereas we took a different track and did the reverse, starting with paralegals and law students and adding lawyers later.

Our culture and values resonate with our people and customers. Our culture is about being responsive, positive and being human. One way we are able to be responsive is via our technology, but also partly because of our culture of responsiveness.

What were the biggest challenges to launching Flex Legal?

We always tried to bootstrap Flex Legal. We wanted to raise a little bit of money to get going but didn’t want to go down the VC route of raising millions. That was a challenge — you have to get the money in and keep growing your revenue from early on; but that’s a great discipline to have from the start. A lot of start-ups do the opposite, which can work, but can be much higher risk and so wasn’t for us.

Another one of the general challenges is always that you don’t know what you don’t know. When we sent out our first set of T’s and C’s, which we had drafted ourselves, they got torn to pieces by a law firm!

Rather than reacting badly, we expected these events and accepted they are a natural part of the very steep learning curve you climb as a first time founder.

You learn, iterate and improve and move forward through experience.

And on financing, I think you can raise too much money too soon. That can sometimes be distracting or introduce additional decision makers too soon and although can give you a lot of potential press, I always try to remember that “fundraising is for vanity, profit is for sanity” that your idea works.

Another challenge was sales. I had worked in a reasonably small law firm and didn’t have a huge network at the time. I was still relatively new to the legal industry.

But I’ve been, and continue to be, amazed by how much you can get done in terms of networking just by being confident and reaching out to people. It’s not easy, or always comfortable, but if you put yourself forward and be genuine a little can go a long way.

LinkedIn is incredible for one thing. Anyone can set up a business page on LinkedIn, or Instagram or Twitter and so on and with a bit of work, reach a very large audience and contact specific individuals with which to build relationships. It’s incredible what we’ve achieved just through reaching out to the right people.

The supply side of our business — the law students, paralegals and lawyers — is easier to build and manage. The demand side — the clients who procure Flex’s legal professionals — is trickier. Getting into FTSE 250 or 100 companies is a long progress. Finding the right decision makers and fit between them, our model and our candidates requires careful time and attention to create the right relationship. It’s also very similar for getting into large law firms. In either case the sales cycle is quite long and complicated between initial contact and booking revenue with that client.

Sales is definitely an overlooked skill in legal organisations and legal training. It is however, a skillset that is very valuable. At the end of the day you always have to sell at least one thing — yourself — so it makes sense to gain this experience where you can. Is there anything specific on the subject of sales that has helped you develop the sales function at Flex Legal?

Yes, we used a company called Pareto Law, who provide sales training to grads straight out of uni. They’ve been brilliant. From first walking into their offices I was blown away by the welcome and their delivery.

I think everyone should learn sales. If you’re a lawyer, to become a partner you need to sell. When you work with clients at whatever level you are always to some extent selling yourself and your organisation. A key part of that skillset, is listening — people generally talk too much and listen less than they should. Especially lawyers!

For that reason we have rigorous sales training when people join, and a commercial development scheme, or our CDS as we call it. Everyone that joins us is trained in each.

Being more commercial is a key skill to master. It’s one of the big questions you get asked again and again when you are applying to join a firm, or work with one. That was an area with which I struggled when starting out as a lawyer so it’s important to me that we help our paralegals master this skill. To help them do that we involve them and show them how we run Flex Legal, how the finances are managed, how the sales process works, the booking process, the operations and so on. We believe that providing this overview of the commercial cogs in our operation will help them gain hands on experience of commercial activities and skills.

I think this is one of our biggest successes with paralegals who’ve joined us. Every paralegal that has completed our CDS has gone on to secure a training contract, which has been brilliant to see! We have had 28 officially through us and I am determined to help the current cohort achieve the goal too.

That sounds like a great idea. I would have enjoyed getting to see and understand the commercial side of a legal business. In most legal organisations, especially Big Law, the business of law is kept separate from the practice of law side until relatively late in your career.

I agree. When I would be working on a litigation for example, I wouldn’t always connect the dots in terms of what does this actually mean for the business and therefore why it is so important? When you’re busy lawyering you don’t always have the bandwidth or wherewithal to ask these sorts of questions. It’s kind of odd that it isn’t made a more significant part of the job on average because as you become more senior, the partners who are doing very well are the ones who understand their clients’ businesses in great detail and the drivers behind how and why they make their decisions. I think this could be trained into lawyers much sooner and much better.

Thinking about that switch from being a lawyer into a founder role and starting a business, were there any particularly transferable skills and equally, any skills you had to unlearn to succeed as a founder?

In terms of transferable skills, I think lots of lawyers enjoy people and enjoy helping people solve their personal or business problems. In doing so, you develop good communication and people skills, and the best lawyers also are very empathetic. All of these were crucial to setting up Flex Legal and immediately transferable, and remain very valuable to this day.

In terms of things I’ve had to unlearn or adjust, one of the first things I grappled with was rethinking how I felt about curiosity and not knowing things.

As a lawyer you’re often expected to know the answer to everything. When you are faced with the unknown, particularly something entirely alien and new, it can be very anxiety inducing.

I always used to get really nervous when I hadn’t done something before rather than think to myself, “oh, this is a great opportunity. I’m going to be curious, Google it and see what I can learn”.

My co-founder James has been great at helping me develop this skill.

When we first started working together I’d ask a lot of questions about how to do something and James would simply suggest I go Google it, and if, in an hour, I’d not answered my own question, to come back and discuss the problem’s solution.

Unsurprisingly you learn a lot more via that process than simply being spoon fed the answer. It also builds confidence that you can step into new domains and problems and figure out solutions without necessarily being a deep subject matter expert as is the case in legal roles.

Creating an environment at Flex Legal that encourages this mindset has been important to us. I think it’s how you attract, nurture and retain people — by allowing them to be challenged and to challenge themselves in a safe environment so that they are constantly learning and feel energised about doing so. If you’re not learning in a job, it’s often time to move on. We want to make sure the entire team is always learning and growing.

One thing I’ve really noticed from reading leadership books, and something which I really don’t think happens at law firms as much, is the understanding within leadership that to be a good leader you need to understand your employees, what they want to achieve in their life and why. For instance, do they want to one day set up a farm in Somerset, or do they want to get to be a top performing sales person? In either case, if you don’t know this about them, how can you help them and retain them? The answer is: you can’t. You have to take a genuine and deep interest in your employees so that you can manage and lead. If you do so, you’ll help them become the best they can be and that will keep them happy, motivated and constantly hungry to learn more.

Learning how to give really good feedback in this context is also key. If you build the right relationships, the trust and the right environment you can be effective in providing constructive criticism because it is easier to show that you are doing so because you genuinely care about a person’s development, and enabling them to be the best that they can be. Not only that, it does wonders for collaboration and creating a great culture where everyone is pulling in the same direction for the same reasons.

Sales skills as I said, were an area I had to develop and build out among the team. And as I say, sales is something for which lawyers should receive more training and much earlier in their career.

I’d say learning to put yourself out there, to be bold and to reach out to people — to ask them for a coffee and so on — is also crucial.

Getting good with spreadsheets, and Excel generally, has been very worthwhile. I really think lawyers could do so much more with Excel. I’ve gotten so much out of getting better at Excel — it’s saved me a ton of time, helping to automate basic admin and so on.

In addition to learning new skills, how does founding a startup differ from being a lawyer in terms of the activities? What would you say the kind of key differences are in the tasks and responsibilities you have as a founder versus those you had as a lawyer?

As a founder I was doing the invoices, sales, being a COO. You’re a whole mixture of roles early on, and often for quite some time until the team can grow sufficiently.

You need to be curious and get comfortable learning on the job and not always knowing the answer in every scenario, but being prepared to find it out.

Now my role is very different. It’s more focused on management and strategy and less so on the day-to-day operations. I certainly didn’t do any of these sorts of activities as a lawyer, especially not the management and strategy side of things.

As our Head of Manchester once said to me — you have a DJ and dancers, and I’ve probably moved from the dancefloor — as a lawyer — to becoming a DJ — as a founder which is also a challenge in itself. As to scale a business properly, you need to make yourself redundant to a certain extent so it is not reliant on its founders. Going off on maternity leave was a great test of this!

The management and strategy side is a skill I am constantly learning. When I set up Flex Legal it was really about helping people and seeing where it would go… but now Flex is 32 people and we need to think carefully about where we’re going and what we’re doing and our two year plan and five year plan and so on. As part of that I need to think carefully about the team’s career progression opportunities and our culture. These have all been new challenges for me, but hugely rewarding as I’ve worked through them and continue to do so.

How, how have you gone about growing a team? Is there anything you’ve learned along the way that you think would be good to continue emphasizing as you grow?

I think culture is king. We’ve definitely made some mistakes in the past when hiring at Flex Legal. But I think if you get people who fit the culture, your chances of success — and theirs — become significantly higher.

As I think Bill Gates once said, if you hire someone, it’s your job to train them properly or get rid of them. Don’t wait around for them or you to become unhappy with the situation. It’s your responsibility as an employer to own an employee’s development and their fit within the organisation. As an employer you can’t take a backseat in someone’s development.

It’s common sense really. If you go to the expense of bringing someone into your company, to your team, it’s only the beginning of that relationship once they join. You need to nurture them, challenge them and help them develop. If you don’t, why bother hiring people to begin with?

One challenge we’ve encountered as we’ve grown is knowledge management, and generally making sure we have effective means to share and communicate knowledge. As we continue to expand the team it is becoming more important to add structure and process so we can onboard people as quickly as possible. We’ve been finding ways to use tech to help in this effort.

When you think about knowledge management in this context do you mean content and / or process?

For us it’s mostly process rather than content. We spend a lot of time process mapping, which I always find very interesting for what it says about our organisation, where we’re at, and where we’re going.

I say that because whenever you run a process mapping exercise you always find out new things about the way you work, or the way people understand things differently for right or for wrong reasons. These always create amazing opportunities to improve the process and most importantly, the relationships between the team.

In terms of content, the knowledge we prize is knowledge of clients. We embed this knowledge into our processes wherever possible, partly so the entire team can remain up to date with regard to our clients, each interaction and the current status of each relationship.

Do you use a CRM system to track those client relationships and associated knowledge among the team?

We do. We’re actually building one inside our own platform right now. We’ve used a lot of off the shelf solutions in the past and found as we’ve grown that none quite fit the unique way we work. Having our own in-house tech team is great. They can look at the best bits from HubSpot and Salesforce and similar and cherry pick the functionality that best fits our way of working, and then integrate this into our other systems so everything becomes more and more seamless and joined up in terms of information. This also helps keep things lean.

How big is the tech team? Did you find it tricky hiring the right technical talent at the outset and expanding the technical team over time?

The team is 9 currently. It could easily be 18 and we’d still have loads for everyone to do!

In terms of building the tech team, I’ve been so lucky to partner with James. James has previously grown a technical team from one to 300 developers. He knows exactly who and what is needed to build a successful tech team.

This question is one I get asked alot by friends interested in starting a business, which I think underscores that it’s not easy to find the right initial talent, especially the right technical talent able to grow a team.

How did you and James meet? How did James get into legal from a tech background?

James knew a partner at Taylor Vinters that was doing a lot of M&A work for a company at which he worked. Through that experience James realized that there were many exciting challenges and opportunities in the legal space with which tech could help. He felt legal was ripe for intervention in terms of tech and good processes.

From that initial interest James got wind of Legal Geek, and via Legal Geek and Jimmy Vestbirk, James and I were introduced. We chatted through the idea and after a 3 month trial period of working together we all decided it was the right partnership to continue and the rest is history!

The other thing is that we interviewed about 10 people to join as a tech co-founder. Several were very bullish on being able to build our platform very quickly, perhaps within two weeks or less.

Now that was initially very attractive, but we very quickly realised that wasn’t what we were after.

Instead, when we met James, he turned things on its head and said this isn’t a sprint, but a marathon and that he wanted to dig into the problem and the surrounding domain first and understand it before promising a solution. He was very honest that he wouldn’t — and likely we wouldn’t — know exactly what we needed until he got to know us.

I instantly warmed to that. It was refreshing versus the other candidates. James wasn’t promising the earth, but promising he’d get to know us and the problem space first, and to take it from there once he’d understood everything in more detail. I liked this approach because, unlike the other candidates, James was willing to admit he didn’t know the industry or problem in great depth, but wanted to understand this in more detail in order to ensure we built a great partnership and a great platform.

What tips would you give to someone wanting to start their own business, especially from a legal background?

Test your idea cheaply and without the tech, and if you can solve a problem without complicated tech, then do so. If you can solve a problem without using tech, think about streamlining your processes some more before you bring in the tech. Getting good ideas and solid processes down first will make the tech a lot easier, and a lot more impactful than if you try and do things in reverse and launch into a load of tech that might miss the mark entirely.

There’s lots of other interactions that are probably more important than tech, especially early on when you are testing your idea and refining it with users.

Networking is super important. You never know where one conversation will go, or where a person will end up or who they know, and people are so generous with their time for the most part, especially if approached in the right way. There’s no excuse these days — you can find anyone now in LinkedIn, Google or via other social media relevant to your niche. Never feel afraid to ask someone for a coffee or a chat.

And finally — just give it a go. Don’t overthink things too much when approaching people to help with your business, whether it be advice, knowledge sharing, introductions or whatever. Be bold and enjoy getting outside of your comfort zone!

I think so many people say to me “you were so brave to set Flex up”, but I don’t necessarily see it that way. Sure, you need to be brave to approach people and try new things, but I think the most important thing is to think “why not? What’s the worst that could happen?”. Once you start framing things this way, it’s easier to rationalise that if things backfire — little or large — you will often have a solid enough fallback position, which makes it easier to take risks and be bold.

Thinking this way will also help you stay just outside of your comfort zone, where you will ultimately learn and grow most. It’s easier to tread water and get too comfortable, but you won’t be pushing yourself and growing as an individual. My advice is to always try and be challenged, whatever it is that you do!

A related question, what do you know now that you wish you’d known earlier in your careers?

I would have set up Flex Legal much earlier! I wish I had been braver sooner and just got over that. It was roughly five years from the idea to actually taking action and going all in on Flex Legal. Of those five years, we spent around two years doing research in evenings and weekends, and I think in hindsight we could have brought forward our timelines quite a bit. As I said, the turning point was getting investment, which to us was the final proof we needed to charge ahead, but I think we could have reached that point sooner if I was to do things again differently.

Was there any reason why you didn’t do it sooner? Was it simply being younger and not having the confidence and experience that you had some later on? Or was it also something completely different?

I think it was fear of failure. I couldn’t get stuck in until I could get my head around the idea that it didn’t matter if it failed, and the only real failure would be failing to give it a go!

As soon as that changed, my entire thought process switched gears and I said to myself, “right, let’s do this!”.

Did having a profession give you some sense that you had a fallback option if things didn’t work out?

Yes it did. I think if you’ve got a profession, such as being a lawyer or an accountant or similar, there’s always something you can fall back on. It’s a good position to be in.

It’s not like you’re closing that door forever. You can always re-open it again.

I also think things have changed a lot for our generation. More people today are keen to move laterally to go up and down and don’t simply stay in the same organisation or team, or even role, to progress. I think this is more exciting and something more and more people will continue to do.

That’s how it was for me with Flex Legal. I was working my way up one career ladder as a lawyer, but when I started Flex Legal, I was starting again at the bottom of a new ladder — that of being a founder and CEO of a start-up. Right now I’m climbing that ladder, but I am sure one day I will be climbing a different ladder again as things change in my life and career.

We’re all going to be working for longer. For that reason it’s more important than ever to be making sure that you are actually enjoying what you do and building the right sills, experiences and connections every day.

It’s very easy to come out of Uni without a real sense of what you really want to do, and even if you do, it often changes as you get older, experience more things and work in more places with more people. At different points in your career you will have different energies and ambitions — at some points you might want to be a rockstar constantly pushing and chasing the next big thing at work, and at other times you might need to take it steadier for a while. Recognising this is important.

Finally, do you recommend any books, blogs, podcasts, or other media that you found useful or interesting as you’ve transitioned from being a lawyer to a startup founder and building a business?

Yes, lots! I always try and read a leadership, startup or scale-up book every month. I love it because you get different ideas every time you do.

Even if you don’t agree with everything you read, you always pick up some nugget of actionable insight that can be applied to your business and team.

One of my favourites — and one I keep beside my bed for easy reference — is Stephen Covey’s 7 Habits of Highly Effective People. This book has some great strategies for building and maintaining a highly effective personal and professional business life without burning out.

Right now I am reading Measure What Matters by John Doerr, the legendary venture capitalist. Doerr was an early investor in Google, and introduced Google to OKRs, a system originally pioneered by Intel’s Andy Grove as a management technique for aligning and measuring top level organisational strategy and objectives up and down an organisation.

Radical Candour by Kim Scott is excellent. Scott earned her stripes as a highly successful manager at Google before moving to Apple where she developed a class on optimal management. Radical Candor draws directly on her experiences at these companies, explaining the sweet spot between managers who are obnoxiously aggressive on the one side and ruinously empathetic on the other. It is about providing guidance, which involves a mix of praise as well as criticism — delivered to produce better results and help your employees develop their skills and increase success, and building the right culture to support these conversations, which aren’t always comfortable but needn’t be negative.

The Five Dysfunctions of a Team by Patrick Lencioni is a really interesting read about how teams work well together and why. It stresses how being accountable to each other, being transparent and having each other’s backs are the core tenets of what makes a strong and high performing team, and the absence of those traits is what holds a team back.

I find reading books like these is a great way to learn from others; it makes me think outside the box. It also gives me food for thought to challenge James and the team, to get everyone challenging how we do things and why. It can really help generate new ideas and improved ways of working. It’s a great to way to make sure you are constantly learning and not simply standing still! We now have a management team book club so we can all continue to learn and challenge each other as we grow!

⚡ Interested in legaltech careers like Mary’s? ⚡
See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

Steve Wheeler is a lifetime technologist, catching the bug aged 7 when he got his first computer, a Sinclair ZX-81.

Today Steve is CTO of Legatics, and before his current role led various technology teams and on large scale technology projects and products at a variety of organisations, including the BBC and some of the early ISPs that later went on to be merged or acquired into the major ISPs we all use today.

If you live in the UK, there is a very good chance you use technology that Steve has worked on, whether it’s your ISP or BBC News.

As a newcomer to the legal industry and the legaltech technology niche, Steve brings a wealth of experience and insights from outside the legal bubble and is excited to share his experience and help scale and extend Legatics. Although Steve is new to legaltech, he isn’t new to start-ups, having also previously helped launch a fintech business, CrowdBnk.

Let’s dive in!

Take us back to the start. Where does your career begin?

My interest in technology began aged 7 years old. My mum worked as a Senior Systems Analyst — the first female one — at a crane company, working with the English Electric KDF9, an early British computer, and my uncle was a lecturer in computer science at Teesside University. So I always had a strong tie to IT.

It was my uncle who gave me my first computer when I was around 7. It was a little Sinclair ZX-81 computer that had to be plugged into the TV, which meant I couldn’t use it all the time!

Because I couldn’t use it all the time, it was in those early days a real treat to use it. At the time there wasn’t lots of packaged software or games. It meant copying code out of the backs of instructions manuals or magazines and poking away at that code to make it do different things, and then gradually working out what was going on and being able to build things myself. I enjoyed reading and hacking with things, so I got a lot of enjoyment out of this.

I was also lucky with school. I had some really excellent teachers who supported computers in the late eighties to mid nineties. They really let us go beyond what was in the curriculum and mess around much more freely on the computer network at school than they probably should have!

One of my first school related projects — part of my GCSEs — was trying to build a vet management system for my local vet after my sister and I got some gerbils as pets. It worked well and had quite a nice user interface that I’d had to build from scratch but it ran on a Commodore Amiga and wouldn’t really have been ready for real-world use.

As I got older, I spent time around my degree at the University of Leeds working for Electrolux, Berghaus and the Halifax bank on the side, so by the time I graduated I had a fair amount of experience dating back a long time, plus some commercial experience. I think that was helpful to stand out a bit from the crowd when looking for my first full time job.

Around graduation in 2000 I realised I wanted to learn more about the internet, which was really starting to take off — though also heading into the first dot.com bust at the time.

Against that backdrop, although I had a lot of computing experience and had used dial-up internet for a few years, I wanted to understand more about how the internet worked. As an example, at the time your modem could dial a number in Newcastle or one in Northampton or Nottingham, and you’d get the same connection — your data would go from and to the same place — which went against the way I thought it worked. So I decided I wanted to find out how that could happen.

So my first job after uni was a tech support position at an Internet Service Provider (ISP) called Planet Online, which became Energis and eventually a part of Vodafone. At the time, it was the biggest business ISP in the UK — something like one third of the UK’s internet traffic went in and out of their network.

Tech support turned out to be a great way to speak to customers directly and learn about their problems, solutions and how they were experiencing the internet and their challenges getting early websites and other web services spun up. Often this was big customers, such as Jungle.com (a sort of early UK based Amazon type business). Speaking to lots of people didn’t come naturally to me — actually I dreaded it at first — and tech support probably isn’t a role Computer Science graduates often target, but as a first career step I think it worked out well for me.

Planet Online, or Energis as it became whilst I was working there, was a really good place to learn a lot about the fundamentals of the internet. A lot has changed since then, but the fundamentals remain the same, so it’s served me well in my career as the internet became more and more pervasive and important.

From that role I moved into a team called Core Systems, that built and maintained the systems underlying third party ISPs like Freeserve, which was a virtual ISP — an ISP that resells the resources of existing ISPs, such as Energis’ resources, under another brand name. Core Systems was a strong, tight-knit team with some really great technologists — a lot of the culture and thought processes from those days are still with me now, and it taught me the importance of building systems that can be managed and maintained over time as teams and priorities change.

Whilst I was working in Core Systems, hardware wasn’t powerful enough to run a database for such a big product as Freeserve became, and inevitably my work was heavily focused on optimization so that these systems could handle ever increasing demands. This set of experiences proved useful to my later career working on highly scaled systems, such as at BBC News and their elections coverage.

In my Core Systems role I learned how to quickly build trust between the Energis and Freeserve teams, who to some extent had some healthy rivalry as ISPs, with the latter leveraging the former’s resources under its own brand.

Eventually, Freeserve — by that time part of Wanadoo — hired me. One of the first major projects I was involved in was the further re-brand from Wanadoo to Orange, which had acquired Wanadoo to be its ISP division.

Around that time I took on a new role, as a solutions architect on the broadband and mobile telecoms side of the combined business, which was great. I got to spend a lot of time on an IPTV product, a service similar to Sky’s video on demand service via a managed network, which is much less common today vs. over-the-top content (OTT), the type of internet TV service you get with iPlayer, Amazon Prime, Netflix, and so on, accessible on any device.

A busy time for takeovers! Can you tell us some more about the solutions architect role and how it differed from your prior roles?

I was a solution architect in the internal facing sense and not in the sense of facing the end users of the product. It was quite challenging at first, partly because I was and looked very young, so I had to develop confidence in myself and my role and exhibit those qualities.

I got to travel a lot in the role, especially around the UK and France. France had a more hierarchical business culture, and perhaps a little more siloed in how teams and individuals were organised functionally. That made it more challenging from a stakeholder management perspective, but not overly so. It was good to have that experience and to understand how different cultures work differently.

The main purpose of the Solution Architect role at the time was to build a path and a plan, from a business need to technology solution. In a complex business like Orange that could involve bringing together anywhere between 2 and 20 teams, each owning a part of the technical estate, and leading them to deliver the overall programme of work. As with many technical leadership roles there was a balance to be struck in terms of how far the architect should be involved in a given team’s activities and where they, as the experts, should be empowered to do what they felt was right.

Working alongside project and product managers made things a lot easier in terms of managing the various stakeholders and the creative tension between technology, product and delivery is always valuable.

Just on that point, one challenge in legaltech is that a lot of legal organisations have “legaltech” or “innovation” related roles that shoehorn about 5–6 different roles into one FTE, including things such as project or product management, which are individually expert and professional disciplines.

Do you think it’s preferable to have teams with specific individuals fulfilling specific functions, and ideally experienced professionals in those domains, such as project or product management vs. trying to have one person be all things to all people?

Yes, it doesn’t make sense in my opinion, and based on my experience, to cram these different roles onto one person’s shoulders. Having knowledge of other disciplines is always useful and there’s the view of the T-shaped person being an ideal — someone who knows at least a little about a lot of things but specialises in and focuses on their own discipline. But diversity in knowledge, approach and perspective is valuable and none of that is available if one person wears all the hats.

Speaking of my own experience in technology leadership roles, it never makes sense for me to do all things. To me that is not successful technology leadership.

Successful leadership — whether technology related or not — is about enabling, empowering and guiding those around you and creating an environment that supports that.

A lot of that is about communicating the parameters in which the team and the organisation makes decisions and the business drivers that sit behind those parameters.

So after your time as a solution architect you join the BBC and launch an online banking start-up, CrowdBnk on the side. That must have been pretty hectic! Can you tell us some more about those twin tracks?

CrowdBnk was a project started by a colleague and friend from Freeserve who did an MBA and decided to launch a new online business.

The idea was to provide debt or equity finance for small to medium sized businesses, largely funded by high net worth individuals. It was basically crowdfunding, but obviously different from models adopted by Indiegogo and Kickstarter aimed at funding from anyone and everyone for all sorts of projects.

It was a bit of an adventure. I didn’t really know what to expect. I didn’t get into it assuming, or requiring, it would be wildly successful — I simply got into it because I was excited to be a part of it.

My role was principally around helping design and organise the product and technology build so that it could scale and operate at an enterprise level. It was great being able to move so quickly, and to make technology decisions from virtually a clean slate.

And you were juggling Crowdbank alongside your full time role at the BBC, initially as a senior technical architect / engineering manager, and later head of software engineering for BBC News?

Yes I was full-time at the BBC and doing Crowdbank outside of work. Early on at CrowdBnk we’d also hired some full time developers, so this allowed me to dial back my direct involvement except when we had problems or were building big new features that required much more of my supervision or advice.

I was very busy at the BBC when I joined. We were having to get the elections coverage systems ready for the upcoming political elections. The system they had in place had been around from the very early 2000s and had been extended and amended numerous times, but as we approached the 2012 US Presidential election it became clear it needed a rewrite.

To do that we started building a new elections system in AWS, which was my first experience with AWS. It was also very new to the BBC, we had our team in news and one team in iPlayer sort of racing each other to see who could launch a product in AWS first.

We had a lot of challenges, but we got the election results out on the night.

The one thing with elections systems and the coverage is that if you’re late, if your delivery date slips, you may as well not bother. You can’t ring up the government officials to delay the elections or the results as they come in! You’re either ready, or you’re not.

From a societal perspective, it’s also critically important you show the right results and deliver them to people in an engaging and accessible way.

So it was a stressful, but exciting opportunity and one I really enjoyed.

Although it’s easy to think the modern up to the minute coverage is new, it is surprisingly long standing at the BBC. There’s some really interesting footage dating back to the 1979 election and before, where the BBC have the results being rung up on systems similar to a Cricket Scoring Box, using paddles to flip the vote tallies up as they come in.

How did it compare working at what became Orange, and at the BBC? Both are very large organisations but obviously quite different in their histories and purpose.

They are quite different.

The BBC is a big organisation, but it doesn’t always feel big. It’s not like I knew every one of the 25,000 or so people that worked there when I did. But different teams and product areas were relatively tight-knit. It’s also worth bearing in mind that the vast majority of the BBC’s resources go into making content rather than into technology — content is the core business and a lot of hugely passionate and knowledgeable people make it what it is. But there’s also a long and strong history of real technology innovation at the BBC, going back right to its founding. They really have driven the state of the art forward.

At Orange, there were obviously lots of different teams and there was some content production too (Ananova, anyone?) but mostly my role meant I was moving between teams on different projects, whereas at the BBC I was working on a particular product set and with that division most of the time, i.e. the News group, which included Weather and the World Service.

So the main difference between working at either organisation was my really my role, on the one hand more projects based at Orange, and on the other hand at the BBC more product and domain focused.

Do you think there’s pros and cons to being more of a specialist vs. a generalist?

I would say that in technology you can have a successful career, either as a Jack or Jane of all trades, or as a deep specialist.

I’ve ended up more the former, which wasn’t originally the plan but which I think has served me well in my later technology leadership roles. It also preserves a wider range of options, which may — depending on your personality — provide a degree of security and excitement vs. being really good and one thing, albeit some people find security and enjoyment doing just that.

If you are a deep specialist, that can make you very valuable. But if your specialism suddenly becomes no longer necessary, you can quickly be in an uncomfortable position, both with your current employer but also with the broader market of other employers. In that scenario, options might be limited absent of a reskilling exercise. I’ve seen that affect people most where the specialism is around a particular set of business tools or perhaps internal platforms, which never last forever, and it’s something I keep in mind for my own future.

There is also always a premium paid for people who can work in the cracks between different teams and specialists, as translators or bridges between these domains. So that is another reason being a little more generalist, or specialist in several areas, can be a benefit in terms of careers.

Fastforwarding to your new role, as CTO of Legatics, an online deal management platform popular with law firms and banks, what drew you to the legaltech niche? Did you know much about it as someone working in general technology beforehand?

To be honest, I didn’t know much about the legaltech niche until I started chatting to Legatics about the role.

Legaltech isn’t really any different to any other tech, but what I would say is that when I got to know the Legatics platform I thought it makes perfect sense that such a thing exists for legal professionals.

It is pretty clear to me now that for a lot of legal work there is a strong, fairly standardised workflow element, especially for junior lawyers. And so it makes sense to use technology to streamline these processes where possible.

In terms of what drew me to this sector, it’s less sector specific, but the objective challenge and opportunity it presents.

I really enjoyed the BBC and have enormous fondness and respect for the organisation. It can be a tough place to work at times but I learned a huge amount, worked with great people and had a great boss — I knew it would be a tough act to follow, and am very proud of the work my team and I accomplished there.

But when I started thinking about a new direction there seemed like two options: a large company or a start-up. I wasn’t minded to explore related industries to BBC and telecoms, partly because I didn’t want to get typecast and saw no reason why I should be.

So it was really the content and opportunity of the role, and about what I was going to learn and how I could develop myself, rather than the title or company name to work for.

And my new role at Legatics ticked those boxes.

Before Legatics, had you had much experience working with lawyers and other legal professionals?

A little. I’d been involved in various procurement activities at the BBC and Orange, a tiny bit of what I think you’d call M&A, and have dealt with lawyers in my personal life, e.g. when buying a house and so on. And of course, I got to know the Legatics founder, Anthony Seale, as part of the hiring process.

Through those discussions with Anthony, including about typical legal transactions such as financing a power station or similar — firstly it sounded horrible for the people doing these deals manually, and secondly it was very clear how technology could make a big difference to those individual’s wellbeing and their firm’s productivity.

I did think going into this space that a lot of the activities involved in legal transaction management would be undertaken by project managers, rather than someone specialist in law. So it surprised me that the repetitive assembly of documentation and other process steps were being done by lawyers. It seemed a bit mismatched from a skills and experience perspective and actually I thought it must be a disappointing bump for a new law graduate landing that first associate role.

That’s not to devalue project managers in any sense, quite the contrary — a good project manager is hugely valuable and can make a massive difference in all sorts of ways. They are arguably more skilled and effective at project management because that is what they are trained in and where their experience lies, versus lawyers who aren’t trained in proper project management methodologies and similar yet expected to muddle through using a Word table and email.

It seems odd the industry doesn’t value project managers in quite the same way most other industries do. Use of project managers would free up lawyer time to help them focus on the legal specific parts of these transactions, e.g. the negotiation, advice and specialist drafting etc — the things they are really good at, and enjoy.

What do you see as the most exciting opportunities in your new role?

I’d say getting my feet under the table and getting to know the industry is exciting.

The legal space is much less familiar to me than the world of online news, broadband and mobile systems which I interact with everyday as a consumer, and obviously spent a long time working on in prior roles. So a lot of my time is going to be spent initially learning more about the legal systems, our customers, and how the Legatics platform is being used day-to-day.

The most exciting thing is that Legatics is a great product. It’s really well-built, and backed by an organization that has a whole bunch of talented people who were lawyers, who’ve had the poor experiences we just discussed trying to manage deals and who are genuinely invested in solving these problems and making the lives of legal professionals better and helping them to deliver outstanding client value. I’ve been really impressed by the work ethic and professionalism of the entire team.

It would be great to make Legatics the landing page for all legal business within transactional teams. I can see a path to that outcome.

I’m going to be spending time helping us scale the platform, and adding more developers to the team to help with that objective, especially as we increasingly widen the customer base.

We have some experimental AI capabilities we are weaving into the platform. We’re not an AI organisation, and deliberately avoid that label. For us we are trying to find subtle but powerful means to apply targeted AI capabilities where it can make a big difference to the workflow and productivity of users in the platform. I’ve not worked with AI technologies before in any great depth, so this is particularly exciting for me to get into and help build out as it’s something I’ve been keen to explore for some time.

What career advice would you give to people, including anything you know now that you wish you knew earlier in your career?

I’d say look for roles or opportunities to take on meaningful or complicated problems and the time to make them good, and make them happen. Show that you can get things done. Opportunities aren’t handed out, but taken. You’ve got to find them and then take them.

You need to be humble, and not be averse to doing the monkey work where necessary, especially at the start of your career or a new role. But equally, don’t feel that sort of thing is beneath you, whatever level you are at.

Variety has served me very well, but might not suit everyone. I think it’s good to get involved in a lot of different things.

When I was growing up I was a bit of a shy geek, bullied a bit at school, so I wasn’t particularly outgoing or talkative. So working with the great teams at Energis and Freeserve and interacting with a lot of people in those roles made a big difference and gave me confidence and a lot of the skills that were valuable later into my career. It’s definitely worth consciously getting outside your comfort zone.

As a technologist coming into the legal industry from outside, do you think lawyers should learn to code?

I would never tell someone not to code, but I’d suggest they be sure why they’re doing it, or want to do it.

You know, is it that you think you can do better than the coders in your organization? Are you going to be straying into their lane, standing over their shoulders or telling the boss they’re doing it wrong? Is that going to be a productive thing to do in that sense? Where do you want these skills to lead?

If you are going to code, are you going to spend enough time learning to code that you’re good enough and experienced enough that you’re helping, rather than hindering processes that involve development?

Product is again an exciting discipline and there’s some great career paths around product. Maybe as a former lawyer with some technical and product skills under your belt, you can become a great product manager for legaltech applications — and then beyond, if that’s where you want to go. But you really need to commit to learning how to be a product manager, simply being a lawyer that has done some coding isn’t likely to be enough, though it’s a start.

Even if you take some time out and do a 6 month full-time coding bootcamp or similar, you will need to expect that you’re competing against a lot of individuals with significantly more experience, so you will need to consider taking an entry level developer role initially if you want to go down a purely technical route. That said, you may well be able to progress quickly as your technical knowledge grows, because of your prior experience and skill.

I think that’s worth stressing, simply to manage expectations.

As I say, things like software development and product are high-skilled disciplines with a huge body of knowledge and continuous evolution, much the same way as law is — you can’t simply swap hats and expect to land into a senior and influential role straight away. That shouldn’t discourage anyone wishing to tread that path, but more something to be cognisant of before making a big decision.

I’d agree. A lot of developers, like you, have been coding since they were quite young. Not always, but quite often that is the case. They also have a real passion for it. If you are a lawyer and complete a few hours of a coding course, let alone a 6 month coding bootcamp, you will still be much more junior in experience than the average career developer. Being self-aware of that is a must if you’re career changing from say law to development.

Lastly, do you have any books, podcasts or other media you’d recommend regarding technology, start-ups or careers?

I like podcasts a lot, but I tend to listen to international relations and politics. There’s a group called Deep State Radio, which gets some great policy experts and is worth a listen if you’re into that domain.

I’m also a big fan of Reddit, HackerNews and Lobsters. HackerNews can be a bit of an odd community, but it does have a lot of interesting content. Reddit can be a bit unwieldy, but there’s a ton of interesting information and discussion on there amongst the noise.

Newsletters are another channel I enjoy. For a while it was written off as a media category, but seems to be making a comeback. Some newsletters I’d recommend would be:

• The Silicon Valley Product Group founded by Marty Cagan is a great product management resource, and he also has a product book out at the moment, Inspired: How to Create Tech Products Customers Love.
• TLDR Newsletter is a great daily newsletter with links and TLDRs (summaries) of the most interesting stories in tech, science and coding.
• Pycoders is a great weekly newsletter for anyone interested in Python development and various topics related to Python.
• CTO Craft and StaffEng are great resources for engineering leaders — not just for CTOs. CTO Craft has a really strong community, especially in the UK, and recently held its second conference

⚡ Interested in legaltech careers like Steve’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

Should lawyers learn to code? Well, Sam Smolkin did, built an enterprise app — Office & Dragons — and a growing customer base of law firm clients.

From humble beginnings, paying his way through college, Sam ended up as a private equity M&A lawyer at Kirkland & Ellis before launching his own start-up.

But it was an early interest in, and experience of, engineering that made Sam see legal processes differently.

For Sam, legal processes have too many repetitive manual steps crying out for simple yet powerful automations. Absent of targeted automation, these task types are inescapably time-consuming, often written off by lawyers, and demoralising for junior lawyers.

Yet they persist. Sam thought there must be a better way.

Hacking away during weekends and evenings, what started as a side project to automate his most boring legal tasks quickly morphed into the kernel of a business idea that he later validated via a variety of means before launching a start-up.

Sam’s story is a real-life example of how blending engineering and legal skills can allow you to reimagine legal work and find out ways to reduce waste in legal processes and improve productivity through targeted use of tech, creating great value for lawyers and their clients.

Take us back to the start. How and where does your career kick off?

My first proper jobs growing up in Michigan — the auto manufacturing capital of America — involved working night shifts in auto parts factories. My dad is a manufacturing engineer, so he set me up. Compared to the other jobs you could have as an 18-year-old in Michigan, it was actually relatively good pay.

Alongside working in auto parts manufacturing, I attended community college, which for non-US folk reading this is a cheap university you can attend without needing to get any kind of good SATs (entry exams) or anything like that.

My first two years of studies for my bachelor’s degree were done at community college, whilst living at home and working in an auto factory.

I saved money and paid my own way through college, so that’s what really got me started. Eventually I transferred to the University of Michigan, which is a well-established university in the States.

Working in an auto factory and studying at community college is something people usually find surprising given I later end up as a corporate lawyer at Kirkland & Ellis, which is pretty far removed from the experiences of many of my former colleagues.

What did you study before your JD?

I started off studying chemical engineering because I thought I would be some sort of engineer like my dad… but I got seduced by the dark side of liberal arts. I was a typical edgy teenager and into philosophy and that kind of stuff.

Or at least I thought I was.

The idea of not just doing math and science, and instead also doing some linguistics and philosophy was pretty appealing. Somewhere along the way, I got really into linguistics.

That led me to spend two years as a research assistant for a professor in computational linguistics, which is the science behind natural language processing. That was my next serious work experience. I helped with ordinary research, but I also spent a lot of time designing and running the North American Computational Linguistics Open Competition. I worked with faculty from universities all over the world to write computational linguistics puzzles for middle and high school students who, frankly, were much smarter than me if they could solve all of them!

Bizarrely enough, one of my linguistics professors seeded the idea of becoming a lawyer.

He said, “if you like analysing language but want to make a lot of money from it, you should try being a corporate lawyer.”

At the time, I didn’t really know what a corporate lawyer was, but I thought I’d look into it.

Needless to say, he was right about the money, but not so much about the analysing language, or at least not in the sense I enjoyed when studying linguistics.

So did you finish up your undergrad and do a JD?

Yes, I ended up going to Harvard Law School for my JD. In the meantime, I was also an LSAT instructor as well: the LSAT is the entrance test that you take in the US to go to law school.

While I was in law school, it was again, kind of an interesting path. I didn’t have much of a concept of what different jobs were out there within law.

In American law schools, or at least Harvard and similar, during your first summer you can do legal work pro bono, and the university gives you a stipend to do that throughout the summer. Into your second year, it’s all about getting internships at a Big Law firm.

I did something a little different for my first-year stint. I worked at the European Bank for Reconstruction Development (EBRD) in London.

That must have been quite an exciting and unusual experience for a student?

It totally was! It was really awesome. It’s a great organisation. I got to work with a great team of people, and it was my first time living abroad. I really liked it.

London in the summer is loads of fun, though everyone did tell me, that you shouldn’t ever make a decision about moving to London if you’ve only seen it in the summer because the winters are awfully long, grey and wet, but I thought, you know, “how bad could it be?”.

It was that opportunity that got me excited about London and why I eventually moved to London.

After the EBRD, before the start of year two of my JD, I did my interviews for internships with Big Law firms.

I liked London so much I decided to take an internship with one of the UK firms that toured the Harvard campus. That firm was A&O.

I got to spend my second summer working in the international capital markets team in London and in Moscow with A&O. I am a native Russian speaker, I had a connection to Moscow.

I loved the experience, and during my time there I got to do some derivatives work, which I thought was really cool.

I also did a lot of prospectus review work, your regular ECM (equity capital markets) and DCM (debt capital markets) relating to Rule 144A review work and so on.

Unfortunately, I didn’t find that particularly engaging, but it was useful as it made it a lot clearer to me what the job would be like, and which area of law I thought might suit me best.

Meanwhile a friend of mine had gone to the private equity M&A team at Kirkland & Ellis in London and was raving about his experiences there. Now he’s a partner there, and he continues to love it.

I started to think maybe there were other avenues within law I’d like to explore.

And did you start angling toward that track?

Not immediately. I actually took a gap year. Being a good entrepreneur, I was always looking for various ways to game the system to my benefit.

This was particularly crucial for me. Being at Harvard with its large American school fees and my humble beginnings, I had to take on a ton of debt every year to attend, but they also have financial aid, which was pretty generous in my case.

So, I was getting a lot of financial aid, but there were quite few catches. One of which is that for any Big Law internship in your second year you will generally be paid a first year associate salary for the summer, which is great. But this reduces dollar for dollar any financial aid you receive in the following year.

I sense a loophole coming. What did you figure out?

Well, the financial aid programme only accounts for your immediately previous summer and any earnings made during that period. I started thinking… “what if I took a gap year after my internships?”

I asked the financial aid folk about this and they said, “if you did that, we wouldn’t consider the internship earnings from the year before; we only account for the immediately previous summer”.

So that was my greenlight to take a gap year. I took my summer associate money and went on a world tour, which was awesome.

That’s very clever. Where did you go on the trip? What were the highlights?

I went to visited something like 40 countries in Europe, Africa and the Middle East. But the highlight was my time in East Africa, and especially the month I spent in the Democratic Republic of the Congo, trying to cross the country by land and riverboats.

The riverboats I took were crazy amalgamations of humans, chickens, monkeys and all sorts of goods. It was eye-opening to someone who had never travelled much beyond the US and London.

At the end of the summer, I did a non-profit internship in Tajikistan, which was very far away from anything I’d experienced before or since.

So yeah, it was a really fun year. And a smart decision financially.

And where did you end up after returning from your travels?

I went back to law school and finished up my JD.

My aforementioned friend introduced me to the partners at Kirkland & Ellis, and I got a job there, flying out to London very shortly thereafter to be a private equity M&A associate, where I stayed for about three and a half years, including a secondment to New York.

Given your mixed interests, did you get to do anything unusual at K&E?

At Harvard I’d cross-registered for various courses in advanced finance, statistics, linear regression and similar. That, plus my background in chemical engineering and general interest in finance meant I ended up doing two levels of the CFA exams whilst I was at K&E, which is a qualification that asset managers and similar pick up.

I naturally got really good with Excel, which unsurprisingly — or maybe surprisingly depending on how you look at it — made me valuable at K&E.

I was the guy who could understand how to read, and build, financial models that pertained to our PE clients. And I could also translate these into legal docs and vice versa.

Most lawyers will only understand the basics of Excel at best, so I was an unusual breed to my peers.

It was a great experience being invited into a partner’s office, them stepping out of the chair and inviting you to sit down and analyse their client’s spreadsheet and explain it to the senior lawyers on the deal.

I think there’s something junior lawyers could learn from that.

My advice is to invest in wider skills and experiences beyond your legal training. I know that’s harder in the UK where education, including legal education, is more linear, but definitely try to invest in other skills that make you stand out from the crowd and add some edge to your value.

Everyone in Big Law has legal skills. Try and find your unique selling point, some other skills or experience that make you stand out above the crowd. Sometimes it’s being good at stuff other folks avoid or aren’t good at, like Excel!

You’re a rare breed, a lawyer who can code, and rarer still, has actually built an enterprise application. How did you get into computer programming?

I studied computer programming back in my early days of college and university, especially when I was studying engineering and working as a computational linguistics research assistant.

However, I really got into computer programming around the time I got interested in crypto, sometime around 2017.

As I learnt more about crypto I came across the phrase “smart contract”, which sent me down a massive rabbit hole of resources explaining how code is law and that coded contracts would supersede regular contracts and so on.

That led me into learning how to write smart contracts in Ethereum.

And then from that I got drawn into computer science, i.e. the science behind how a computer actually works at a much lower level, but also how algorithms are designed and optimised.

I got really nerdy and was spending a lot of my free time learning, watching lectures, reading books, experimenting with algorithms and so on while I’ve continued to work as a corporate lawyer.

Did this influence how you thought about your job as a lawyer?

It absolutely did. I started to notice how my jobs to be done as a lawyer and my jobs to be done as an open source programmer overlapped.

For instance, in either case I was usually trying to take some complex system, whether it was a software or a deal, and I was trying to capture it in writing, whether that was source code or human language. In many ways, contracts are the operating system for how a commercial relationship is meant to behave and be governed.

But, as a software developer, I had access to these principles, paradigms and tools that made my job so much simpler, faster, and easier when dealing with, to be frank, a lot greater complexity than I was dealing with in my legal work.

By comparison, as a lawyer I’d be sitting there typing stuff into Microsoft Word, word by word. I would often have to open two or more documents and almost always make the same — or very similar — change multiple times within a document and often also across several documents. This was both when creating documents but also when updating or correcting them throughout a deal.

But the only way to do these things in my legal role was to open these documents, wait five minutes while they are opening, and manually make each change multiple times one by one by one… It took forever, was really dull work, you never learn much from this sort of thing either.

As dull as it was, this was the starting point for an idea combining my legal and software knowledge.

Partly it was also borne out of the idea in software that you don’t repeat yourself, and instead keep your code DRY.

By this I mean that when you write software you are always looking for ways to reduce repetition, replacing it with abstractions or using data normalisation to avoid redundancies. In other words, not working the way most lawyers work.

And is this how you started to generate the idea for what later becomes Office & Dragons?

Yes! I kept thinking:

“Surely there is a better way; it’s just data being transferred back and forth, and that means there must be a cleverer process and a way to tell my computer to carry out that process on my behalf so I don’t spend my evenings and weekend essentially doing legal data entry type tasks.”

So, on my weekends and evenings, I started hacking away at the problem.

The day I got things working was extremely cathartic.

I ran some dummy docs through the prototype that were representative of my day-to-day legal docs and tasks and… it worked!

It was such a great feeling.

Coding is very rewarding like that. When you solve a problem, you feel awesome. Coding is also very unforgiving — sometimes it’s crazy hard to unpick why something refuses to work the way you intended, or totally fails.

But once I solved my problem and found a way to automate these types of boring legal tasks, I was super excited, but also felt a little dumb that my colleagues and I — and peers elsewhere to be fair — were wasting so much time doing this type of thing manually, and that it was just the accepted way of working. Nobody was curious or challenging the status quo.

To be clear, I don’t think it’s necessarily deliberate, but simply ignorance borne out of the fact this type of thinking and experience is in no way part of legal education and training, both at university and on the job. Hopefully someday it will be!

This is when it started to feel like my germ of an idea had legs; that I’d like to transform what I’d built into an actual product I could show even my most tech-phobic colleagues, and get them excited about what it could do.

It’s worth bearing in mind that at this point I was the guy in the office who would come into your office, unsolicited, and talk to you about how smart contracts are going to replace regular contracts and how you should learn to code etc… and everyone probably found me very annoying!

In all seriousness though, I wanted those same people to look at what I’d built and say, “wow this is obviously a way better way of working that’s easy, quick and saves me a ton of time and delivers great client value”.

That’s when I decided I should make a UI, because at the time, what later became Office & Dragons, was a command line tool.

How did that go? How did you coin the name?

Well, at first it was still command line based but took on a wizard driven approach where it would ask if you wanted to do A or B and you could answer “yes” or “no” to drive the process forward in whatever direction you desired.

I didn’t want to call it a “wizard” per se, but I liked the fantasy emphasis of the word “wizard” and decided I’d call it a “dragon”, a dragon guided app. The dragon got me thinking “Dungeons & Dragons”, and when I was up late doing the kind of work the app was made to automate, the office felt like my dungeon, so I coined the name, “Office & Dragons.”

How did things develop from there?

It was gradual.

At first, I was hacking away on weekends and evenings when I wasn’t worn out from my day job as a lawyer. Once I got a good working prototype together, I started to think more seriously about the fact I knew several colleagues within K&E doing the same sorts of tasks manually that could probably benefit from what I’d built.

And when I got to that point in my thought process, I got to thinking: which other lawyers might use it?

As such, I reached out to folks at other firms and local counsel firms I’d worked with on K&E deals, showed them what I’d built and asked them whether they would use it on their work and where it would fit, if anywhere, in their process.

Very quickly I got a sense of the threshold features Office & Dragons would need to make the grade for large law firms.

Time and time again, the suggestion was that Office & Dragons needed to integrate seamlessly with their document management systems (DMS), which for most firms I surveyed was iManage.

I heard that enough times that I decided that was what I needed to do, to add that integration… but how? And where to find the information?

To find that out I went to the iManage site and found they had a partner program. That program has a contact form and so I figured, “what the hell, why not?”.

I filled it in and sent them a little email, pretending Office & Dragons was already a business, and enquiring about becoming a partner and integrating with their platform.

I wasn’t really expecting much, but I thought, “don’t ask, don’t get!”

Luckily for me, and somewhat shockingly, they replied a few days later! They asked me to put together a datasheet on the product explaining what it was, what it did, how it would integrate and so on and the value it provided.

At the time I still hadn’t created a graphical user interface, or any front-end for a non-technical user. Everything was still done via a simple command line interface.

iManage were actually interested, to my surprise, and said they hadn’t seen something like this before but that they liked what they saw and thought it very useful.

And thankfully they approved Office & Dragons as an integration partner.

I was even more shocked by this point — I totally wasn’t expecting that response. But it was a massive proof point for me, being accepted into iManage’s partner program, which meant a lot as iManage is one of the biggest legaltech players and used by most law firms and large legal teams.

Did you know much about the legaltech market before this point?

I did not! I thought there wasn’t any legaltech at the time. That sounds bizarre, because obviously I was using a lot of tech to do my legal job, but I just didn’t equate the two necessarily, nor really appreciate some of the legal specific tools I just took for granted.

I thought I was the only lawyer who wrote software. Obviously, we hadn’t met yet! Nor had I met the other folks who I’ve since gotten to know who are lawyer coders or even career changers from law to development and similar.

I got curious around this time and one day I started Googling things like “lawyers who code”.

Coincidentally, LegalGeek had started a series on that very subject, and I came across their blog series and started to discover there were more people like me who were lawyer coders, of which you were one.

That led me to discover LegalGeek and its events, which I was excited to attend. Luckily, they offered free start-up tickets. I emailed them, pitched my soon to be start-up and they gave me free tickets.

As part of that I was invited to spend a week working at Barclays Eagle Labs, the legaltech incubator of Barclays Bank.

I decided to stop by during the week LegalGeek was running and was surprised to see so many major law firms — including Magic Circle, Silver Circle, and a handful of US Big Law firms — backing the initiative, and the number and variety of start-ups and scale-ups being incubated.

My initial impression was also that “hmm, maybe these are more scale-ups and I am way too small right now,” but I got talking to Shara Gibbons, LawTech Manager at Barclays Eagle Labs, and she encouraged me to apply anyway and see if I could become a resident start-up.

A short while later I was invited to pitch Office & Dragons to the Eagle Labs partners — all innovation, legaltech and ops folks from Barclays and the partner law firms, plus others from the Law Society and LegalGeek.

And they said “yes.” I got invited to become a full resident of the Eagle Lab. It was a little nerve wracking but worth it.

Around that same time, I also had the chance to show K&E’s CIO Office & Dragons when he was visiting London and he responded very positively to it, which was a big confidence boost.

So was it these various proof points — the iManage integration partner approval, being accepted into Barclays Eagle Lab, positive feedback on the product from various lawyers and K&E’s CIO — that gave you the confidence to consider making a go of Office & Dragons full time?

Yes, it was that combination of proof points. After that, I decided to go into my boss’s office and say, “well, it’s been a pleasure, but, remember that weird thing I showed you six months ago… well, I’ve decided to leave and launch it as a start-up”.

How did K&E react to your decision to leave and start a tech business?

They were very respectful and supportive of my decision. I think they were also a little concerned that I didn’t jump off into the deep end and make a bad decision.

The senior folks I worked with spent time with me asking me, very kindly, “are you really sure? Talk to me before you hand in your resignation letter.”

It’s quite an unusual path to take for a Big Law lawyer, so I think they wanted to be sure I’d thought it through, and if they could, help me out.

But in the end my mind was made up and they were sad to see me go but understood why I wanted to take a run at launching my own start-up.

Rather flatteringly a few of the partners said, “if I was going to bet on anyone to succeed at launching a legaltech start-up, I’d bet on you”, which was very kind.

And being a little cheeky, I did ask those partners whether they’d personally invest in the company, which they did, and for which I am very grateful!

Had you been thinking about leaving the law before then?

Good question. Leaving the law to start Office & Dragons was part of a broader equation, I think.

For some time, I had not seen myself as a long-term private equity M&A lawyer, or a lawyer in general. I increasingly felt I was being pulled in the direction of doing other non-legal stuff.

As I said, there is this meme that you go to law school and work at a BigLaw firm for a couple of years to pay down your student debt and then go onto your true calling. To some extent that had always resonated with me even though I knew it wasn’t often how people’s plans panned out. But I knew I wanted to do other stuff.

At the same time, I wasn’t certain what that “other stuff” was.

I think this is a common dilemma for lawyers who want to leave the law but are stuck as to what else they’d do instead, especially because you invest a ton of time and money along this long road to becoming a lawyer. It becomes part of your identity. Legal skills and experience can either be, or feel like they are, very niche and not very transferable. Depending on what you do, how you do it and how you present your legal skills, this isn’t necessarily true, but it’s a pervasive mindset. It can be limiting, at least in your mind.

For me, I didn’t know if that “other stuff” was launching a start-up. At the time I really didn’t know much about start-ups. To me they were people in a garage making stuff and eventually, if you are lucky, people give you money and it either succeeds or fails.

I was also mulling over the idea of doing a computer science degree given how much I enjoyed coding and computer science in my spare time. I really do enjoy it and I thought I could be a professor or something.

And then I was also thinking about venture capital, possibly segueing there by becoming a venture capital lawyer.

I should add these thought processes were typical lawyer thinking, excessive de-risking, which I think gets in our way a lot of the time.

My thought process was essentially, “well, before I go and be a startup guy, I guess I should be a startup lawyer because then I’ll learn about startups. And before I launch a tech company, I should probably get a computer science degree… etc.”

What put me on the right track was one of my K&E friends.

He’s direct and says to me:

“Hey Sam, do you actually want to do those things, or do you just think you should do them? Do you have enough money to launch a start-up and survive for six months if that’s what you really want to do?”

And he was right. I started to rationalise the downside. I said to myself and to him, “worst comes to worst and Office & Dragons fails within 6 months, I could get a new job and survive for some time if I keep my expenses in check”.

So he said, “well, why don’t you do just that?”.

That was the nudge I needed.

Was Office & Dragons the idea for your jump into start-ups or one of a few you had in the works?

Not a lot of people know this, but I was torn between Office & Dragons and another idea I was working on in the crypto space.

That idea was a cryptocurrency driven by the value of user generated content. I even wrote a whitepaper about the idea, which I felt was very cool.

But it was Office & Dragons that had gotten the various proof points soonest, and most significantly. That was what tipped me toward Office & Dragons and not my crypto idea.

Before you got to that point, you must have been living a sort of double life: lawyering by day and building out Office & Dragons on the side in your free evenings and weekends? How did you juggle the two?

Office & Dragons was a hobby project for a while, and of course that meant my day job at K&E came first.

However, as a transactional lawyer, work comes in peaks and troughs. It’s feast or famine. Some weeks you work all-nighters and weekends. Other weeks you have very little to do.

Early in my career, the down periods were much needed respite from the busy periods. I would just want to shut off my brain, play PlayStation, watch Netflix, and generally pretend I didn’t exist and that I wasn’t going to be utterly slammed again any time soon.

And for a time that was fine. But then I realised it was avoidant behaviour and, to be honest, not a great use of my downtime when I had all these other ideas on the go.

As such, I started to actively try and turn my attention toward Office & Dragons whenever I got downtime from K&E.

Just on that, K&E does have a certain reputation for being a tough place to work, especially in terms of billable hours and work / life balance. I’m not going to say that it’s not deserved at all, but I will say that I worked with some really wonderful people and overall, it was a very positive thing for my career and a very positive experience, even if it was tough!

For me, the turning point was that I started to realise that I wasn’t fulfilled simply by lawyering. I was finding the time I spent studying coding and computer science around work, often late into the night during evenings and weekends, more invigorating. I started to look for more opportunities to maximise those activities around work.

What sort of resources were you using, or would you recommend to anyone generally interested in computer science or coding?

Too many things probably!

I think it depends if you want to learn coding, or if you want to learn computer science. The two are obviously related, but also quite different.

For me, I started with coding because I wanted to build things and, in particular, learn how to build smart contracts.

To do so I used medium.com a lot. It’s a great resource for explainers and how-to tutorials for a variety of technical topics, but also any topic really. Very quickly when studying Ethereum I got to understand that the language to implement Ehtereum smart contracts, Solidity, is based on a JavaScript type paradigm, so I quickly got into learning JavaScript.

My thinking was that I should learn this older language — JavaScript — which forms the basis of Solidity. One would help me better understand the other.

Also, JavaScript powers the web so it made sense from that point of view, i.e. to better understand the web and how to write internet enabled applications.

On a practical level, given JavaScript is a more established language, it is naturally much better supported in terms of documentation, tutorials, blogs and so on than Solidity, which is much newer and less well supported, albeit the Solidity community is growing all the time.

For JavaScript, I’d recommend Eloquent JavaScript, which is an interactive book filled with coding challenges that you can try to solve, and they have solutions that you can compare yours to theirs.

Another resource that is popular, which I’ve used a little but don’t personally like too much, is www.freecodecamp.com. It’s quite easy at first and is really a long list of small coding exercises. In my opinion it gets repetitive quite quickly, and I don’t personally learn by repetition but instead prefer to learn by building things.

Or more precisely, I learn by failing.

I find the best way to learn coding is to fail at trying to build something. Eventually you go from bashing your head against a wall in frustration to suddenly having this “a-ha” moment where you figure out or find a solution and suddenly things fall into place.

That was what I enjoyed with Eloquent JavaScript. You take a crack at a problem, and even if you get totally stuck and cannot solve the problem, having then seen the answer it’s suddenly much clearer why your solution failed, and you develop a much better intuition and understanding for the next problem.

One word of caution, I’ve since been told — and realised — Eloquent JavaScript is really an intermediate resource vs say FreeCodeCamp, which is more of a beginner resource.

On the computer science side of things, as I said earlier, I was really into philosophy in my younger years, and as such got into logic which obviously has a big role in computer science.

My favourite book by far in this vein is called The Little Schemer.

It’s this question-and-answer style puzzle book. Each page is split in half and there’s questions on one half; answers on the other half.

It’s quite clever. It subtly introduces computer science concepts as an extension of arithmetic and algebra; things that everyone studies in school.

It would be good for lawyers because it’s similar in style to the Socratic method via which most lawyers are taught.

Once you’ve read The Little Schemer, you should read The Structure and Interpretation of Computer Programs or watch the lectures on YouTube.

The YouTube lectures are by the MIT professors who taught what used to be MIT’s intro to computer science course back in the 80s, and this is the textbook they wrote for this course.

Be warned, it’s now considered quite advanced, so not a beginner resource, but well worth the effort to learn if you are really keen! The book really teaches you to think about computer programs and understand how they actually work inside of a machine, which is really fascinating.

Is there anything specific a lawyer or other non-technical person could focus their energies on when learning to code?

Yes, if you learn programming, you could very usefully learn how to build little scripts to automate your everyday work.

More generally, learning computer science or any engineering discipline will teach you how to think about a problem systematically and solve it in a repeatable, efficient, and scalable way. That is hugely valuable because this is totally missing from law school and most legal organisations.

You are not taught how to solve problems at scale. You usually solve a specific problem for a specific client, and are guided by the way clients present you information. You are not really taught how to think about spotting patterns between clients and transactions that can be turned into repeatable, scalable processes, products or services… or at least processes, products and services scalable beyond simply throwing more bodies at the problem, and generally treating all things to all people as 100% bespoke.

Unfortunately, the result is that lawyers tend to overlook opportunities for standardisation, augmentation, or automation of process, which is sometimes because of an “all or nothing” mentality that everything must be automated or it simply isn’t worth the effort.

In most cases, that’s not true. Automating parts of a process can deliver outsize value. But it requires a different mindset.

Any sort of engineering discipline will teach you these missing skills. And that is what got me to think about my own work, more than anything in a different way.

I agree. As someone who learnt to code and picked up pockets of computer science later in life whilst being a lawyer it definitely opens your mind to an entirely different way of thinking.

Sometimes it can be uncomfortable because it challenges a lot about the way lawyers work. This can make those modes of working seem needlessly inefficient, and that’s a deflating realisation. It’s also hard to convince your peers to work and think in that way if they don’t possess the mental models you pick up from engineering disciplines.

Do you think there is a difference between the learning curve for “learning to code”, and being able to get to a point where you can build an end-to-end application? I sometimes think the question of whether lawyers should learn to code conflates this distinction without understanding the difference.

Oh yeah, totally. Learning to code is one thing; learning to build software is another.

Going from zero to building software that works is a long, long journey. Even longer if you are talking about building scalable enterprise grade software with integrations and bulletproof cybersecurity.

It’s not a weekend course, or a few hours a week here and there and hey presto, you have an app that ticks all those boxes.

I distinctly remember learning a ton, feeling great and getting so many ideas flowing. Then I’d sit down, open my favourite IDE (integrated development environment) to start writing code, create my source files, name them something cool and then…

… realise, “where on earth do I go from here?”.

For a long time there it felt like there was a huge gulf between what I knew and what I wanted to do, and needed to know in order to deliver on those ideas.

If you keep plugging away, filling the gaps in your knowledge and going layers and layers deeper, eventually you get closer to something that feels more manageable and actionable.

But you often still get stuck, hit a wall and in that scenario you think it might be better to try and find other people’s code or a tutorial that does something pretty close to what you’re after, and then really get into the weeds of how that works and, crucially, how you can adapt it (or not) to what you’re trying to achieve.

And this is before you even get to good user experience and user interface, which is an entirely separate, albeit related, and significant body of work to master. It looks easy, and we take great UX and UI for granted, but it’s tough to make stuff easy and enjoyable to use.

It’s not just pretty colours!

What you don’t want to do, and what people always do, is make something that only makes sense to them. Understanding what makes good UI and UX great is worth your time.

The elephant in the room before all of that is this: are you solving a problem people care about? Do they care enough about it to pay you to solve it? How can you find this out as cheaply and thoroughly as possible?

To do this you need to get talking to users, understanding what they do, where they do it, how they do it, with whom they do it, why they do it and a whole myriad of often unsaid drivers and context behind all of that. That will give you a lot of clues, and help you build a product that fits a need, or at least improve the probability of that happening. You should then test that product with users early and often to ensure it delivers.

In any one of these areas there are so many layers and it depends how many layers deep you need to get. Sometimes it’s hard to know how deep to go.

As with anything, it’s about taking stock of what you already know, what you don’t yet know that you might need, and weighing that up against what are you willing and able to learn given other constraints like free time and so on.

One of the reasons Office & Dragons didn’t have a UI for a long time was that I simply hadn’t learnt how to build UIs. Most of my programming was back-end and scripting. Books that I mentioned like Eloquent JavaScript are more about functions and algorithms than how to make a UI with buttons.

Because of that, I started to read about things like event handling and UI systems. At the time, I decided these were really complicated and that I’d park that area until it felt necessary, instead preferring to build a command line tool initially to test my idea because that was what I was comfortable doing with the knowledge I had.

Of course, I had to learn a ton of other stuff along the way, such as manipulating Microsoft Office files and file system storage.

It’s an iterative kind of process: eventually you hit the point where you realise, okay, there’s some functionality here, but there’s no escaping that no-one’s going to use it as a command line thing — I need a UI.

At that point, I knew enough to make the app achieve what I needed it to achieve and couldn’t really learn much more to take things forward, except to then skill up on UIs and build one for the app.

At any point did you start thinking about bringing others into the process, e.g. to help with the front-end or similar that sat outside your core expertise?

Yes, I did start to think about when that point would come. If you’re doing everything yourself, as I was, because it’s your project, after a while, things can balloon. You figure, “maybe I need a hand”, at least to divide and conquer the tasks more quickly without also having to learn how to do the tasks on the fly.

I think delegating and teamwork is hard for lawyers. This is a controversial opinion, but I don’t think we as lawyers work in teams. Or not in the sense of teamwork understood and practiced outside of law.

I see teams in non-legal organisations like a pack of dogs, everyone is pulling in the same direction and being led toward a goal and sharing in the spoils.

Lawyers are maybe more like a team of cats. We are solitary and proud, and I think barring exceptional circumstances we always try to solve problems ourselves before leaning on others for help.

It seems to work fine for legal organisations, but it isn’t how to run a company. Of course I can play nice with others, be a team player. Of course I can do that.

It’s more a weird pride thing, I think. An acceptance that there are things I don’t know how to do, that I’m not going to learn to do, and that I’m not going to be good at doing them, and instead, I am going to rely on other experts to do those things for me and entrust their skill and knowledge to that task.

I think this is a hurdle for lawyers to overcome when switching into a business role, or leading a company, and perhaps all the more if that company is also your pride and joy.

But getting over that is great. We’ve built a fantastic team at Office & Dragons, all of whom are way more skilled and knowledgeable about the stuff they do than I am, or I’m ever going to be.

I will say my job as the CEO at an early stage startup is to usually do everything for the first time, usually because we don’t have a person for that thing. I do that thing for the first time, figure out if we need it, how hard it was, and how we might find someone expert in it to do it better than me and take it from there to something really great.

How has your legal career, helped or not with starting and running Office & Dragons?

Not to be pessimistic, but… there are certainly ways it has not helped, which definitely stand out in my mind because they were really big struggles, and to be honest, also surprises!

I tend to find that the things that help you aren’t as noticeable as the things that stand in your way.

For instance, lawyer skills focus you on the minutiae and spotting differences where other people can’t find any and wanting to be 100% sure about this or that. These skills don’t lend themselves to start-ups.

As my earlier story about spending the better part of my gap year in the Congo evokes, I wasn’t a risk averse person prior to becoming a lawyer. In fact that was probably the opposite! I was pretty risk-seeking.

I loved to play poker. Absolutely loved it. One thing that happened to me when I started my legal career, maybe as soon as one year into it, I became horrible at poker and I did not enjoy it at all anymore because of the ingrained risk aversion I’d developed through lawyering.

It got to the point where I would not want to play any hands because I just couldn’t do it without certainty of victory. I couldn’t bluff because I just didn’t want to play those hands full stop. I wanted the certainty that I would win, which with a bluff you necessarily don’t have. It’s never certain.

As a lawyer, if your client says, “should we do X or Y?”, you need to be as precise as you can be and say:

“If you do X there’s an 80% chance of this and a 20% chance of that. Or you can do Y, but we don’t recommend you do Y because although 95% of the time the result is fine, 5% of the time it’s bad and might result in some big sum of taxes or similar.”

It’s hard switching gears, and I say that as someone who was a risk taker and became much less so the more lawyering I did. Some lawyers are naturally risk averse. That’s why they entered the profession, but that wasn’t me, I was a risk taker and I still find it hard turning down my trained risk aversion.

When you’re running a start-up you’re faced with making many decisions. As a lawyer it’s easy to fall into the trap of analysis paralysis.

I did this a lot at the start.

I literally spent days deliberating over where to incorporate Office & Dragons, whether in the UK or the USA. I tried to research the tax law in various jurisdictions. I tried to talk to specialists. I tried to map out my possibilities for tax gains and losses in different setups. It was a huge rabbit hole that stopped me making real progress. I was telling people who wanted to invest “sorry, I need to finalize the incorporation and tax structure”.

That’s just one example, but this would happen repeatedly with every decision or enquiry, no matter how unimportant it was in the grand scheme of things.

Anyways, many months of being like this went by. I became more and more frustrated, exasperated to be honest, and just decided that I need to make decisions with imperfect information and live with it if I wanted to make a go of running a start-up.

Have you managed to improve?

Yes, I’ve gotten a lot better at this, partly through experience and just doing it. I don’t find myself sweating those things anymore.

The challenge is that as a lawyer you don’t get to make decisions one way or another, at least not in the substantive sense of this will make or break something. More often you are advising a client on the matrix of decisions they wish to make and will make, not your own decisions, if that makes sense.

On the positive side, I will say that being a lawyer makes you build confidence at presenting, speaking and generally asserting an opinion with conviction that is hopefully persuasive.

That’s very important, whether you’re raising funding or you’re talking to a prospective customer. You need to win them over and present a clear value proposition, often quickly.

It’s all the more important because when you’re starting you have to back yourself. You’re just this one person and you made this thing and aren’t yet maybe a real company so you’re absolutely going to have imposter syndrome. You’ve got no track record. You’ve never done this before. Who are you to know or say anything? Why should anyone return your email, call or listen?

These are the scripts that can play in your mind.

It’s difficult to work around these generally. It does get easier I think, and I think is made easier if you have been a lawyer of some sort, particularly perhaps a litigator where there is even greater emphasis on communication.

On communication, another lawyer habit I’ve had trouble shaking is the time I spend on emails. As a lawyer you are hyper vigilant about what you do and don’t say in email and how you say it and who is copied etc because getting that wrong can have disastrous consequences for you, your client, the firm and so on. I still disproportionately agonize over emails, knowing full well I should be more proportionate in how I spend my focus. I’m making a conscious effort to improve this!

What do you think has been the most surprising and least surprising since you flipped over from being a corporate lawyer to running a startup?

I work way more than I did as a lawyer, which I totally did not expect.

Believe it or not, doing cross border Luxembourg-domiciled private equity transactions translates 0% to trying to figure out your own startup legal documents. As it turns out, the standard UK startup seed investment documents are alien to me. I would look for my Luxembourg topco and just not see it!

So yup, that was surprising, that I need to do all these legal things I thought that I could do on my own, yet in fact couldn’t do. I simply didn’t have the experience: despite being a corporate lawyer. It’s surprising how niche you become as a lawyer even very early into your career and how much legal stuff you don’t know.

Least surprising is that running a start-up is extremely satisfying.

I was always unsatisfied as a lawyer, and I hoped that launching a start-up — being the principal in a commercial situation not the advisor — would scratch that itch, and plug that need, which it has.

That said, it’s definitely a lot harder than being a lawyer. Obviously, the pay is way worse, that’s for sure, and hopefully that improves. But right now, I wouldn’t want to do anything else. I really like it: the dynamism, the decision-making, building a team. All that good stuff.

For anyone interested in working in legaltech or similar, what skills and experiences do you think that they should be seeking to acquire, how they might find them, where they might find them with who they might need to connect?

That’s a broad question and it’s probably hard to give a concrete or satisfying answer. I’ll do my best but open with the classic legal response: “it depends.”

Concretely, it depends on what you’d like to do within legaltech.

You did this really great article on this point, about non-legal tech, the idea of fully exploring general tech and its application to legal business problems.

That goes to my ethos, that legal as a field, and legaltech as just another flavour of tech, and lawyers as knowledge workers are, in each case, not very special categories — no offence!

A legaltech company isn’t very different from a tech company. Legaltech software isn’t very different from general software.

The challenges faced by the legal profession are no different from those affecting banking, accounting, or any other knowledge discipline. To be honest, they’re not necessarily that different from stuff in marketing or HR, which to most lawyers would seem a silly comparison to make, but it’s true in my opinion.

Take away the domain and a lot of the jobs to be done are pretty similar when you get back to first principles.

This is pivotal when thinking about software as a solution to those challenges. It’s all the same broadly speaking.

In terms of how this understanding might help people, I’d say it should encourage you to look beyond legaltech resources.

If you limit your knowledge about tech to only legaltech, you’re missing out on a lot of really good stuff and often more mature thinking elsewhere, or simply missing out on other people’s solutions to more or less identical problems, which might save you reinventing the wheel as, your article pointed out.

I’d also say read around tech topics.

A specific example might be learning about the means for process improvement, the tools and frameworks etc. This stuff is well trod outside of legal and only quite recently seeing wider application in legal. Instead of focusing on legal specific resources, Google process improvement generally and find case studies, explanations, and examples from outside of legal. The same goes for product management and design. If you can find a non-legal resource it will likely be more in-depth and time tested, and may highlight how to do something you need to solve and save you reinventing the wheel by shoehorning these ideas into legal ways of thinking.

That said, there are upsides to getting this sort of information from legaltech or legal specific examples. These nuggets however will be centred around challenges specific to legal, particularly some of the esoteric adoption challenges faced by law such as the billable hour model that butt up against the typical time savings and efficiency effects of good tech sat atop some refined people and process. All that to say, this — billable hours and adoption etc — are still really about incentives and how they enable or inhibit behaviour change, which is a time tested and well researched topic applied to a huge extent outside of legal!

What advice would you give to individuals wanting to start a company of their own, whether it’s a legaltech company or any startup business?

Test the market. Do what I did relatively little of and talk to a lot more people than I did. I did a lot, but not enough in hindsight.

There’s tons of resources on how to have those conversations. Your objective is to figure out what it is that you can deliver that people want and will pay for.

I think you also need to decide what type of business you want to build and why.

For some folks they want to build a lifestyle business, i.e. one that supports their lifestyle or a particular lifestyle and aren’t too fussed about simply seeing how big they can grow it. What you need there is a relatively high certainty of guaranteed income, or at least a relatively certain and near-term road to getting there.

If you want to go after a ton of VC money and do the cliché “change the world” type venture, that is something else entirely. Going down that road requires a market size in the billions and those are difficult things to find, to prove and to build.

Be very critical with yourself as well. Not in a pessimistic way, but in a realistic and constructive way. Most people aren’t, especially I think when they’re building in their own domain.

When building for your own domain the two biggest traps are these:

One, that you overestimate the size of and value of the problem. Just because you had it, and it really sucked, doesn’t mean it sucked for everyone or perhaps didn’t suck as much for everyone as it did for you. You need to find out how much the problem sucks for everyone, and how much value they place on it being solved by you.

Two, and tied to the above, how much are people willing to change their behaviour in order to solve the problem even if it really sucks. For instance, if you are trying to get a bunch of banks to work together and totally change their way of working, that is going to be tough whether or not the problem is one they all hate and would love to solve. The ease (or not) of changing behaviour needs to be outweighed by the value of solving that problem, often quite significantly so.

If you can solve a problem that is really painful and solve it with as little friction or behavioural change as possible then you are onto a winner. This is why Google search dominated. It was easy and 10x better than incumbents. Switching was a no brainer.

Another issue is trying to average out the requirements for the product. It’s very easy to build something that, as the user, I would like and understand very easily, e.g. that the button looks like this and sits over there and is this colour and has that label. The easiest way to break the assumption that your design decision makes sense to all users is to go and ask two users what they think.

Inevitably you will find that both have different opinions from each other, and they’re both different from yours.

You need to have these conversations, and keep having them otherwise you will build the wrong thing or solve the right problem in the wrong way, which is perhaps worse than building the wrong thing or solving the wrong problem.

What do you know now that you wished you knew earlier in your career?

Do the thing you want to do, do it earlier, be a little less safe, and don’t necessarily spend as much time building up to it or putting obstacles in your own way.

As I said earlier, don’t feel that “before I do this I have to do this other thing and this other thing and so on” feeling.

Ask yourself whether that’s really true, just a delaying tactic, or excessive de-risking. If you don’t, you may never get to where you truly want to be and take the chances you desire.

Take more risks. Don’t be reckless, but take some risks.

Don’t catastrophise about what if it doesn’t work out. Often, even if it doesn’t, you gain skills that lead to other things.

Tunji William’s career journey featured in one of your earlier profiles is really awesome.

He’s a good example of someone who took his lawyer skills, took some risks and put it all on the line running a tech start-up, which unfortunately didn’t work out, but after went on to work at Litera — a really large tech company — leading ways to attract, grow and maintain their customers and has folded these skills and experiences into his new role leading a really cool and different social enterprise.

You’ll land on your feet most of the time. It’s like they say, shoot for the moon, cause even if you miss you’ll land among the stars!

Wrapping up, do you recommend any books, podcasts or other media relevant to legaltech, startups, careers, anything that you’ve found influential for your career to date?

I definitely recommend Lawtomated. I think it’s a very legitimate resource, especially for folks that like the techier side. I like how you’re willing to take the extra step and lay out the techie side whilst striking a good balance. I don’t feel I’d be turned off or unable to follow if I didn’t have a technical background, but equally I get something extra from it because I do have that knowledge.

I will say that Nathan Corr at the University of Aberdeen is doing a fantastic job with their legaltech society. They put on some great events, real quality stuff.

Thinking again of students in mind, there is a blog called the Exploratory Journey by Ved Nathwani that has blossomed into something awesome. And I am not saying that because he also interviewed me! Ved has gone on to interview way more interesting people than me.

I do think that what Ved’s project teaches is the importance of network and not being afraid to put yourself out there. Ved is a high school student and is using LinkedIn to reach out to people and I’d imagine not everyone he messages responds or gives an interview, but over time, with enough tenacity you can — as he is doing — build something and in doing so, share some great knowledge.

I would also say that I often have people reach out to me on social, and I love helping out and giving advice where I can. So please feel free to reach out to me on LinkedIn or Twitter. I say that whether you are a law student, a non-law student, a lawyer or non-lawyer considering a career change or starting a business. I’d love to make myself a resource to you and help in any way I can!

In terms of books, and other blogs, I really like:

• Reforge. This is an amazing blog stuffed full of resources on growth hacking and many other cool business ideas. In particular there is this great article by Rahul Vohra, founder and CEO of Superhuman, an email productivity app that has grown like crazy. That article is about ways to measure product market-fit, using leading indicators and other techniques that they seem to have honed.
• First Round Review. This is a blog by the VC fund, First Round. They put out a blog that covers some excellent founders sharing practical and actionable knowledge for anyone in start-ups.
• Patrick McKenzie, who works at Stripe Atlas, has written a wealth of excellent material on SaaS pricing. This is a particularly detailed guide and well worth your time if you are interested in how to price SaaS. See also here for his essays.
• Aaron Dinnin who writes on medium.com and teaches entrepreneurship at Duke University. He’s a super nice guy. I reached out to him after reading his content and he was kind enough to meet. He writes about a lot of entrepreneurship ideas that I’ve not seen elsewhere.
• Saastr has a wealth of resources about SaaS businesses, how to build and run them. Jason Lemkin, who runs it, also shares lots of interesting observations about the SaaS market that get a good conversation going on twitter. Well worth a follow if you are keen on SaaS.
• Forentrepreneurs.com by David Skok has some amazing resources on unit economics, and how this breaks down. It’s a difficult topic, but one you have to understand when starting and running a business. His guidance — e.g. this article — on that subject is second to none from what I’ve read so far. The biggest problem for a lot of start-ups is that they don’t know their unit economics. His blog is a good way to understand these and be able to explain them to investors — very important!

⚡ Interested in legaltech careers like Sam’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

Devshi Mehrotra is a 2021 Forbes 30 under 30 lister, and co-founder of JusticeText, a start-up using artificial intelligence to transcribe and analyse audio-visual evidence, including bodycam footage, interrogation videos, and more. By doing so, Devshi is helping public defenders be more productive and effective in their jobs, who serve a crucial role in the criminal justice system.

And Devshi is only just getting started!

Graduating in 2020, Devshi has been busy for several years, gradually combining her passions for computer science and criminal justice reform alongside her studies, and ultimately building a start-up that harnesses both.

In this interview we explore how combining computer scientists with lawyers can unlock new value and widen access to justice. We also discuss the landscape for women in tech and ideas on how the tech community and educational systems can do more to widen access and drive engagement across under-represented groups.

Unlike our career profiles to date, featuring individuals a decade or more into their careers, you are just getting started. But you’ve already done an incredible amount of exciting things. Can you walk us through your journey to date?

I’m a recent graduate. For my undergrad I studied at the University of Chicago, obtaining both my bachelor’s and master’s in computer science there.

After attending the University of Chicago I spent a year at Tsinghua University in China, where I received a masters in Global Affairs.

How was studying in China?

It was really exciting, albeit a little disrupted by the outbreak of COVID-19 whilst I was there!

The program was very different to my previous computer science studies, but it was incredibly eye-opening in terms of content, teaching and the variety of students from all over the world, including from India, Pakistan, Southeast Asia and all across Africa.

I really loved living and studying in China. I think many Americans still internalize this idea that the start-of-the-art is what is produced within our borders… but going to China, there is no question in my mind — China is so far ahead in many areas, whether its developments in public infrastructure, smart cities, transportation systems, and generally integrated approaches to managing a lot of urban challenges. In those areas, China is really pushing ahead hard and fast as compared to the USA.

I should add that I studied Chinese for four or five years before studying abroad in China, and so it was also a culture in which I had personally invested a lot of time and energy getting to know. So from that perspective, it was great to immerse myself in the culture first hand.

And between your various studies you’ve managed to cram in a lot of exciting internships. Can you tell us some more about those experiences?

Yes, alongside my studies I completed internships at several big tech companies, predominantly in their machine learning research groups.

In my first summer I interned for Facebook, collaborating with two fellow interns to build Reach, a mobile platform designed to connect volunteers with service opportunities in their community. As part of that internship I personally presented our project to Mark Zuckerberg as recognition for having built the Best iOS Application in the Facebook University program.

Into my next summer I got to work at Google Brain, working on a variety of machine learning and robotics projects. That internship got me really excited about the world of AI research and led me to spend time in London at DeepMind.

You are also very passionate about social justice reform, a very different domain to computer science, albeit one that impacts everyone. How did this interest develop?

While my undergrad major was highly technical, I also spent a lot of time in the city of Chicago, getting involved with local organizing efforts around criminal justice reform.

Unsurprisingly given the events of 2020, the national conversation about criminal justice reform has really exploded over the last year.

But in many urban communities, criminal justice reform has been an on-going conversation for decades. Policing and community relations are often fraught because of America’s long history of racial discrimination.

So on the one hand I was spending a lot of time involved in these really incredible activism efforts, but on the other hand, spending summers working in high tech environments and communities. Two very different worlds.

The juxtaposition of these two experiences lingered with me for some time. In particular, the disparity of resources between the two environments stayed with me. It also made me realise that what I really find purposeful and meaningful was engaging in direct action.

And is this why you started JusticeText?

Yes, JusticeText is how I’ve melded my interests in justice reform and my skillset as a technologist.

I should say however, that initially I had no idea what that was going to look like, but one day I just decided, “you know what, I’m going to show up at my local public defender’s office, start a conversation with them and see where I can take it.”

And that’s how JusticeText got started. It started just before going to China, while I was still an undergrad in Chicago. It began as a school side project, just something that me and Leslie Jones-Dove, my co-founder, whom I’ve known since our first day as freshmen, were working on.

We built a rather bare bones prototype, but it was a start!

After that we began outreach to different attorneys, agencies and so on. I continued this alongside Leslie whilst I was in China, often meaning I was having to jump on calls at 11:30pm local time in China to do product research, interviews, set-up trials and move pilots forward with existing and potential users. During that time Leslie took on a lot of development work.

I actually didn’t expect to commit to building JusticeText full time until after graduating, but I am so glad I made that decision.

Can you tell us some more about JusticeText?

A major problem public defenders face is high volumes of data. This problem is only getting bigger. Whenever an event happens that has some police, legal or other implication there is a ton of data created via, and collected by, the US justice system, from body camera footage, interrogation audiovisual data, transcripts, jail phone calls, witness footage from smart devices and so on.

This is perhaps not all that surprising when you think about modern life and how much technology permeates everything we do.

The surprising part however is that there is very little to no infrastructure in place for public defenders to make sense of this information quickly, effectively and thoroughly. Instead, many public defender attorneys themselves or with the help of others have to manually transcribe, organise and sift through hours and hours of data, in particular an increasing body of audiovisual data, trying to synthesize information and understand the full facts of a case in order to ensure justice, and access to it.

Layered onto that, these public defenders have huge caseloads: 200 maybe 300 cases at any given time.

Even the best attorney will struggle with this heavy workload and voluminous data. The risk is that something gets missed, evidence perhaps that could in fact be decisive to a case, whether advantageous or harmful to a client. There’s a lot at stake.

As technologists, we saw inefficiencies that were contributing to injustice. We felt technology solutions could help solve some of these problems.

So the tool itself, JusticeText, is a web platform. Public defenders upload their discovery data directly to the system.

Attorneys can then quickly confirm things such as the primary language spoken, tag by evidence type, add metadata as is relevant.

Any audiovisual data is also transcribed so that every single word has a time stamp. And so you can click on that word, and jump to that part of the video. We have also started doing some preliminary keyword extraction of terms that might be relevant to legal analysis.

That’s very cool. With regard to natural language processing in this context, is it possible to apply something like sentiment analysis to provide leading indicators for attorneys, e.g. highlighting potentially hostile language, or vice versa?

That’s one of the areas where we would love to move forward! One of the things that I’ve noticed is that sometimes it’s as much the intonation of the voice as it is the raw transcription that indicates whether or not someone was angry or upset.

And so the experiments we’ve run have been inconclusive in the sense the insights we can provide are interesting and clever, but perhaps not the most useful. At least not yet!

It’s an area with which we will keep experimenting, and we’ve explored numerous off the shelf tools in that regard as well. There’s undoubtedly lots of ways we can gradually increase the sophistication of the technology beyond the automation of searchable, tagged and taggable transcripts.

Just to back up for a moment, you mentioned an initial idea before the current JusticeText concept — what happened with that idea?

Of course, the first idea already existed as we discovered quite quickly.

As a result, we flipped the conversation, explained our background, the skillset that we bring and asked open questions, “are there any things that you’ve been struggling with that you think could be helpful if solved?”.

The interesting thing about being a technologist in the legal space is that you don’t bring domain expertise, so the number one thing that you can do, is bring empathy and a willingness to listen and to learn about problems. You can also help by looking at problems in a different way to those deep in a particular domain.

It’s worth saying that I was not tied to our original idea at all. It was a starting point for a larger discovery process. If several people are telling me that something else provides value, then we might as well focus our time and attention on solving that problem. If they are saying the opposite then it’s a sign there are better problems to identify and solve.

That’s a great point. I agree that outsiders often breathe fresh ideas into other domains. If you come to domain A from domain B, you aren’t path dependent or predisposed to accept the status quo but more likely to question why something is a certain way. That can be really hard to do if you’re deep inside your own domain.

So how did you take things forward from these initial problem identification discussions?

We’ve been in product development mode for the past year, and after I graduated in June of last year, I gave myself two months to try and raise the initial funding for JusticeText.

My thinking was this: if I can succeed at some initial fundraising, then I’ll commit full-time. And thankfully we raised a pre-seed round of around $300,000.

That fundraising has helped us add two additional engineers — it’s made a world of a difference for us.

Our extensive efforts running user interviews, feedback sessions, surveys, and so on is paying off. We’ve moved on from scoring 3s to 6s out of 10 to consistently scoring 9s and 10s out of 10. It’s a long process, it’s not easy, but totally worth it! And we’re still only in the very early iterations of the product, so the long term view is very promising.

Now we’re hitting our stride in terms of product, my aim is to shift from day-to-day product management into launch readiness. We are hoping to officially launch in summer of 2021. So far we’ve had very encouraging conversations with various states and counties with regard to winning government contracts so that our platform ends up in the hands of more public defenders.

What was it that improved the user feedback scores? Was it new features, or a reframing of existing value?

There’s a couple of things.

One is the messaging. Initially, attorneys struggled to see the big picture, the problem we were trying to solve. When they heard terms like “transcript” and “transcribe” they tended to see it as simply transcription, which they already do, albeit very slowly. Framed that way, they couldn’t differentiate the value vs. the status quo.

But in reality, the value isn’t just the transcription technology, but the workflow we create around that technology. That workflow is JusticeText’s real value: making it easy not only to transcribe, but also to review, edit, tag, collaborate around, and generally leverage transcription data in ways that make sense to attorneys. We’ve managed to improve product and the user experience, and the surrounding messaging, so that this value is more immediately obvious to users.

The other thing is the accuracy question.

Like most machine learning tools, it’s not always terminal that the system isn’t 100% accurate. Initially early users used to say “hey, it’s only 75% or 80% accurate, I can’t use this etc”. So we had to do a little reframing to help users understand they needn’t take an all or nothing approach — even less than 100% accuracy is still a massive time save and value add vs. the status quo processes, especially when you layer on the workflow features.

Cognisant of this feedback, we’ve been more intentional about addressing those issues in the last couple of months, which has made a big difference.

That’s a really interesting observation regarding AI accuracy. We’ve seen a lot of AI tools fail, or underwhelm, not because of accuracy but because of poor or entirely absent workflow tools. Attorneys tend to get overly focused on accuracy, because in their mind it speaks to risk, which is what they know. What they are sometimes less good at is understanding how other factors have outsize impact, in particular the power of good workflows when paired with “accurate enough” AI. There’s a reason other knowledge based or highly skilled industries — such as surgeons, pilots and astronauts — obsess over workflows, but lawyers don’t always appreciate their power.

On this point, do you think having a computer science background helps you see these sorts of legal challenges differently?

The time that I’ve spent with the Silicon Valley community has been very influential. They are laser focused on workflow tools, even for what seem like the tiniest things.

VC funds are similar. They seem to try and automate as much as they can, whether that’s reviewing emails, pitches and organising calendars etc.

The individuals and teams in those spaces just seem to have this immediate urge to innovate problems away, especially anything remotely capable of being turned into a workflow of some kind. And everyone in that space is super interested in what tools and methodologies each other are using to be productive. It’s embedded within that environment; it’s the norm not the exception.

This background definitely helps me see opportunities for better workflows when I meet with attorneys to discuss their pain points and what they do. There is a huge opportunity to improve things, and a growing number of young technologists who are keen to help innovate this sector because they want to make a difference.

Have you seen openness to, and enthusiasm for, this type of thinking when working with lawyers?

It depends. Without wanting to generalize, the incoming generation of public defenders seem more open to these ideas and ways of working. They’ve been the easiest adopters so far. Perhaps that is because they are as yet less ingrained and path dependent on the traditional ways of working.

But I do think, in part at least, this incoming generation of lawyers have different expectations because when they’re dealing with their finances or social media or transportation, they expect a high-quality user experience. I think the lack of these sorts of experiences in legal processes is probably at odds with those expectations, which is perhaps a good thing and will encourage the incoming generations to be change agents and prioritise workflows to aid their own work and enhance client service.

You’re right — there’s definitely a widening gulf between how consumers experience tech and how they experience tech in legal products and services. There’s not too many good reasons why this gap persists!

Thinking again about you as a founder, can you walk us through your interest in start-ups, and what tips you would suggest for starting a business?

I went through my phase as a college student where I just wanted to start a business for the sake of starting a business. But I quickly realized that the only things worth pursuing as an entrepreneur were causes I was genuinely passionate about.

In fact, JusticeText absolutely didn’t arise from these earlier interests in start-ups.

Quite the opposite. Rather, JusticeText was sprung from my interest in justice reform, which became a bit of an obsession. I couldn’t stop thinking about the underlying issues, day in, day out. I was taking classes, attending lectures and just trying to learn as much as I could. I would say to any student entrepreneur, or any entrepreneur generally, to look for issues and problems that you and others really care about solving. College is such an incredible environment from which to explore these challenges and opportunities. You are surrounded by so many brilliant minds and have such incredible access to them.

I’d also say that being a student opens a surprising number of doors. People tend to give you the benefit of the doubt and want to help you because you’re a student. That means there’s a world of opportunities to seek out interesting people and problems.

If as a student, you can leverage these opportunities once you find that problem that you can’t get out of your mind, that you’re thinking of day in and day out, you’re probably onto something. It might not be the thing, but it is more likely to be a goer than setting out with the vapid objective of just starting a startup for the sake of it. At the very least, it will be the starting point for a productive set of discussions that may lead to new insights you can action and solve via a start-up business idea.

So don’t sit in your dorm room worrying about market mapping everything and coming up with your financial models in a vacuum. Get out there! Literally go to the community that you care about where the problem is experienced the most. Be curious, ask questions. Do work for free in the beginning. Volunteer your talents and experience. Exchange experiences — help someone, and they will help you.

That might mean helping someone solve a part of the problem, who later becomes an early adopter and champion of your mission. If you can find individuals who are frustrated by the issues you’re seeking to solve, they will give you a lot of time. People like to talk about themselves and share their problems, especially if they think you can help solve them, and if you are genuinely interested in solving them.

That’s your first pilot user, and perhaps a first customer.

Once you lock in those initial interactions, lean into those relationships. Really invest in them. We did this for six months, getting immersed in the users, their jobs to be done and their pain points and the wider structures of government and government technology. I’m more a govtech expert than a legaltech expert as a result.

As a result, we got to know a lot of the systemic barriers of government processes, including procurement and so on.

To find these interactions, you have to be proactive: shoot your shot.

Sure a pre-existing network helps, but don’t think that you need one to do this type of work, or that if you don’t have one you can’t start.

As long as you’re genuine and authentic about the issues and the people, you will easily build your own network.

That’s really good advice. Thank you for sharing. It’s great to see you and Leslie diving straight in, meeting with real users and really getting to know the pain points and other structural drivers behind the status quo.

Changing directions, I know you’re passionate about widening access to computer science, in particular your CompileHer initiative — great name by the way — to build role models and encourage women into tech. Do you mind sharing your thoughts on this subject?

In the USA, one of the interesting things that you’ll notice, is that a lot of the women in tech come from immigrant families.

For whatever reason, we tend to come from a family background that really encourages and supports young girls. Now that sometimes means there are unreasonably high expectations placed on young women, especially when it comes to succeeding in STEM subjects like maths and science etc.

Ever since I was little, that expectation was built in, that I would pursue STEM interests and that they were objectively valuable skills to hone.

But it wasn’t an expectation I saw shared in any of the TV or other media I or my friends encountered. It was an expectation stemming from my parents.

What I thought was normal — prioritisation of STEM excellence and similar — I soon realised wasn’t the experience of many others.

Many women don’t have parents or families with that inbuilt understanding of what it means, and what is required, to succeed in STEM subjects or how rewarding those subjects can be in every sense. There aren’t any STEM heroes, or glamourized individuals aimed at young girls. There’s plenty of male role models, but few females.

I wanted to change that. I just knew I had to do something. And CompileHer was one of my biggest passions in college. It’s an organisation I led an undergraduate, spending hours every week educating young girls about computer science and engineering, role models and just trying to get girls aware of, and enthusiastic about, STEM subjects.

I really wanted to plug the gap between different communities.

I wanted to do everything I could to ensure that the girls in my school have every single opportunity that any other student might have.

It was fantastic building these relationships as a college student with teachers, principals, parents and young girls. Occasionally I hear stories of how some of the girls have gone on to pursue interests in STEM subjects, which is really meaningful to me!

In terms of what we did, we organized hackathons, conferences, workshops and things like that.

That message I conveyed wasn’t so much simply “everyone should learn computer science” but more specifically “you should learn computer science because there’s challenges that you uniquely understand via your lived experiences, that aren’t shared by everyone and without you those challenges won’t get solved”.

What do you think the best way is to encourage more women into tech? Do you think it’s these grassroots, early interventions to build awareness that these opportunities exist and that women have unique experiences they can bring to a traditionally male dominant domain?

It does help. In some cities across the US, school districts are actually mandating computer science education as a high school graduation requirement. So there is now this system wide change being enacted that is going to make a world of difference, it’s called Computer Science for All. They also have specific focus on getting under represented groups into tech.

It’s fantastic, and the result of numerous incredible people devoting years and years towards building curriculum and advocating for change.

So that’s one part of the equation — making computer science a pillar of education generally.

The other part is tackling the fact that the majority of folk in tech aren’t women. This can be incredibly discouraging as a woman if you look around and there’s very few women in general and in senior roles. And I felt that way many times.

In tech mentorship is also an issue. In tech you are encouraged to try things, crash and burn and hopefully learn from the results. But for a lot of women, they feel hesitant to crash and burn before learning all of these things first. Creating environments where women engineers can come together, e.g. young girls who are trying to get into the space, can make a huge difference as well.

Do you have any books, podcasts or other media you’ve found influential with regard to what we’ve discussed?

Yes, a major reason for starting JusticeText was because of The New Jim Crow by Michelle Alexander. This book is now a very well known book. Professor Alexander is a lawyer and activist and her book explores the systemic biases of the American criminal justice system and how it functions as a contemporary system of racial control, relegating millions to a permanent second-class status even as it formally adheres to the principle of color blindness. A lot of the time when people think about racism, they think it’s limited to discriminatory comments or actions that are overt, or individual bad actors making bad decisions. This book takes a systems level approach, which tells a different story of the many hidden — but powerful — structures that contribute to racial injustice and require reform.

⚡ Interested in legaltech careers like Devshi’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

What could a career in legaltech look like? What skills and activities are required and undertaken in legaltech, legal ops and legal innovation roles?

In this part 4 to our 6 part careers guide we will summarize a representative, but in-exhaustive, list of typical legaltech, legal ops and innovation skills and activities.

In part 5 we will explain specific roles that embody these skills and activities.

By the end of this part 4 you should have an understanding of what people in those legaltech, legal ops and innovation roles actually do, and by reading part 5 you will understand how they apply to specific roles!

Let’s dive in!

A caveat

As with any categorisation effort, some generalisation is necessary. A lot of the roles in legaltech, operations and innovation overlap even if their titles are different, and equally can vary where their titles are the same or similar. Teams in this space remain relatively small, so a lot also depends on the individuals.

Please bear all of this in mind when reading the below, and also part 5 where we describe popular roles.

Notwithstanding these caveats, the below and part 5 provide a roadmap to the most common skills, activities and common roles.

Organisations

The skills and activities we describe below are common to different types of organisations with legaltech, legal ops or innovation teams or roles, including the below:

• Law firms
• In-house legal teams
• Vendors
• Consultancies

01. Research

The ability to gather information about a topic, review that information and analyze, interpret and present the information in a manner that helps reach a decision or solve a problem.

Research problems and questions in legaltech might include:

• Competitive analysis, e.g. what are my competitors doing and why?
• Process analysis, e.g. how does this process happen and how can it be improved?
• Vendor comparison and selection, e.g. what document review vendors exist? How to select them? How will we measure success? Who uses them? Do we need them?
• User experience and acceptance, e.g. how do users experience our product? What bugs or blockers did they encounter? What features are we missing?

02. Scoping

Scoping is about the identification, qualification, quantification and prioritisation of opportunities for innovation or problem solving generally.

Scoping may also be useful in a sales cycle (see part 5 regarding sales roles) to qualify whether or not a prospective customer is a fit for your product or service. If so, great; if not, you need to bow out of the relationship to avoid mismanaged expectations and potential reputational damage (and to save you time and resource).

Scoping is often undertaken by interviewing and / or surveying stakeholders to understand the product or service in solution to a problem that is to be created, improved or bought, including the business case for taking action.

Sometimes these interactions may be run as a focused workshop, aimed at delivering a collaborative exploration of a problem, together with ideas for its solution. In other scenarios, this may be a more casual conversation, e.g. in a sales context to find out whether a prospective customer’s problem fits your product, and whether they are ready to buy (e.g. do they have a business case signed off? Are they the decision-maker? Etc).

Whatever the means, the aim is to understand, what is X, how does X happen, why does X happen, who is involved with X, when and where does X transpire? Can X be solved and is X worth solving? If X only affects 1 person and marginally so, it may not be worth solving X, or certainly suggests X has a lower priority than Y which impacts a larger number of stakeholders, or a similar number of higher value stakeholders.

X in this scenario is the user’s problem, or need. If you don’t ask these questions you won’t understand X and may end up trying to solve the wrong problem, or worse, the right problem with the wrong solution.

Scoping is also critical to ensure that what you agree to provide aligns with what the receiving party expected and ultimately receives.

Scoping is therefore necessary to define and agree the expectations on both sides.

• In a sales context, this might be the specific products, services or configurations of those items that the customer intends to buy.
• In a process improvement context, it might be the number and type of processes to be examined and improved.
• In a product scenario, it might be the ambit of features or use cases to be tackled in a particular sprint or roadmap epoch.

Scoping can also be useful to divide and conquer problems.

For instance, you can map out the entirety of a problem or set of interrelated problems, and then break these into chunks or phases, making it easier and more manageable to tackle. You can also add breaks between phases, e.g. if phase 1 is to test the viability of a solution to a problem, and it fails, then phase 2+ may fall away. If you had simply agreed to deliver everything, without agreeing to test the viability of an initial solution at the end of phase 1, you might waste considerable resources ploughing through later phases only to realise the solution is a flop.

If you don’t define and agree on scope, the result is usually differing views as to what was in or out of scope, resulting in scope creep.

Scope creep is the continuous or uncontrolled growth in a project’s scope, at any point after the project begins. This can occur when the scope of a project is not properly defined, documented, or controlled. It is generally considered harmful! Define your scope, and stick to it, and by doing so you’ll avoid this issue.

In our opinion, scoping early and often — and holding people to an agreed scope — is one of the most important skills in legaltech, legal ops and innovation (and any project generally)!

Enforcing constraints on activities through scoping — e.g. controlling what is and is not in scope — isn’t easy, and often uncomfortable, but well worth the effort to avoid storing up larger problems, especially scope creep and mismanaged expectations, which are each very hard to reset once they arise!

03. Process Mapping & Measurement

A process map is a planning and management tool.

A process map visually describes the flow of work in a system.

Process maps show a series of inputs, teams and / or individuals, and events that produce an end result.

A process map is also called a flowchart, process flowchart, process chart, functional process chart, functional flowchart, process model, workflow diagram, business flow diagram or process flow diagram.

Still confused? Here’s one we made earlier for a typical NDA process:

In a nutshell it shows who does what, how, where, with whom, when and why in a process and can be used in any business or organization.

Process maps are ideally mapped collaboratively among the relevant stakeholders to a process, which helps align everyone’s understanding of the process, which may otherwise differ if developed in silos.

You’d be surprised about how differently stakeholders to a single process can view a shared process!

Processes should also be measured to understand key metrics about their performance, and to provide insights about the flow of inputs, processes and outputs.

Measured process maps are sometimes known as value stream maps.

Value stream maps display all critical steps in a specific process and quantify the time and volume at each stage. This can be a great way to understand the flow of both materials, people and information as they progress through the process… and by further analysis, whether the flow is efficient or inefficient, and in turn how this might be improved!

Returning to the above NDA example, to transform that process map into a value stream map you might measure things like:

• The number of NDAs processed by the workflow in a given period, e.g. a day, week, month, quarter, or year.
• The time it takes for an NDA to pass through each step in the process, and the overall time it takes for the process to complete per NDA.
• The number of people involved in aggregate, or at specific steps.
• The number and type of steps involved, e.g. handovers between individuals, document versions, negotiation back and forths, escalations and so on.

Process maps, whether measured or not, provide a way to identify areas for improvement, usually parts in the process where the flow gets snarled up, aka bottlenecks, or could be sped up.

These opportunities to improve the process often present as the 7Rs, i.e. opportunities to:

• Rethink
• Reconfigure
• Re-sequence
• Relocate
• Reduce
• Reassign
• Retool

This usually leads to a redesigned process, or desired state (aka to be) process.

Going through this exercise of first mapping the current state and using that to develop a desired state process makes it easier to plan and prioritise what and how to improve the process.

There are many related methodologies that prescribe different process mapping exercises, purposes and visual elements to represent systems.

Rather than being too focused on these at first, it’s best to get a general understanding of the business purpose of process mapping and to start doing it!

A great way to do this is to map a simple process you work with every day and analyse it for improvements. Don’t get too fixated on the exact flowchart elements to use — just start mapping! You will have much more understanding of your own process so long as you clearly capture the order of who does what, when, how, where, with whom and why.

For a primer on a related topic, that of Lean — a famous set of techniques and principles (including process mapping and measurement) devised by Toyota to optimise its processes, we recommend This is Lean or, for a more in-depth guide, The Toyota Way.

04. Business Analysis

Business analysis is a wide ranging activity intended to understand the current state of an organization or process. This will be used to understand how this differs from a desired, or future, state that the business strategy is seeking, or may simply be considering.

Often using the above activities (scoping, process mapping and measurement), business analysis will dive deeper into an existing or desired process (or an entire organisation’s operating model) to understand the inputs, processes and outputs and answer basic questions like who is doing what with whom, when, where, how and why.

They may also attach detailed financial costs and calculations to all of the components in the overall business system to understand its economics.

At a high level, there are usually at least 3 key questions to answer, which will be:

1. What is the “as is” state of the process or organisation, and is it effective at achieving its objective(s)?
2. What “to be” state might improve things (assuming the current state is suboptimal)?
3. What steps successfully transition the process or organisation from (1) to (2)?

From this, the person performing business analysis will build a detailed picture of the current state of the business and use this, through stakeholder engagement and alignment with the business strategy, to develop a desired state of the business, or measure the current state against a predefined desired state.

To understand the steps between current state and desired state a gap analysis may be performed to assess the specific differences between the two.

Understanding the difference between current and desired state (i.e. the gap) will inform what steps (and action plan) are needed to bridge the gap and transition the process or wider organisation from current to desired state.

This will invariably require significant change management (see below), especially if — as is often the case — the necessary changes impact jobs, roles, reporting lines and responsibilities.

Business analysis in legaltech, ops and innovation crops up where an organisation is seeking to improve its legal function, or advise a client on how to do the same.

05. Service Design & Design Thinking

Service design is the activity of planning and organizing people, infrastructure, communication and material components of a service in order to improve its quality and the interaction between the service provider and its users.

The previously described activities (scoping, process mapping / measurement and business analysis) often form a part of this overall activity of service design, along with design thinking.

Design thinking typically involves facilitating and managing the following set of steps when identifying both: (a) problems to solve; and (b) ideas for solving those problems:

• Empathize. Directly observing what users do, how they think, and what they want, asking yourself things like ‘what motivates or discourages users?’ or ‘where do they experience frustration?’ The goal is to gather sufficient observations that you can empathize with your users and their perspectives and drivers. If you can’t understand, you can’t help!
• Define. Combining research (see above) to identify where your users’ problems exist. In pinpointing your users’ needs, you can begin to highlight opportunities for innovation. In this phase, you will be looking for common pain points and opportunities to solve unmet needs.
• Ideate. Brainstorming a range of creative ideas that address the unmet user needs identified in the define phase. No idea is too far fetched at this stage. Quantity supersedes quality. Mixing and remixing of ideas is encouraged. The aim is to be creative, and think outside the box.
• Prototype. Build real, tactile representations for a subset of your ideas. The goal is understanding what components of your ideas work, and which do not. In this phase you begin to weigh the impact vs. feasibility of your ideas through user feedback on your prototypes.
• Test. Return to your users for feedback. Ask ‘Does this solution meet users’ needs?’ and ‘Has it improved how they feel, think, or do their tasks?’. Get your prototype testing with real customers and verify it achieves their goals and yours. Does it improve their experience?
• Implement. Put the vision into effect. Ensure that your solution is enacted and touches the lives of your end users. This may require that you build out user training, marketing, and case studies to drive adoption. With a few exceptionally rare exceptions, great products don’t always sell themselves. You will need to sell (see below)!

Service design and design thinking skills and activities can be a great way to surface unheard voices within teams or organisations. The collaborative elements, particularly in the earlier stages of such processes can democratise ideas, and the means for surfacing and actioning them. That said, this feature of such activities can be a reason for resistance, i.e. people not wanting to share decision making influence with others. It’s not a deal breaker, but something to be mindful of when trying to introduce these concepts to legal organizations! Recognising this is actually part of change management (see below), i.e. pre-empting and navigating objections to drive change.

For a great resource on service design, we recommend the book This is Service Design Doing.

06. Product Management

Product management overlaps a lot with the above activities, which are often necessary tools in a product manager’s arsenal, both to identify unmet needs but also to test and develop new ideas for products.

Product management is about:

• Identifying the customer need and the larger business objectives that a product or feature will fulfil, articulating what success looks like for a product, and rallying a team to turn that vision into a reality.
• Representing and articulating those user needs to other stakeholders, e.g. sales, developers, marketing etc, and aligning stakeholders around the product vision. Getting their buy-in is often crucial to progress product in the right way.
• Monitoring the market and developing competitive analyses; whilst you shouldn’t slavishly follow competitors, ignorance of their activities is not to be encouraged.
• Prioritizing product features and capabilities, often involving the creation of a shared brain across larger teams to empower independent decision making. Tools like Jira, Asana, Trello and similar may be useful.
• Defining and maintaining the product roadmap (i.e. the forward looking deadline driven list of prioritized product features), and product backlog (i.e. the to do items to address previous product roadmap objectives as well as upgrades and fixes).

For some good reads on what makes excellent products, we recommend the following:

Product Management 101

• The Product Book by Josh Anon. Based upon Product School’s curriculum, which has helped thousands of students become great product managers, The Product Book is filled with practical advice, best practices, and expert tips collected from product managers at leading companies, and the author was himself a product manager at Pixar. This is a good starting point to understand the discipline and the role.
• Cracking the PM Interview by Gayle McDowell. This is a popular choice for individuals seeking to plan and prep for product management interviews. Like the equally popular Cracking the Coding Interview (worth a read if you are preparing for developer interviews), it’s a mix of inside advice from the world’s largest tech and product companies, distilled into actionable activities and exercises to focus your skill acquisition and development as a product manager, whether or not you are preparing for a specific interview or interested in understanding the skills for this type of role and what employers look for and test.
• Sprint: How To Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp, John Zeratsky and Braden Kowitz of Google Ventures. Describes Google’s five-day process, where sprints (a type of product management methodology) are used on everything from Google Search to Google X.
• Shape Up: Stop Running in Circles and Ship Work that Matters by Ryan Singer, head of strategy at Basecamp. The team behind Basecamp have produced several excellent no BS books on start-ups, product management, getting finance, building teams and scaling. Shape Up is their latest. They’ve managed to create hugely successful product driven businesses whilst remaining lean and not working themselves to death. Sounds good right? Learn more by reading the book — available for free or in print.
• For some great FREE product management resources, including templates and similar, we recommend this compendium of materials as a useful resource.

Product Management Theory

• Inspired by Marty Cagan addresses the single most important question for product companies: how to create successful products and what determines success vs. fail? Filled with case studies spanning Google, Tesla, Netflix, Amazon and many more, Cagan unpicks what drives success.
• Hooked by Nir Eyal identifies why some products capture our attention while others flop. Eyal reveals what makes us engage with certain things out of sheer habit and provides a four-step process that, when embedded into products, subtly encourages customer behaviour that is habit forming. A Eyal concludes, these methods can form virtuous or vicious customer habits, so should be treated with caution. Will make you reassess your relationship with many products, especially social media!
• Jobs to be Done by Jim Kalbach examines the theory of jobs to be done, the idea that products are temporary solutions to a much more long term need, motivation or job that a customer has. This was famously described by Theodore Levittt (made popular by Clayton Christensen) as the idea that people don’t buy a drill, they buy a quarter inch hole, and that understanding the reasons behind a buying decision provides valuable insights to business and product managers.
• The Lean Start-up by Eric Ries, (in)famously associated the build fast, break things mantra of Silicon Valley entrepreneurs is — like a lot of popular books — often misunderstood and misapplied. Despite its detractors in recent years, it remains a good read for any budding product managers or founders. Its thesis is that rather than wasting time creating elaborate business plans, The Lean Startup method instead offers companies of all sizes a scientific method to test their vision continuously, to adapt and adjust before it’s too late.
• The Lean Playbook by Dan Olsen is a practical guide to building products customers love aimed at product managers at big or small companies. Olsen wrote this book to close the gap he observed between The Lean Start-up and a concrete, repeatable, easy-to-follow methodology for building winning products.
• Crossing the Chasm by Geoffrey A. Moore is a classic. It explores how to bring cutting edge products to market and the challenges of moving from early adopters into increasingly larger and more lucrative markets without crashing and burning, i.e. crossing the chasm between those market segments. A must read for product managers and business managers trying to scale.
• The Innovator’s Dilemma by Clayton M. Christensen is the best selling read on disruptive vs. sustaining innovation and how businesses and products can do everything right, yet still fail. Christensen explores how and why this happens and provides targeted solutions.

07. Project Management

Project management is the application of processes, methods, skills, knowledge and experience to achieve specific project objectives according to the project acceptance criteria within agreed parameters (e.g. constraints such as budget, timescale, available technology or materials, available people etc).

Project management activities can include:

• Defining the reason why a project is necessary, e.g. sometimes requiring a costed business case.
• Capturing project requirements, specifying quantity and quality of the deliverables, estimating resources and timescales (i.e. scoping).
• Securing agreement and funding.
• Developing, implementing and communicating a management plan for the project (together with updates as and when they arise).
• Leading and motivating the project delivery team and their stakeholders.
• Managing the risks, issues and changes on the project.
• Monitoring progress against plan.
• Managing the project budget.
• Maintaining communications with stakeholders and the project organisation.
• Provider management, e.g. managing interactions with product or service providers and interactions between those and other teams, such as procurement and so on.
• Closing the project in a controlled fashion when appropriate.

In other words, this is about being the organiser and being organised! Naturally, building a product is a type of project, so a lot of project management skills and activities form a core component of good product management.

08. Programme Management

Program management or programme management is the process of managing several related projects, often with the intention of improving an organization’s performance at a more macro level, e.g. a division’s performance or perhaps the entire organisation’s performance! Programme management might also come into play when launching into a new market, i.e. because several interrelated projects are necessary to launch and build in that market.

To be clear, here’s an example of a project vs. a programme:

• A project. Improving the NDA process for an organisation, from cradle to grave, aligned to a micro need, e.g. spending less time and money on NDAs and freeing up legal resources for higher value tasks.
• A programme. Improving all contracting and other legal processes for an organisation, aligned to a macro need, e.g. reducing legal spend through improved legal operations generally. This programme will involve projects like the above NDA project, but also others, e.g. a process improvement project for sales agreements, contract renewals, revenue assurance and so on as each relate to legal operations. The aim is to improve the entire division’s performance at their function, i.e. legal support in general.

Skilled and experienced project managers often graduate into programme management roles.

09. Stakeholder Management

As is hopefully obvious from the above activities, being able to manage a variety of stakeholders in terms of seniority, business division, incentives, politics and so on is critically important.

Being able to identify, anticipate and pre-empt objections or internal politics and deftly navigate these through influence and persuasion (see below) helps an individual or team achieve their objective. A lot of this comes down to clear, targeted, timely and empathetic communication. Often this will involve getting the right people to have the right conversations at the right time.

For example, if Susan manages NDAs and is bonused based on how many billable hours she bills how will she respond if you bluntly inform her:

You must use an AI service that can do 75% of your job in 2% of the time it takes you to do 100% of your job absent of the AI service.

Some finesse will be required to articulate the benefits, e.g.

• Being able to handle more volume such that billable hours remain static or improve and therefore bonuses remain achievable rather than decimated.
• Being able to do less repeat work, having that delegated to the AI.
• Being able to do more higher value work, e.g. handling edge cases not run of the mill etc.

If Susan is a manager of a team of reviewers, you may need to help Susan communicate these messages to her team.

You may need to rethink the wider business structure, perhaps redesigning incentives so that output is focused on prioritising the quality (i.e. efficiency) of billable hours rather than the quantity… you might even need to dispense with billable hours altogether (the horror!), designing fixed fee pricing based on value and aligning individual incentives to that new pricing model.

As technology is being introduced, you will need to help your organisation’s IT and security folk get comfortable that the technology isn’t a risk, or a burden to maintain. And because you are buying something, you will need to loop in procurement. Ideally you want procurement and IT security looped in early to avoid delays to getting Susan the tech you promised her and team.

If you get the messaging, order or combination of individuals muddled (let alone miss something or someone out), progress can get derailed or obliterated entirely, e.g. if someone is put out and decides to squash you or your project.

10. Influence & Persuasion

Getting a job done, whatever the job, will require influence and persuasion.

This is particularly relevant in legaltech, ops and innovation where you will be challenging the status quo and trying to encourage behavioural change.

This is even harder in legal where the stakeholders, culture and organisations involved bias heavily toward risk aversion and precedential incrementalism, both in the products and services they provide and how they provide them, but also in terms of how they think about internal change.

Understanding how to influence and persuade is key.

A good primer on time tested techniques, generally applicable to most situations, is Robert Cialdini’s famous book, Influence as well as his follow-up, Pre-suasion.

The key lessons from those books are summarized below:

11. Communication

And of course, you can’t do any of the above, nor anything that follows without excellent written, oral and visual communication skills. Communicating ideas and influencing people toward action requires mastery of good communication. We won’t spend too much on this skill as it’s well documented elsewhere.

What we would say is that lawyers in particular can and should focus on improving their visual presentation skills.

Why?

When you look around you, the world’s most impressive leaders, change agents, products and services tend to have a strong visual element.

However, most lawyers — and those working in legal — tend to overlook, and be generally poorer at visual presentation skills. You only need to attend a few legal or legaltech conferences to confirm this. Likewise, how many law firm pitch decks have you seen that look like they were made in the late 90s or early 00s, overladen with text and old school graphics?

Granted, this has improved a lot in the past 5 years or so, but truly impressive visual presentation of the type demonstrated by world leading thought leaders and product companies remains a minority ability within legal.

This presents a huge opportunity for those willing to improve their visual presentation skills.

For some ideas on where to start, we highly recommend you check out this podcast, via the Advocacy Podcast, with litigator Justin Kahn, about how he combines the visual presentation techniques of Steve Jobs and similar with the latest learnings from neuroscience and even stage magic to be a more effective litigator, both in terms of how he designs his arguments but also in how he presents them to judges and juries. Fascinating stuff, with lots of recommendations and great advice!

For those interested in selling ideas, whether their own internally or as a founder or product person, we recommend this useful compendium of pitch decks from companies that are now billion dollar unicorns.

12. Networking

As with any business domain, the best succeed via strong networks. Networks should be thought of in two ways:

• internal networks;
• external networks.

Internal networks

Internal networks are the individuals within an organisation with which you need to build relationships in order to get your job done. If you are in a legal ops or innovation role within a law firm or large legal team you can’t effect change without an internal network.

Likewise, if you are at a vendor in a sales role, you can’t be successful without having a good relationship with product (to ensure you understand the roadmap and have a voice in its development) and in-house legal (to ensure your sales contracts get reviewed in a timely manner).

Why?

Many legaltech, ops and innovation projects require a rich tapestry of individuals and teams to get sh*t done. If you don’t invest in people, you won’t have much luck at the process and technology!

External networks

External networks comprise your peers and supporting players in your domain. In legaltech, legal ops and legal innovation this might be technology vendors, innovation or ops teams at peer organisations, thought leaders, event organisers, meet-up groups and so on.

So why network externally?

Legaltech, ops and innovation is a changing field. Technologies that were all the rage today might be forgotten weeks later. There is already an increasingly crowded graveyard of legaltech. Staying on top of the latest developments and opportunities (whether jobs or otherwise) is all about networks.

If you truly find legaltech, legal ops and legal innovation interesting, building your external network will be fun, engaging and easy. It’s surprising how much more fun networking is if you actually enjoy your domain! The other thing to say is that inherently collaborative domains, — such as legaltech, legal ops and innovation — tend to engender collaborative rather than competitive networking culture and environments.

If you are a lawyer coming to legaltech and similar, you’ll be surprised at how much more collaborative, open and friendly networking events are vs. typical legal ones!

A word of warning…

Legaltech, legal ops and innovation remains a relatively small niche, so be nice and treat people with respect. You’d be surprised how small the market is and how well everyone knows each other, even globally!

13. Data Science

Data science is an interdisciplinary field. Data science combines scientific methods, processes, algorithms and systems to extract knowledge and insights from structured and unstructured data, and apply that knowledge and those actionable insights from data across a broad range of application domains.

Data science will typically involve some form of data derived deliverable, e.g. any one of the following might be typical:

• Prediction, e.g. given the square footage of a house, predict its price.
• Classification, e.g. spam or not spam.
• Recommendations, e.g. Amazon and Netflix recommendations.
• Pattern detection and grouping, e.g. classification without known classes.
• Anomaly detection, e.g. fraud detection.
• Recognition, e.g. image, text, audio, video, facial, etc.
• Actionable insights, e.g. via dashboards, reports, visualizations etc.
• Automated processes and decision-making, e.g. credit card approval.
• Scoring and ranking, e.g. credit scores.
• Segmentation, e.g. demographic-based marketing.
• Optimization, e.g. risk management.
• Forecasts, e.g. sales and revenue.

Data science requires a dataset, i.e. set of data to analyse and process and thereby deliver one or more of the above.

Sometimes data scientists will be given a nice and appropriate dataset to begin with, but in most cases, this isn’t the case.

Instead, the data scientist will need to acquire, clean and organise that dataset, or help someone step through those actions. This is the most time-consuming part — sometimes as much as 70% of a data science project’s time will be spent on this part of the process.

Having the right quality of data in the right quantity is critical — without it, there’s nothing or very little to work with!

What does a typical data science project look like?

A typical data science project looks like the below:

If you want to learn more about this workflow, including who does what, how, when, where and why in a data science project, we recommend you check out the below 5 part series detailing a typical data science process.

Part 1 — High Level Introduction

Part 2 — Defining the Project

Part 3 — Acquire, Understand and Prepare the Data

Part 4 — Modelling and Evaluation

Part 5 — Deployment and Feedback

It’s a great series, and absolutely accessible to anyone (no coding, maths or data science skills required)!

But hang on, why is data science relevant to legal?

Legal is fundamentally a knowledge business.

Most law firms have established knowledge management (KM) functions dedicated to the creation, capture, curation, organisation and retrieval of legal information and are starting to apply data science to that knowledge, both to create new knowledge and to drive insights and decisions based on existing data.

The growth of legal AI applications and their widening popularity, e.g. such as Kira Systems, has also thrown into sharp focus the increasing importance of data science to law, and the need for excellent information architecture.

What’s information architecture?

Information architecture is the creation of a structure for a website, application, or other information system, that allows users to understand where the information we want is located in relation to our position in that system.

In many ways, information architecture is about making information both findable and usable.

Information architecture results in the creation of interfaces, site maps, hierarchies, taxonomies, ontologies, categorizations, navigation, search algorithms and metadata.

When a content creator or curator — including a knowledge management lawyer — begins separating content and dividing it into categories, they are practicing information architecture.

When a designer sketches a top level menu for an app to help users understand where they are on a site, they are also practicing information architecture.

Regardless of what task is being accomplished, the below are typical questions that information architecture aims to ask and answer:

• What is the flow of users through our system?
• How does the application help the user catalog their information?
• How is the information organised, searched, filtered, sorted?
• How does the user know what actions to take in order to retrieve the information they require in the desired format?
• How is that information presented back to the user?
• Is that information helping the customer, and driving decisions?
• How does the system need to cater for information growth and decay (i.e. the decreasing relevance of information as it becomes older and replaced by newer information)?
• How does the information need to interoperate with other systems, users and use cases?

Summary

A lot of legaltech, ops and innovation roles therefore increasingly require some level of data science awareness, or at least a willingness to engage with it and those professionals expert in it.

14. Data Analysis

Sometimes confused with data science, partly because data science often requires data analysis, this is in fact an often separately applied skill. It’s also necessary when thinking about many of the other activities described here.

To provide a concrete example in legaltech, ops and innovation, if you are rolling out a new technology (having done the prior people, process and technology analysis beforehand), you will want to gather data about the technology and its adoption:

• Is anyone adopting?
• Who is adopting it?
• Why are they adopting it?
• Why aren’t they adopting it?
• How often are they using it?
• How many people convert from an emailed training invite to attendance at your training sessions?
• Of those who attend training, how many go on to create an account and start using the product (i.e. become activated and active users)? And so on.

If you gather, analyse and present this data well you will better understand what is or isn’t working and why.

This data analysis may also be used to solve adoption problems. An example might be to provide concrete ROI figures to persuade users to adopt X over Y, e.g. if X improves some incentive aligned metric, perhaps saving significant time, reducing costs, generating significant profit, improving top line growth, increasing client wins vs. competitors etc.

15. Selling

“No matter what you do in life, selling is a part of it” — Arnold Schwarzenegger.

Why’s that?

Whatever you do, you always have to sell one thing: yourself. And by extension, your ideas, and if you work in a company, a product or service.

Sales has a bad reputation.

We often think of the cliched sleazy used car salesman, trying to sell an unsuspecting prospect a doozy of a car.

Sure that still happens. But great salespeople are so much more. Great sales people exhibit at least these abilities:

1. They know their domain, whether it’s their idea(s), their team or their product.
2. They listen first. Two ears and one mouth in that ratio!
3. They ask questions and are curious about others; they seek to understand motivations, drivers, constraints, politics, incentives and disincentives.
4. They preempt objections, foresee roadblocks and try to help customers make decisions.
5. They are people focused: able and interested in building and maintaining relationships to get stuff done.
6. Have a thick skin, persistence and a drive to grow and succeed. They know how to spot good partners and bad partners, and to invest in the former and avoid the latter.

Lawyers can often be quite sniffy about salespeople, and the idea of selling in general. It’s not unsurprising given that, for the most part, sales skills do not factor in legal training, whether at university, college or on the job.

But overlook sales skills at your own peril.

If you get good at sales, you’ll be better at selling yourself, your team, your idea, product or service. In legaltech, ops and innovation you’ll always be doing at least one of those things, and more often than not, most of them.

As Peter Thiel, Paypal founder and famous Silicon Valley investor, stresses in his highly recommended book Zero To One:

Even though sales is everywhere, most people underrate its importance. Silicon Valley underrates it more than most… What nerds miss is that it takes hard work to make sales look easy… Poor sales rather than bad product is the most common cause of failure.

by Peter Thiel in Zero to One

And Thiel’s point is generally true of any idea: if you think it, they will not come.

You need to sell people on your idea. That idea could be your value as an individual (for a job or promotion), your team’s project or your own product or service!

Legaltech, legal ops and innovation roles involve juggling and assessing new ideas, and usually persuading others to adopt those ideas and make them their own. You won’t be effective in those activities without being able to sell.

16. Marketing

Tied closely to sales is marketing. Marketing, like sales, is the process of understanding your customers, and building and maintaining relationships with them.

Like sales, this presents as activities undertaken to promote the buying or selling of a product, service, individual, team or idea.

Marketing often entails research to understand a market, a customer or set of customers and their needs and wants, which is then used inform decisions about product, sales and the general marketing strategy, i.e.

• Who should we target, e.g. people aged 25–35, single mums, fitness fanatics etc.
• How should we target them, e.g. ad copy, messaging, articulation of a problem and solution etc.
• Where do we target them, e.g. online, traditional media, viral stunts etc.
• When do we target them, e.g. before Christmas, during Superbowl breaks etc?
• Why are we marketing in X or Y manner and is it working, e.g. A/B testing?

Naturally, like sales, marketing is about influence and persuasion — getting people to buy-into something, and building and maintaining a relationship with those people in order to do so, and as a means to keep them happy and engaged with whatever that thing is.

In law firm legaltech, legal ops and innovation roles marketing can play a big part, both internally and externally.

Internally, marketing can be used to promote awareness and drive adoption of new ideas and technologies.

Externally, marketing can be used to advertise the innovation or operational excellence qualities of a firm, e.g. in RFP / RFI responses, pitches and other outward facing presentations and client interactions as a means to influence buying decisions or elevate the firm’s brand with innovation minded customers.

17. Operations

Operations management is about designing and controlling the means of production within a business.

Unsurprisingly, operations is about ensuring those means are, and remain, as efficient as possible, usually in the sense of delivering on their objectives, whether that is speed, quality, quantity, cost or profit.

Applied to legal, “legal operations” or simply “legal ops” as it is known, means running a legal function like a business.

The Corporate Legal Operations Consortium (CLOC), one of the leading industry bodies focused on legal ops for in-house legal teams, has a framework of 12 competencies.

These are:

In brief, these breakdown as follows:

• Business Intelligence. Determining the right data to collect and monitor about the legal function’s operations. Designing and rolling out metrics and dashboards to track suitable metrics and use these to inform decision-making about how to improve the legal function.
• Financial Management. Developing and maintaining a budget as a means to monitor costs and identify opportunities for savings and efficiency, including with regard to any outside legal spend.
• Firm & Vendor Management. Developing and maintaining valuable relationships with third party legal services vendors, including law firms. Designing effective RFPs and negotiating positive pricing models with third party providers.
• Information Governance. Designing and implementing clear and comprehensive policies and systems for information governance, in particular determining which physical and digital documents should be preserved or destroyed in compliance with any regulatory or other internal requirements.
• Knowledge Management. Creating systems and best practices that save the team time and improve outcomes by making it easier to find answers, best practices, precedents, templates and other knowledge.
• Organization Optimization & Health. Building teams and progression structures that attract and retain a diverse range of talent, not just lawyers.
• Practice Operations. Implementing systems and processes that free up legal resources for higher value work via elimination of lower value, work. Using specialist resources for specialist tasks, such as for eDiscovery or document automation. Using augmentation or automation of processes wherever possible, enabled by greater standardisation.
• Project/Program Management. Running department-wide and sometimes company-wide initiatives tackling complex special projects, e.g. tackling a macro repapering challenge such as the discontinuation of IBOR in a financial services business.
• Service Delivery Models. Designing service delivery models that ensure the right resource is applied to the appropriate task complexity. Creating a complementary system of vendors or alternative service providers, such as ALSPs, and thereby reducing spend on traditional outside counsel where appropriate.
• Strategic Planning. Defining the strategic vision and planning its execution, both in terms of short and long term opportunities and priorities for the legal function. Aligning these to company-wide objectives and KPIs where necessary.
• Technology. Using technology to streamline processes and time spent per task by automation the most time-consuming and overly manual tasks undertaken by the legal function. As part of this, determining selection criteria and applying these to select, test and implement appropriate vendors into your legal function. Understanding emerging technologies and staying up-to-date on the latest developments and how these can be applied to the legal function’s processes.
• Training & Development. Designing and implementing targeted training, covering hard and soft skills as well as any required compliance training.

Mastering the above competencies, and operations generally, entails a deep understanding of inputs, process outputs, incentives, culture and strategy. As such, many of the abovementioned activities, research, scoping, process mapping / measurement and data analysis in particular are used in operations, whether for legal operations or general business operations.

To bring this to life, we recommend you check out this fantastic podcast with Mary O’Carroll, Director of Operations, Technology and Strategy for the legal department at Google and President of CLOC. It provides great insight into the legal ops function, and Mary is one of the pioneers of this role and has built a world renowned legal ops function at Google.

The entire podcast series, focused on legal ops, is also well worth subscribing to for those interested in legal ops and roles in that space. It’s run by Alex Rosenrauch, a Manager in PwC’s New Law business, and Eliot Leibu, head of legal operations at Australian bank, ANZ.

18. Strategy

Strategy is the formulation (and sometimes also implementation) of the major goals and initiatives taken by an organisation’s management, on behalf of its stakeholders, based on a consideration of available resources and an assessment of internal and external environments in which the organisation operates.

Traditional management theory usually separates strategic management and operational management. The latter being what we’ve described as operations above.

In reality, there is often some overlap between the two.

For instance, a business strategy may be to improve efficiency as part of a drive to enter new markets where the current costs of production don’t make sense economically in that new market. For those types of project, the traditional boundaries between strategic and operational management may be more blurred.

In legaltech, ops and innovation, strategy can take various forms depending on the organisation.

For a legal organisation, strategy as it relates to legaltech might mean whether or not an organization’s strategy is to be, and to be seen as, an innovative legal services provider and how to go about building that market perception and why it is important to do so.

For other legal organisations, simply being seen as innovative without actually being innovative might suffice!

It’s key your organisation has decided which it is to be, is honest about this (at least internally) and that this is communicated correctly internally and externally!

For a legaltech vendor, strategy may be about which markets to expand into, or which features or products to prioritise, which naturally dovetails into product management.

19. Change Management

Change management ecnompasses all activities to prepare, support, and help individuals, teams, and organizations in making organizational change.

What drives change? Many things. Change may be driven by the ongoing evolution of technology, internal reviews of processes, crisis response, customer demand changes, competitive pressure, acquisitions and mergers, and organizational restructuring.

Change management activities will entail the redirection or redefinition of resources, business process, budget allocations and so on.

In legaltech, ops and innovation you will often be introducing new ideas, ways of working or technology. This change can be anxiety inducing for those involved, who may have vested interests in their current modes of working.

For example, if a technology reduces time per task for an employee who has a billable hour target, you are reducing their ability to meet their target, receive a bonus and generally earn favourable reviews and progress in their career.

Simply demanding they use said technology without more will lead to change management failure unless you understand and anticipate this concern, and provide and prepare the individual and organisation for the change, which may require a reassessment of that individual’s incentives and a cultural reset focused on efficiency operations, i.e. quality not quantity of hours etc.

Change management seeks to address these issues and clear a smooth path for change.

A popular framework is John Kotter’s change management principles:

For a deeper dive into these techniques and frameworks, we recommend Kotter’s main books, which are:

• Leading Change. The original book that popularised Kotter’s above 8 step change management framework.
• Our Iceberg is Melting. Kotter uses a charming story about a penguin colony in Antarctica to illustrate key truths about how we deal with the issue of change: handle the challenge well and you can prosper greatly; handle it poorly and you put yourself at risk. Sounds silly, but trust us, it’s very relatable and actionable!

20. Software Development

Software development is a process of writing and maintaining the source code (i.e. coding), but in a broader sense, includes all that is involved between the conception of the desired software through to the final manifestation of the software.

That process spans the activities of conceiving, specifying, designing, programming, documenting, testing, and bug fixing that are necessary to create and maintain software.

This unsurprisingly requires research activities, design thinking, product management, project management and scoping.

In legaltech, ops and innovation you are mostly likely to see this activity vendor side.

That said, many legal organisations — including law firms — have their own in-house development teams. However, those teams tend to focus more on enterprise applications concerns, i.e. keeping existing applications up and running and maintaining or building integrations between each system. In a minority of cases, they may design, build and implement custom software specifically for their organisation, or rarer still, a client facing SaaS product!

21. Training & Education

Legaltech, ops and innovation often involves a lot of education and training, whether that’s training users on a new technology or upskilling them into some of the activities described above and associated mindsets.

An example of the above might be a workshop designed to teach lawyers design thinking skills, and better yet, apply them in solution to a problem those skills help them identify and understand.

Training and education may also take the form of being a domain expert, usually in a technology (e.g. AI or blockchain), and helping lawyers understand the tech in enough detail such that they can formulate precise legal advice as to how legal rules or regulations do or do not map to an emerging technology or a particular use case.In some cases you may be training customers (e.g. working at a legaltech vendor) or clients (e.g. getting a law firm’s clients up to speed on how to use a collaborative deal management platform). Unsurprisingly, good communication skills, in particular visual communication will serve you well.

⚡ Don’t forget the rest of the guide ⚡

This article forms part 4 of our 6 part series on careers in legaltech, legal ops and innovation. Please check out the other articles and career profiles for more inspiration and guidance!

Originally published at lawtomated.

In this piece we chat to Sam Smolkin of Office & Dragons about Transaction Development, or how to design deals like software and thereby save a ton of time whilst creating a wealth of value for clients and lawyers alike.

What is Transaction Development?

Transaction Development is a way to deliver deals. At its core, it is a shift in mindset — rather than focusing on drafting and negotiating various documents like Share Purchase Agreements or Senior Facilities Agreements, you think about transactions as a set of deal terms, or data, which can be visualised in various ways, such as clauses in various contracts, steps in a tax structuring powerpoint, or points in a post-closing governance memo.

It’s moving our thinking one level up: rather than thinking about how individual documents or sets of documents are constructed and produced, we’re thinking about how deals are constructed and delivered as a whole.

Thinking about deals, rather than documents, leads to greater efficiencies. Rather than creating templates one at a time for just the work we’ve done frequently before, we can put in place a framework that guides and supports the way deal terms are developed and contracts are produced for any deal, even where all the contracts are new and bespoke.

So, it starts with a better process, and that alone can save a lot of time and improve accuracy as you rationalise away redundant steps and error-prone procedures from your workflows. On top of that, we can build technologies leveraging that framework to automate away the toilsome manual processes which remain.

We achieve these efficiencies when we separate out the key deal terms from the documents that they appear in during the negotiation process. Keeping the deal terms separate and in one place until we’re ready to sign the contracts, rather than writing and updating them directly and repetitively into various document pages, makes it quicker and easier for everyone to align on terms and make sure they’re reflected correctly in the final form contracts and other work products created for the deal.

If we’re working this way, we’re also capturing data about the deal in real-time as it develops. We don’t have to spend a bunch of time and money trying to find it in the documents afterwards (whether it’s expensive lawyers or expensive AI tools doing the digging), and we can use it to provide valuable insights to our clients (and stand out from our competitors who can’t do so as quickly).

You talk about a shift in mindset. What led to conceptualising that mindset and applying it to law?

This concept isn’t new; it’s a core principle of modern software engineering whereby software engineers decouple the data (the information) from the view (the presentation of the information).

It’s also known as the separation of concerns, i.e. breaking up a system into component parts such that each part does one thing and one thing only.

This principle is the backbone of software engineering patterns like Model-View-Controller (MVC) and software development frameworks like Angular and technologies like the Angular compiler.

These frameworks and technologies are what make it possible for software developers to rapidly develop the many different apps we all use today — there are reasons we have so much more software today than we did a couple decades ago, and this is a big one.

The speed of development doesn’t stem from standardising the applications, but from standardising the way they organise information while working — where the data, the business logic and the presentation elements go. This allows many developers to work together efficiently without having to dig through each other’s code to find relevant information, and to develop technologies based on these “standard formats” to speed up the work.

Separation of concerns (if this remains unclear, see below expandable section) also makes it far easier to re-use and update systems built in this way. It also provides greater control over how changes to one part of the system do and don’t affect the other.

Up until now, this is not how contracts are created and updated, nor how a transaction is thought about (including its underlying contractual components).

Instead, each contract in a transaction has no link to a common data source representing (in technical terms, modelling) the transaction’s key terms. This means that if you change the amount of a loan in the loan agreement, references to that figure in any related documents — such as the security documentation — remain unchanged and instead require individual manual updating. This is because there is no common data model to the transaction and separate from the various presentations of that data, i.e. the contracts comprising the deal.

Help me out — what actually is separation of concerns? A worked example

Modern websites employ separation of concerns so that you can update the underlying data once and have those changes automatically rendered in each place and on each web page where that data is presented vs. having to make the same change one by one across multiple pages. Conversely, this also allows you to update the interfaces (e.g. web pages for a website) without upsetting the underlying data that such interfaces present to the user.

Let’s use the example of Amazon to explore separation of concerns, before seeing how this has parallels with modern contract drafting.

Changing data without upsetting the presentation

If I were browsing for The Lord of the Rings Blu-ray boxset, that product listing will also highlight other items I might consider buying, eg.

These items all display several pieces of data (the item name, price, star rating, leading actors) stored in Amazon’s inventory database. In a lot of ways, the way in which one item’s listing will refer to other item’s listings is akin to how one contract cross-references data in one or more other contracts, e.g. a defined term or important obligation.

If Amazon wanted to change a piece of that data (say, apply a 15% discount to all Lord of the Rings products for Black Friday), they simply need to access the database that contains the data for each of these products and make a single change (e.g. run a command that reduces the price of all Lord of the Rings items by 15%) in order to update the entire store, including every place across every page on Amazon’s website where this information is listed, ie. both the item’s individual listing and any cross-references to that listing in any other item’s listings (as above).

Without separation of concerns this data might be hardcoded into each individual page in which that item’s data appears (including recommendation bars like the above), creating multiple and separate copies of that data. In that scenario, somebody on the merchandising team would need to go to every single page that a product might appear in to double check that the price is reflected correctly across the site — they couldn’t make one change and have it automatically updated across the site. This setup would make no sense because Amazon’s website is necessarily in constant flux, being updated to reflect market pricing, changes to inventory and recommendations based on user interactions.

Changing the presentation without upsetting the data

Now, if Amazon also decided that the “Customers who viewed this item also viewed” bar should not have any star rating data displayed, i.e. a change in the presentation of data, a single programmatic change can remove that piece of data from the user interface without deleting the underlying data. The data still remains in the database, and will appear anywhere else in the site that they want, but for that bar, the data will not be displayed.

Without separation of concerns, if that data was hard coded into the interface, then removing that data would delete that copy of it. In that scenario, if Amazon later wanted to put the star ratings back into that bar, they would need to go and manually find that data to insert, or recreate it from scratch!

By employing separation of concerns, Amazon is able to update and extend their website whilst being able to sell millions of products across millions of pages and cross-referenced listings, and can do so without having inconsistencies from page-to-page.

This is not how lawyers tend to work…

Negotiations in legal transactions require lawyers to track and update multiple variables across each and every instance where those variables are described, e.g. parties, amounts, percentages, specific wording and so on. Until agreement is reached and the contracts are signed, these variables remain in constant flux. For the same reasons as described for Amazon, lawyers would — but do not — benefit from separation of concerns.

For instance, in a lending transaction the deal variables change through negotiation. If the amount of a loan is referenced on average x 5 times in each document across x 30 deal documents (e.g. the loan agreement, security agreements, corporate authorisation documents (borrower entity board and shareholder resolutions)) that’s 150 manual updates to be made, saved and redlined to check the changes each and any time that amount changes!

150 manual changes! Why is that?

That is because each reference to the loan value in each document is a separate copy of that data in multiple places, i.e. not linked to a centralised database of the deal’s key variables such as dates, amounts, percentages and so on. As such, there is no easy way to change that value once and automatically repeat that change across every reference in every document. The most lawyers can hope for is to do a simple find + replace in Word for a single document, and repeat that process for each and every other document where that value appears. And that takes time! A lot of time!

As we’ll see, Transaction Development puts lawyers in the same position as Amazon with regard to bulk updates to contract data. By separating the data (deal variables) from the presentation (the contracts in which those deal variables are described) it becomes easy and efficient to change the deal variables and have them reflected instantly across every instance in every contract where that value appears. Likewise, updating the presentation of the contract can be done without upsetting the underlying deal variables.

Why does the market need Transaction Development? What problem is it solving?

When I was a private equity M&A lawyer at Kirkland & Ellis, there’s a phrase I used to hear all the time from my colleagues, which was “Worst. Deal. Ever.” I heard it when I finished my first deal — rough, late nights digging through hundreds of pages of contracts making last-minute changes while “what’s the status?” emails pile up in my inbox. At the time I was relieved — if that was the worst, it could only get better, right? Wrong. The next deal was even worse, and the trend of “Worst. Deal. Ever.” continued. In the interest of self-preservation, I started to wonder why.

Eventually, I came to an obvious conclusion: it’s because deals like M&A and financings are constantly changing, getting faster and more complex, but we lawyers are scrambling to keep up, drafting documents the way they have been for centuries. It feels very unsustainable.

Today, partners and legal tech leaders at law firms I work with tell me:

“Sam, our team is strong, and we do great work, but I’m frustrated with all the document churn that gets in the way of getting deals done. Some of it, we can’t even bill to clients, and I’m sick of reviewing for missing zeroes and other stupid mistakes in the docs.”

On the client side, transaction counsel and deal teams tell me:

“Sam, I’m worried because I always feel a few days behind where the advisors are on my deals, despite the memos and catch-up calls. And I trust my lawyers, but when I catch a mistake in the docs, that trust evaporates, and now I’m frustrated because I have to check each one meticulously.”

On top of that, we know GCs are always under pressure to keep fees down.

It would seem like Document Automation should solve these problems, but it doesn’t, because deals are bespoke, and documents keep turning well beyond the first draft.

This is the conundrum that Transaction Development aims to solve: evolving our approach to developing transactions just as the transactions themselves evolve, helping lawyers and their clients develop complex deals with bespoke contracts efficiently.

How does it work? Can you give a use case?

For a concrete example and use cases, I can talk about Office & Dragons (O&D) and how some of our customers are using it.

O&D provides a termsheet-like command centre for creating and editing contracts, letting you simultaneously update multiple suites of documents, or automatically spin out new documents from previous work or templates.

When you’re working on a deal using O&D, rather than taking the deal terms (for example, financial amounts, closing date, governing law clause, etc.) and manually entering them directly in every document one by one, you put that information in just one place: a simple table (we call these “Turnsheets” because they are kind of like termsheets that turn into documents)). This forms the central data source — the data model — common across the desired number of contracts to a transaction.

Now, rather than hunting through dozens of documents for a piece of information, everyone knows exactly where to look and can find it quickly, without confusion. All relevant transaction variables live inside the Turnsheet.

Normally, making changes to any one of these terms is painful because you have to make conforming changes one-by-one across every affected document (on top of hunting through all of the documents to uncover which ones are affected). This process can take hours, even for something simple such as adding an additional zero to a financial figure that appears in multiple documents in multiple places.

With O&D, you make the change in just one place — the Turnsheet — and all relevant documents are updated at once.

In terms of use cases, one team that were among our earliest adopters was the aircraft finance practice of a large global law firm. When drafting the financing documents for a fleet of aircraft, they would typically negotiate and agree the financing documents for one aircraft, then reuse those documents for the rest. So, a lot of frantic copy/paste/trading of redlines between the lawyers on this team, their client, and opposing counsel. On top of that, last minute changes to the documents would often crop up, leading to major time crunches (and very late nights).

With O&D, they’ve changed their approach. They now negotiate and agree all of their documents with meaningful placeholders like [loan amount] for terms that might vary, instead of typing $100,000,000 directly into the docs, and separately agreeing to the Turnsheet which contains the specific data points. This has not only sped things up by removing a lot of toil from the process of spinning out and updating docs, but also by making the work easier to review and improving accuracy. Before, each side would check the other’s work by combing through redlines and sending markups where errors were inevitably caught, keeping people up late and delaying closing. Now, the documents are correct from the first send, so this process is no longer needed.

In other words, rather than needing to check each reference to each variable in each contract, you can check the Turnsheet and if anything is incorrect or in need of update, that edit can be made one time in the O&D Table and immediately updated across every instance in every document where that variable appears. This can mean tasks that previously took hours can be satisfied within a few minutes.

Importantly, you don’t need to know which terms will change in advance to use O&D. Since Transaction Development is a framework-based approach to automation, rather than a template-based approach, you don’t have to encode any fields at the outset. Instead, it’s highly flexible: you can easily add additional variables at any stage of the process and control these centrally via the Turnsheet.

At another firm, some members of the real estate finance team discovered a mistake in over 300 documents right before closing. They set up a Turnsheet such that it would replace the incorrect information with the correct information across all the docs, and one person fixed it in minutes, whereas before it would have been an all-hands exercise lasting hours. This deals with a pervasive issue in legal processes whereby inconsequential details — e.g. a simple typo — can, absent of a solution like O&D, have outsize negative impacts in terms of time, cost and stress to remediate. O&D resets the balance, making inconsequential errors inconsequential to solve.

What’s the difference between Transaction Development and Document Automation?

To explain the difference, I like to use the analogy of a factory.

In the olden days, when you wanted to build a part for something you were building, like a gear for an automobile engine, each of those parts would be made individually by a craftsperson, cutting parts one at a time. They could make any part they needed, but it wasn’t scalable. You weren’t going to put a car in every home. By analogy, that’s manual drafting in the legal world. It’s very flexible, you can draft any new or bespoke contract in the world, but it doesn’t scale — the next contract takes as long to draft or edit as the first one, and reviewing the document suite to ensure accuracy gets more difficult as the number of documents increases.

Moving forward in time, a major innovation in manufacturing was the introduction of plastic moulding machines. Before beginning production you need to decide exactly what you need to build and how. You invest a lot of time and money upfront building a big, expensive mould, but then you can crank out lots of parts very quickly and cheaply. It scales very well, but it’s not flexible, because the mould can crank out only one type of part. When you need a bespoke part or new product line that doesn’t fit the mould, you’re stuck. You either have to mould a similar part and do a lot of manual cutting and shaping afterwards, or else just make it manually from the start. And whilst this is happening, production may need to be paused.

That’s Document Automation.

It works where standard form contracts make sense, like an ordinary employment agreement. There’s not much value in bespoking those because there’s not a lot at risk or a lot of money on the table. They are also incredibly predictable from the outset, and therefore easily repeatable and not subject to much change.

LegalZoom has built a multi-billion-dollar business automating documents for these use cases. In law firms, however, there’s been very limited application, despite the fact it’s been around for decades.

When we ask lawyers and legal tech professionals why that is, they tell us “Our work is bespoke. We’re not just choosing between a few stock clauses in a standard form. Furthermore, we work on very tight deadlines. Spending a bunch of time making templates won’t help.”

So, they’re stuck with manual drafting.

Bringing the factory analogy forward to today, we’re currently witnessing the revolution of 3D printing. 3D printing changes the game, because it is a scalable way to craft any part with any customisation. Unlike plastic moulding, you don’t need to spend significant time and effort upfront changing the underlying machinery each time a new part is required. Instead, the thing you change is the data about the part to be made, which is sent to the 3D printer for printing. This makes it very easy, quick and cheap to alter production and respond to change. That’s how we see Transaction Development.

Transaction Development is 3D printing for deals.

Unlike document automation, which creates scalable but inflexible templates and requires significant prior knowledge of the automation subject, Transaction Development is about scalability and flexibility without the need for prior knowledge. It’s putting in place a framework that guides and supports the way deal terms are developed and contracts produced for any deal, even where all the contracts are new and bespoke.

Is anyone actually using Transaction Development today?

Yes! Office & Dragons is already being used by some of the world’s top law firms in practices like Finance, Corporate / M&A, Investment Funds, IP Transactions, Employment, and more.

Some of these firms have even found successful use cases in their litigation practices or for document processing functions like redactions.

We’re also having good conversations about Transaction Development with firms and other businesses who aren’t O&D customers. It’s not just about tech or our tech specifically — it’s a paradigm shift that leads to a better process for getting work done. Tech like ours can enable, empower, enforce, and scale that process, but a lot can be done even without tech.

Your company has a pretty unique name! What’s the story behind it?

Ah yes, the #1 question I get asked in interviews… Back when I was a lawyer working on the Worst. Deals. Ever., the office felt a lot like my dungeon, and I needed something magic like a dragon to save me… so yeah, it’s a Dungeons & Dragons pun!

Where can we go to find out more?

If you enjoyed this intro to Transaction Development, please check out our longer overview on Transaction Development. If you’re keen to know more about Office & Dragons and our implementation of Transaction Development, I recommend you check out this short video and our website. If you fancy joining the conversation please follow us on LinkedIn and Twitter and using #DraftDealsNotDocs.

Originally published at lawtomated.

We are the stories we tell ourselves. But what happens if one day that story changes unexpectedly? It causes trauma, but also change. Realising we have the power to shape our own narrative and not be defined by external notions of success is empowering.

This is the story of Olatunji “Tunji” Williams.

Tunji Williams’ career is a rich tapestry. He’s run political campaigns, been a Big Law M&A lawyer, founded a legaltech start-up, led growth at Litera, and today is co-founder of ShareThing, a social entrepreneur at the forefront of the fantastic buy nothing movement.

Tunji’s path is a heartfelt hymn to the fact careers are journeys rather than destinations. And like all journeys, there’s ups and downs, twists and turns, the unexpected and the serendipitous. We also touch upon the important interplay of cultural identity, imposter syndrome and how these push and pull on our ideas of success, access to experience and careers.

We applaud Tunji’s generous authenticity, and hope this interview inspires others!

Tunji, how did your career begin?

The funny thing is that you don’t just wake up one day and say “today, my career starts”.

I think when you look back, you actually realize, ‘Oh… my career started someplace else”, and it’s not when or where you would think.

So looking from the outside in, ostensibly my career begins at Hogan Lovells after law school in October, 2014.

That’s when I began my M&A practice.

I thought I wanted to learn how to become a world-class counselor to business titans and all that. That’s when I thought my career started.

But when I started thinking about this more recently, I realized that my career actually began when I was 19 years old — when I had the opportunity to manage my first political campaign.

How did you land that opportunity at such a young age?

I landed the opportunity by being naive and audacious!

I was a member of the young Democrats club in the town where I grew up and regularly attended the weekly meetings on Thursdays after school.

I would always look for opportunities to latch onto people, learn, and then use the learning to do something new. These were people that impressed me, that rose above the ordinary.

And one of the earlier meetings I attended, there was this guy there named, Calvin Ball. At the time he was the councilman for the 2nd district in Howard County, Maryland where I’m from.

I saw him speak, and I thought to myself, “wow, this is somebody I’d love to be like”.

So I asked him if I could intern for him over the summer. And he said, yes!

That summer interning for Calvin was my first career defining role, and I began to realize what actually gave me joy. It wasn’t money — I didn’t get any money at all doing that job despite working four days a week.

At the time I didn’t realise it, but I was learning what I love.

So that was the actual starting point for my career. It makes for an interesting dichotomy between the outside-in view, and what I’ve come to realize much later in life.

When you were 19 interning for Calvin Ball, what was it specifically that you figured in terms of broader and longer term career ambitions?

I wanted to be known for something. I didn’t want to disappear in history. I think I was, even at that age, driven by that. I saw that politicians seem to get a platform and leave their imprint on the world. So I thought I wanted to be a politician.

What I drew joy from the most was the constituent services part of politics.

I enjoyed writing to people, checking in on people who were struggling to pay their electricity bills, hearing people’s stories and realizing how similar I was to everybody around me and that I wasn’t quite alone and neither were they.

At the same time, I knew that others viewed this sort of thing as drudgery; the sort of thing you have to do at the start before you get to wear the suit and tie and be on TV.

What surprised me was how much joy I got from the constituent services work. It wasn’t the drudgery you’d expect, at least not for me.

Politics and law have a natural and easy overlap, and a lot of politicians have a legal background. Did having a start in politics inform a decision to go into law?

They were informed by one another. Absolutely. I was always going to go into law. That was my destiny. It was written.

I come from a family of barristers and attorneys going back several generations. It’s in the family, in the blood.

My grandmother was a barrister who trained in England and moved back to Lagos, Nigeria where she was chief magistrate.

Her father was an attorney. My dad actually took a different path and became a physician. But I always felt I was, I was headed that way — to law.

Stepping forward into your legal career in 2014, did anything change as you progressed down the lawyer track?

What changed is that I got scared shitless. Six months in, I was just scared. I was really scared because I looked around and I saw the level of perceived excellence, determination and grind. It was all around.

And I wasn’t sure I could maintain the mask long enough to get things I thought I wanted.

That scared me a lot.

It led me to start asking questions about my existence and my role in the organization and my curated life. I just… I just fell into this, this kind of malaise, because the more I thought about the business, the less I understood it.

How does the money actually move? Why are we getting paid this much to do this? How do the people on the other side of this know that I know enough to produce value? Who is quality checking this? Why am I the best person to do this? What do I do after I know how to do this?

The more questions I asked, the less I understood the path ahead of me. And that made me concerned.

I’m the kind of person that once I ask one question it leads to a second question, and on and on. I can’t stop.

And there wasn’t much room for that type of curiosity in the strict, kind of confined way we choose to practice law.

That’s what led me to look at other things.

And first, before I got brave, I experimented with other things. Other things meant trying to buck the traditional trend, and see if I could skip ahead and start bringing in clients and prove how valuable and smart I felt I needed to be.

For me this was a way to stop being scared.

That was going to be my story. In my head I wanted to be seen as the whiz kid rainmaker. So, I was looking for every opportunity to impress my boss at the time, David Gibbons, who is now global head of corporate at Hogan Lovells, and was a very senior partner even back then.

David also gave me my start — he was the guy responsible for interviewing me and giving me my job (and I’ll always be grateful to my fairy godmother, Randi Lewis, who set up the fateful meeting).

So one day I stir up the courage to walk down to see David, two doors down from my own office, and say “Hey David, there’s this company called FiscalNote, I want to tell you about…”.

FiscalNote was, and is, run by this guy named Tim Hwang, who I knew from Maryland political circles. At the time there was a glowing article about him in Bethesda Magazine asking if he’s the next Bill Gates, so I get in contact with him.

My suggestion to my boss at Hogan Lovells, David, was that we should represent this up and coming company pro bono. This was going to be big.

And David being, charitable and encouraging said, “go for it!”.

So I brought Tim in, I offered to take Tim to an Orioles baseball game, mimicking the partners I’d seen on TV and all the things I thought partners did. Tim, to his credit, politely declined the dog and pony show.

I, instead, invited him into the office and I walked him around, like a true rainmaker. I stopped by all the powerful partners’ offices on my floor and said, “this is Tim Hwang. He just inked a deal with JP Morgan, and there’s this article about him in the Bethesda Magazine, and his company is going to be huge etc”.

And they’re all just like, “great Tunji”.

What they didn’t tell me immediately — because they didn’t want to discourage me, is that, “you know, Tim can’t afford us yet”.

When I figured that out, it blew my mind. I couldn’t stop thinking: “He can’t afford us?”.

When you start to think about that deeply, it’s actually really backwards.

How can an entrepreneur who has proven fundamental value in the market and demonstrated the growth potential of a product, not afford world-class legal services?

There’s a fundamental and costly misalignment when an industry’s pricing model and standard mode of delivery are so rigid, as to prevent the top law firms from considering future growth potential in evaluating the suitability of accepting young companies as firm clients.

So that led me to think, “man, I gotta go face-to-face with this thing for myself. I can’t have anybody between me and real learning.”

I started talking more and more with Tim and told him, “look, man, I don’t know if this is the right time for us to represent you as an organization, but I want to be super-close in any way I can help. Just let me know”.

From then on, I couldn’t stop thinking about FiscalNote for months. I was telling everybody I knew about FiscalNote and introducing people to Tim, to the point where I thought “I’d be pretty good at FiscalNote, on the inside. Let me see if I can get a job there.”

And did you join FiscalNote?

Yeah. I went to go join FiscalNote, after being at Hogan Lovells for only seven months.

I was scared out of my comfort zone into this world of enterprise technology, which I knew nothing about at the time.

And I’d also gone from earning $160,000 per year to $39,000 a year, and in addition, having to travel an hour to work an hour back on the train every single day.

I started at the bottom. I was a business development representative and I was selling FiscalNote’s technology to law firms, including Am Law 100 law firms.

Just to pause there, for readers unfamiliar with FiscalNote, do you mind elaborating on the product and its use cases?

Sure. FiscalNote crunches data and produces predictive algorithms that analyse legislative and regulatory data. That analysis is used to score the probability that a piece of legislation or regulation will pass at different stages of the legislative or regulatory rulemaking process. In some cases we could do this with around 97.6% accuracy.

FiscalNote could drill down to the level of individual legislators and analyse the probability they would vote for, or against, the legislation in question. This would be helpful to any individual or organisation seeking to lobby and influence policy outcomes, i.e. you have a better sense of where to focus your political and financial resources.

They were also using tools like sentiment analysis during the rulemaking process to discern advance signals as to which way the regulators were leaning at a given point in the process, which could provide an edge to businesses or other policy makers and interested individuals.

I thought that was really cool. And for me, what it stood for was an opportunity to really democratize, and make better use, of public information, in order to help people and businesses make better decisions.

My personal thesis is that when everybody gets access to the same information, we see the best and the brightest rise to the top. We need to live in a world where that’s possible. Asymmetry of information is a powerful tool used to consolidate and concentrate power for the few. Open access to information is the antidote for the rest of us.

That’s a really interesting take. The printing press and the internet have successively reduced the cost of information sharing and thereby democratized access. The rise of MOOCs is amazing too — you can teach yourself a course taught by a leading university, often for free so long as you have a basic smart device and internet connection.

Do you see any caveats to making information more easily and widely available, especially where it can be used to inform decision-making?

Definitely. Information can set you free but can also entrap you.

Not all information is good information, let alone correct information. There’s also a need for wisdom. I think wisdom comes in different forms, but at its essence, it really is about having the understanding necessary to truly discern signal from noise.

And that can be gleaned via an algorithm, or the way it’s been done throughout human history — passing knowledge and wisdom down from one generation down to the next, through our families, tribes and broader communities.

Moving to Fiscal Note, that was a big move early on in your legal career. How did things pan out?

I’m going to be really honest with you throughout this whole thing, because I think that there might be wisdom in my story that I don’t even know about yet, that may help other people.

So I’m not going to sugar-coat it.

In general you need to be honest with yourself to understand yourself. The more you deny yourself, the further away you get from understanding and the further you get away from understanding, the further you get away from truth, and the further you get away from truth… well, it doesn’t end well!

So for me, when I was at FiscalNote, I was free in a way, because the future was unclear.

And I was looking for that at some level.

But my pride and my ego made me feel that I deserved something more. I had this narrative in my head that went something like this:

“I’m so smart. I had made it into Big Law. I made this decision to leave law. I’m so great. And I have a law degree from a great school. I shouldn’t be a sales rep. Are they kidding? How long am I going to be in this role? I’m ready to be a VP of something. I’m ready to be the big boss. I should be earning more than $39,000. I know the value of my labor and training etc.”

Those thoughts, those tracks, those scripts were holding me back from doing all the learning that I should have been doing.

So the learning I could have done in three months took me six months at FiscalNote because I had to move through those scripts.

I want to just step back and say that this is related to the same angst, that same script, I had while I was at Hogan Lovells. That script was telling me:

“$160,000 a year. You can’t be worth that much. They’re going to find out about you, man. Just stay inside the lines, shut up or do something different, so they don’t focus on the fact that you truly shouldn’t be earning that much money.”

It was a script about self-worth and proving my value.

Not only to others but to myself. It got in the way of me learning what I could have been learning while I was at FiscalNote.

I was focused on trying to understand my worth and my value, which is not a worthless pursuit. The irony is that you actually build real value in your life by allowing yourself to fully experience all that is right in front of you. That requires you to be genuinely present and mindful, and in so being, open yourself up to the hidden gems of wisdom, invisible to the undiscerning and distracted eye.

Whether or not you like the taste of that fruit, that experience, it nourishes your body. You learn more about what you like, what you don’t like, what you’re good at, and what you’re not. You need to learn this about yourself to move forward.

But in a nutshell, while I was at FiscalNote, I just got proud, man. That’s the honest truth.

And so I decided to go back to law. I wanted my fancy suits back. I wanted to do that type of work again. I wanted to be able to pay my loans that I’d been deferring — $350,000 worth, which are still pretty high because of the choices I’ve made.

So, I went back.

I went crawling back to David who was my guardian angel in many ways. I said “I think I learned what I had to learn”. I felt I’d screwed up, but really I hadn’t. But that’s what it felt like. I did, however, feel the business experience would make me more valuable as a lawyer.

But after I went back, I found the same thing again, the same script playing in my head. This time I lasted 11 months. I almost got there — to acceptance (or resignation, depending upon how you look at it), then I left again.

I‘ve quit my job six times since I graduated from college, I’ve been on a journey.

What led you to that decision point?

I hadn’t developed frameworks for life yet. I was still freestyling. And that freestyle-heavy life is like playing jazz.

Your soul kind of leads you to where you’re supposed to be. So it’s okay. But sometimes, you make a mess, and at other people’s expense. Even if the music you produce is beautiful, if you’re playing too loud and not in consideration of those around you, it’s hard for any tone to really groove with you, you know what I mean?

I didn’t have a framework, and I left because I was feeling uncomfortable.

And then, something else happened.

Back in 2015, there was an incident that happened in Baltimore, where I was living and working at the time.

A guy by the name of Freddie Gray was killed by the police in West Baltimore. And it caused massive unrest throughout the city. You know, people hurt and righteously enraged by what had happened to their neighbor, were seeking and delivering justice.

It was mesmerizing chaos in the city, and the whole time I felt more with the People, than I did with the people in my office. Not because the people in my office were wrong or bad. They weren’t. In fact,they held opinions just like mine about what was going on. They understood, they felt, they empathized, but they weren’t me. They weren’t my people.

Every day when I drove home from work, I felt like I was in the wrong place. I was missing. I was missing my life somewhere else. I was in somebody else’s body.

And it got to a point where honestly, I couldn’t leave my apartment for two weeks. I was in a deep depression. Really depressed for two weeks, my last two weeks at Hogan Lovells in December, late 2015.

So this is post-Freddie Gray, which happened a few months prior to that. But the city was still under the cloud of that tragedy. And I was just at this point where I was like, “I don’t know what’s next for me, but, I know this isn’t my life. And I don’t know what is my life. I just don’t know what to do.”

I was lost and very scared.

And so I called in sick, day after day, for two weeks straight. And I was on the floor in my fancy apartment, wearing the same clothes.

This was obviously a very rough and disorienting period for you.

Yeah, it was tough. As you can tell, it’s upsetting for me to speak about this period, but… I’m pleased that I’m on the other side of it, but it was… it was tough. It was worrisome. And I just knew that I had to be doing something else.

And this is where a friend of mine by the name of Reggie Fugett helps me out.

A lot of stuff happens like this in my life, where it’s just like, why me? Why now? You know, it’s not me. There’s something bigger than me at play here.

Reggie reaches out to me and he’s like, “Hey man, just wanted to check in and see what you’re up to?”.

And Reggie surprises me, he says, I’m thinking about running for city council in West Baltimore.”

So, we talked about it.

For context, we had been introduced four years earlier by a mutual friend while I was at college in New York. They’d said “you need to meet this guy, he’s the nephew of the first black man to ever build a billion dollar company in America, Reginald Lewis, and he’s from Baltimore, where you grew up. You should get to know one another.”

That’s how we initially connected and we had some conversations, but we never touched base again.

It’s kind of strange that we meet later again at this point in my life, and he’s like, “let’s meet up to discuss this campaign I’m about to launch.”

So we meet, have spaghetti and over dinner, and I decide to leave my job and run his campaign for a thousand dollars a month. Cheap date, I know.

Very soon after we went out in West Baltimore and we built the campaign from scratch. Just the two of us, out of Reggie’s childhood home. And from that, we quickly built the campaign to 150 plus volunteers.

We raised the most money that had ever been raised for a city council campaign in that district. Our campaign was also unusual for the fact that in a city with as rich and structured a political tradition as Baltimore, folks rarely enter the fold without asking permission.

You don’t just jump in (as we did), and try to win. Fortunately, we didn’t know any better.

How did the campaign go?

We came in second out of a field of seven candidates, and a very close second to the dedicated, long-time community organizer, Kris Burnett, who ultimately won the race.

The close loss notwithstanding, I felt truly at home during that process. I was with my people, even if I didn’t really know that part of Baltimore well yet. I learned a whole lot in that four months. I was back where I belonged, and that was grounding for me in the best way.

This sounds like an important and timely turning point for you?

It was. But I don’t want to mix issues here. I want to be really clear, maybe at risk of offending people. But my intent is good when I say that I wanted to be with my people.

By that I mean Black people. And I say that, not because I don’t have love for all people. I have immense love for all people. I do. And you can’t really love yourself if you don’t have love for all.

When I talk about black people, it’s worth me explaining how I grew up.

I’m from a country called Nigeria, a former British colony.

Very early, we’re taught how to hate ourselves. And love everything that was British and white, and see that as good and the path to success and esteem. Everything else that you are is to be hidden at all costs and that kind of suppression leads, I think, to collective neurosis.

It’s multi-generational and it infects the mind and the soul.

The difficult part about it is that ostensibly you may be doing well, really well perhaps; you’re progressing through society, as one is expected to do. And you might even be outperforming those that look like you.

But inside there’s a fundamental dissonance with respect to your identity.

Between what you are and what you think you need to be, or what others think you should be or stand for.

All humans experience that on some level.

But when you mix that with this complicated dynamic around racial and ethnic identity, it can become combustible, if not addressed. Left unattended to, the resulting trauma begins to manifest itself in one’s life in destructive ways.

I wanted to offer that in technicolor for the readers, for clarity’s sake..

My whole life I’ve existed in white spaces, where I was pretty much the only black person… forced to be a symbol for all that I represented to the people in control of those spaces. It’s tough. It’s tough on the young mind, because if you’re somebody like me, who likes people, and wants to please people you want to be for them, what they think you are.

It’s confusing and it’s a lot of noise and not much signal. So I was feeling mad at a spiritual level. When I left Hogan Lovells the second time. I needed to go wherever I could go unnoticed, somewhere I don’t need to be a symbol, so I could be closer to who I am.

That dissonance sounds very disorienting, and stress-inducing.

Definitely. This struggle is pervasive to anyone who doesn’t fit the standard profile of what society expects for this or that.

On this point, there’s a philosopher, René Girard, that wrote about the concept of mimetic desire.

This concept is nuanced and robust and there’s lots more to it, but it’s broadly about looking to projections of other people’s desires as a guide for what you want.

In Girard’s terms, that’s mimetic desire: a desire that’s derivative of somebody else’s desires and that you make your own. And it creates a duplicity of character that can become troubling to you over time.

He also talks about this adjacent concept of coming face to face with your idols. He explores what happens when you achieve the same level of knowledge and access to information as your ideals and what happens as a result?

He warns that you’ll want to fight them, literally or figuratively. It will create conflict in you. And that’s not what you really want; what you really want is understanding and self-actualization.

It’s part of growing up, I think, to try and get comfortable in your own skin and say, ‘this is how I am going to define my own success and what that means to me, and how I get there from where I am right now’… and not be too influenced by other people’s notions of what that is. There’s a lot of social, racial, class and familial pressures to do certain things in a certain way and in a certain order, or be limited in some way as to who gets to achieve what in life.

Speaking of which, you come from a long line of lawyers, and you mention it was ‘written’ that you’d become a lawyer.

Did that weigh heavily on you when you decided to leave the law for good?

Absolutely. There is this idea of identity. The stories we tell ourselves about who we really are.

If you read a certain bedtime story to yourself about yourself every night, and then one night when you’re 27, you decide to stop reading that story. What happens? It causes trauma.

You feel a sense of loss. You feel a sense of betrayal, to your origin, to your narrative. And it’s hard to get over that..

So yeah, that’s tough. It causes trauma, but I think once you have that realization it’s not so much about freeing yourself from a particular identity, as much as it is about recognizing that identities are created. Once you get there, to that epiphany, and unlock it can be incredibly liberating.

That’s a great way of putting it, the idea that we are the stories we tell ourselves. This realization must have been very impactful. How did it influence what you came next?

Well, those campaigns are a funny thing, because they only last a little bit.

And then you go back to real life and.. my real life was $0 in the bank account, $350,000 worth of debt still with interest accruing at various high rates and… no immediate job prospects.

There were folks that approached me, who liked the work that we did with the campaign and wanted me to maybe think about getting more involved in helping politically on other stuff.

But it wasn’t about getting ahead in politics for me, it was more that this experience had really built me up again as a person. That was bigger than an election to me. No next political gig could compare.

So I just reached out to this firm that I interned at when I was in law school called Miles & Stockbridge, and I pretty much just begged for a job.

I really liked the culture of the firm, which I do and did.

Luckily for me they took me on (thanks, again, to my Randi Lewis — my fairy godmother), and I was there for a year and a half. I have all the love in the world for that firm, and the people there. The lawyer, for my first company, and my current company — Venroy July, is an equity partner there. I’ll always be faithful to them. They’re a great team.

So you get back into being a lawyer at Miles & Stockbridge and reach a happier cadence, and then at some point you decide to start dealWIP, a deal flow management platform?

Right. I realize now that dealWIP was about something different than what I thought it was about at the time.

I’ll tell you what I thought it was about.

First, I was experiencing a lot of anxiety at work, like we all do. There was a delta between what people were expecting from me, and what I felt I could consistently deliver, irrespective of whether and what I actually did deliver, which 75% of the time was what they wanted.

Second, it was really tricky and stressful trying to keep track of everything coming at me each day, across so many different contexts, all seemingly at a million miles per hour.

Third, as wonderful as the people were at Miles and Stockbridge, if you work in law as a young black guy, there aren’t a lot of people that you can relate to, or people that feel that they can relate to you. People want you to win generally. I do impute that motive to most people, they want you to win; they recognise we don’t have enough black people succeeding, and we want this to do well, but they don’t know how to approach us. There’s worry about the risk of coming across as glib or condescending.

And I empathized with the seemingly powerful white people around me. They wanted to protect and push me forward, but didn’t know how, right? Of course, some people in life don’t want you around, let’s not gloss over that. So, bottom line, I felt like I was blowing in the wind sitting there, waiting for someone to save me.

I didn’t feel that I had anyone showing me the real blueprint for success — other than Venroy, who tried desperately (but I was too stubborn, and he was so busy trying to keep himself in the race — a 24/7/365 job for a black person trying to rise through the ranks in corporate law). I felt like I was getting the brochure all the time, from all angles. And you can’t really learn how to do something well with that, you can find the brochure bullshit on the internet.

What I needed was someone that was like, “you want a client? Here’s what you really need to do”.

So I started thinking, “how can I get access to that?”.

And how did you get to that knowledge and experience?

So, we moved to the States from the UK when I was 8. A lot of Nigerians have ties to the UK and I lived there with my Mum, Dad and brother until 1997.

That meant that as a family, we didn’t have a ton of lawyer contacts in the States that I could call up and say “hey, can I work at your firm? Tell me the partner to work for. Can you mentor me etc?”.

I just figured it out on my own. I was my own game tape.

What’s a game tape?

A game tape is when you record a performance — sports, music, anything really — and play it back to understand what worked well, or not so well, so you can optimize the former and minimize/mitigate the latter to improve.

What I wanted was to build my own game tape collection. This is what I did to get good at politics, and how I’m learning to be better in business.

It’s by analysing people I think are excellent at this or that, and then deconstructing why that is, and then initially mimicking those abilities and eventually making them my own. Finally adding my own flair. It’s part science, part art.

Got it. And how did you build up your legal game tape? And how does this relate to dealWIP?

OK. So I couldn’t figure out how to get game tape for the lawyers I saw really doing well.

For instance, just seeing their documents wasn’t enough. There’s no annotation, commentary or context. The stuff you really need to know to understand how and why they did what they did isn’t there. You also don’t have any easy way to record their calls or negotiations and figure out how they influence, persuade, manage clients or to dissect their bedside manner. How do you talk to the CEO in a way that inspires trust and quick confidence?

It’s all these little things, that in aggregate, make the difference between an OK lawyer and a great lawyer.

Sure you get some exposure to this each time you work with someone, but you might not always get to work with everyone, nor with the best people enough of the time.

You also need breadth and depth of these experiences. That requires seeing and understanding the full spectrum of all performers, to some extent. It’s hard to assess who is better at this or that without having some baseline against which to compare.

I started thinking the reason I can’t get access to all of that and further my learning and development, is that we don’t have integrated work systems.

I can’t tap into a matter and see every communication related to that matter, every phone call, email, every iteration of a negotiated document, everything.

And I wished I had that so that when I’m not getting work, and have some downtime, I can study top performers and make myself more objectively valuable to the organization.

The idea was to create that environment for that purpose, both to consolidate deal data into one single source of truth in general, but crucially, as a means for junior lawyers to level-up and gain access to those game tapes, to better themselves and learn from the best.

That makes sense. Having all the deal data, but as you say, crucially the context about why something was done a certain way, which leads into the what and how of the matter. If you only see the finished product, absent of context, you can’t always tell what is good, bad or mediocre legal work product. Some of the clause library tools we’ve seen fail on this, providing syntactically similar clause groupings but lacking any real context as to whether the clauses are buyer or seller friendly or highly context specific. Without that, you can’t learn effectively. You can’t know good from bad, nor importantly why each is which.

That’s right. It’s made worse by the fact that in law school, we’re taught to be direct-match learners, instead of first principle thinkers. You’re given a fact pattern, asked to find a legal precedent that is as close as possible to a direct match, and apply the precedent to solve a legal problem.

Rarely do you get into first principles in the true sense. You don’t enquire in the sense of asking “What’s going on here. What are the forces at play? What are the mixed incentive frameworks? Let’s analyze this at a really foundational level.”

I think the people that outperform the crowd, are first principles thinkers and not direct-match thinkers. It’s the difference between looking directly at the sun, and at starting the shadowy reflections in Plato’s allegory of the cave. I like to come face-to-face with the sun. It’s where I’m most comfortable. I prefer life outside the cave.

Having worked in politics and law, how did you find that transition to being an entrepreneur?

DealWIP was actually my second business. I started my first business, Stratosphere Records when I was 12 years old. My buddy and I, Powell Perng, had that company going through until 2003. That’s not on my LinkedIn. That’s too embarrassing!

That company was so much fun. We made a lot of music together, designed t-shirts, built a make-shift recording studio in Powell’s parents’ basement, and charged classmates to record with us. We even incorporated a company in Delaware. We did everything completely wrong, but we learnt a ton, and we had a blast. We were practicing how to create and build things from nothing.

With dealWIP, I left Miles & Stockbridge and raised a bit of money to build our prototype. I thought building software was going to be way cheaper and faster to build than it turned out to be. I’ve never made that faulty assumption again. I managed to raise additional funds, I think based on the confidence I conveyed to early investors and my vision about the future of the product and the industry.

The little success that we had, was as a result of the way we were thinking. I think our generous early investors thought, “this will lead to something good, even if it’s not this version of the company”.

Thinking back to what you said before about game tapes. Did learning from mentors to understand why and how they were successful at building that trust and quick confidence help you have those early conversations to win investment and build a team?

The answer is no, unfortunately. I never actually got that inside track training. Not because anybody was trying to deprive me of it, but more because the general dynamics at play when lawyering don’t foster too many of those opportunities to really understand why and how top performers are great.

But what I did get was an understanding of what convinces highly analytical people of your point: how to convince people, how to make a case, a strong argument and support it with substantive analysis.

That was what I learned; frameworks for reasoning.

Those were fundamental in helping me — as a first-time entrepreneur — to convince people quickly, and to the tune of hundreds of thousands of dollars.

Do you have any tips in that regard?

So number one, is to understand what’s important to the other person. Once you understand the other person’s operating system, you can make better assumptions, let’s say. You never make perfect assumptions because we’re human — we’re mired in our own bias.

But you can make better assumptions and you can ask the right questions. So, start there.

Number two, understand their mental models, their favorite mental models. How do they approach the world and think about the world? What are the biases that are most adjacent to their everyday logical thinking?

And from there, I can understand how they perceive facts, how they decide what’s most important, not just what they say is most important to them. People are often unreliable narrators in describing their own deepest motivations and triggers. And, if I see that there’s a mismatch in what they say is most important to them, and how they got to that conclusion, then sometimes there’s an arbitrage opportunity in a relationship, where you can help somebody get better results for themselves than they could’ve gotten independent of your input.

That’s how you demonstrate value. It can feel like a magic trick to the uninitiated. But, it’s really just about focused and intentional listening, and the bold, empathetic and genuine pursuit of understanding in each human interaction. I learned that framework from watching really good lawyers advise.

You’re right. The best sales people I’ve worked with, or had sell to me, have understood what you’ve just described. Sometimes 4 or 5 targeted questions into a sales conversation that person is able to laser in on a need, and that need is the nail they hang their pitch on and win over the prospect. The best make that invisible, natural and easy. It’s quite an art.

There’s an idea I heard recently on this point. It was from a leadership coach in Silicon Valley, that I listened to on a podcast called the Knowledge Project by Farnam Street.

He says that there’s a distinction between technique in social interactions, and behavior.

People can tell when you’re using a technique. It feels inauthentic. But when you practice a behavior that you’re using invariably in every single situation, it feels and looks consistent and true to who you are.

If you start asking lots of incisive questions out of nowhere, and it’s out of character, people will naturally be like, ‘hang on, Tunji doesn’t normally ask this many questions? What is he trying to get out of me? What’s his angle?”

Now if you adapt your behaviour and make that curiosity a genuine and natural part of who you are, and your everyday rhythm, not only does having those conversations become easier, but you will also be more successful when you have them.

It will be easier for you to understand people and their drivers better without it being weird.

That’s very true. As a buyer of legaltech, and running this site, we get sold a lot of products. It’s noticeable when someone has learnt a technique but not yet mastered the performance if that makes sense? Using people’s names — as suggested in Dale Carnegie’s How to Win Friends and Influence People — is a good example. It’s a powerful social skill when used effectively, but selectively. Too often people misunderstand that tip and overuse names to the point it sounds totally unnatural and, to be frank just plain weird.

Absolutely. Technique versus behavior is about integration. And like any good integration, it needs to be seamless, natural and ideally invisible.

Technique is something you do. That’s something separate from yourself. Behavior is who you are, right?

What you think becomes what you say, what you say becomes what you do. And when what you do becomes who you are. It becomes behaviour.

It’s easy to say, but tough to understand.

Technology is like that. It’s best when it’s invisible, when it flies by you and you don’t even notice it. On that point, returning to tech for a moment, you built a tech start-up from the ground up and ran it for several years. What happened next and why?

Over the course of those two years or so, we raised nearly a million dollars to build up a team and a product.

We’d seen reasonable growth. But as you know, it takes 18 months minimum to land the big law firm sale. Even at Litera — which we’ll get to later — that has such an entrenched sales channel, it’s still a 12 month process.

For start-ups as small as we were, you aren’t necessarily well positioned to do well in that contest, unless your offering is so differentiated that the customer, or the market in general, is willing to compress the sales cycle.

It takes a little bit of naïveté to believe that by will and power of personality, you’ll be able to alter that dynamic. And naïveté is exactly what we had.

We were encouraged by having gotten into the Lexis Nexis accelerator and MDR Lab. We felt that maybe there was something fundamentally valuable about the way we were doing this, or perhaps our brand or message that resonated with people.

That encouraged us to keep on going. Even if the product wasn’t coming together as quickly as we would’ve liked, a lot happened over those two years.

We pivoted slightly with the product direction, narrowed our scope in response to the feedback we got spending three months at MDR Lab in London. That was when our hardcore development happened, helped along by being there with the people who would use it everyday, and getting out of our own assumptions and our definition of the identity of the product and moving instead into a user-led understanding of what they needed and wanted from us.

That was beautiful and edifying. Humbling, too.

But at the end of the day, we didn’t have enough revenue or enough customers to convince the market that we were ready for a seed round in the two to three million dollar range.

I could not find anybody to invest at that level in time to keep the company alive.

Selling to legal organisations is tough. Lawyers are hard buyers. They’re perfectionist, sometimes pernickety, and quite all or nothing in their buying mentality. Even if a product is amazing, and far better than the cost of doing nothing, sometimes a sales cycle can fall apart for very trivial reasons such as the product’s workflow not matching 100% the exact way of working the users at that particular firm in that particular team do their work, even if overall it is 95% a fit for them and all others in their niche. And that decision might come at the end of an 18 month sales cycle.

And as you say, that holds true for the big players like Litera, who you joined after dealWIP wound down.

How did that move come about? What transferable skills did you carry across from your prior experiences into the Litera role?

I was really blessed, first of all, to get that opportunity.

I missed ILTA that year. It would have been embarrassing to show up knowing that we were going through that process at dealWIP. We had to let go of five employees in our office in Nashville, let all of our contractors go, and my co-founders returned back to work.

And one of my best friends (Zach Croft) sadly passed away tragically during the same stretch. It was a period of real darkness for me.

Out of the blue I get a call from Noah Waisberg, CEO and co-founder of Kira, who’s at ILTA and he says, “You know Tunji, you should talk to Avaneesh at Litera. There might be a good match there.”

So, that’s what I did. Everyone knows Noah sees around corners. And, everybody that knows Avaneesh Marwaha knows that he’s one of the most casual and down to earth people around. He’s not what you think you’re getting with a private equity-backed CEO. When he jumps on the line, he’s like, “Hey, what’s up?”.

He calls me up and I thought, “this is going to be OK, I can talk to this guy”.

Before the call I was afraid because I thought everything hinged on it. I thought this would be our chance to sell dealWIP and get something out of it for our investors and that weighed heavily on me, in terms of coming to terms with the heaviness of the nearly million dollars we’d been entrusted.

We started talking about how due diligence project management — what we’d built dealWIP around to that point — was an obvious on ramp to transaction management technology, of the sort for which Litera is now well-known. Things started to make a lot of sense, we could see what each other were doing, we continued talking and I started speaking with the Chief Product Office at Litera, Jason Vander Meer, and vibing… and I thought “wow, we’re going to get sold after all”.

But long story short, it didn’t work out that way.

The deal just didn’t make sense for Litera at the time. And having been inside the company now, I completely get it. They were integrating Workshare Transact and Doxly, which was the focus, and was a behemoth of an effort in and of itself.

And that is when Haley Altman, founder of Doxly, which was by then a part of Litera, asked to grab coffee in New York to catch up and chat about whatever I was planning to do next.

So, we sat down and broke bread.

Anybody that knows Haley knows that she’s a force of nature. She’s really good. She has singular focus. So when she described what she was after in her new role, it jived with my ambitions and vision, and I saw a role for myself and she asked me to join and head up strategy for the Transaction Management product line at Litera.

And I thought, “are you kidding me? I get to do the same thing I was doing at dealWIP, but with access to unlimited capital. Yeah. I’ll, I’ll take that!”

It was very fortuitous. I got to work remotely as well, so that was great because my wife and I got to move back home to Maryland from Brooklyn, which was when we also learned we were having our first child.

It was just perfect timing; returning home, having a job that was flexible with access to capital and starting a family. It was just an answer to prayers.

Right place, right time and right network?

Absolutely. I’d also like to highlight Avaneesh, and of course Noah and Haley, who extended me a timely opportunity. They each saw what I’d done and what I wanted to achieve, and found a way to put me in position to shoot my shot. From there, it’s all about wanting the ball. And, I always want the ball. I love to shoot.

Network is so important. It’s a lot easier to build a strong network if you are genuinely excited by the domain. One thing we’ve found about the legaltech market is that networking seems very easygoing, natural and supportive. For the most part people are very open and authentic about sharing their war stories as well as their successes. It doesn’t feel forced as say legal or finance networking events where it’s perhaps less like that on average.

That’s right, I think. It’s great to not need a happy hour and a bunch of drinks to drop the corporate mask and be real and admit that you don’t really want to talk about the nuts and bolts of a rather dry legal or legaltech topic, but instead want to get to know the person and what made them happy or hurt them that day.

We’ve covered a lot already but what tips would you recommend to people, at any stage in their career, thinking of embarking on a change, whether it’s from law into politics, tech or starting a business?

Number one is this, and I’m fretful about saying this because I don’t want to come across in the wrong way, and lose people. But in all earnestness, and it will mean different things to people: talk to God. Talk to your God, whatever or whomever that is. God is real.

For me that means going inward, slowing down, and really thinking about what moves me. Don’t be a thermometer, arbitrarily adjusted by others’ energy. Try to be a thermostat if you can, intentionally adapting to what truly moves you rather than letting other people’s notions of success drag you this way and that. And, the only way you can do that is to understand the power of heat. If you don’t understand heat, you can’t take control of the temperature.

Number two, seek wisdom. But be careful to whom you talk. Because not everyone knows what they’re talking about! And not everyone necessarily wants for you, what you want for yourself.

Number three, develop a disciplined and structured way of evaluating your go-forward path. And what that means to me, is allowing yourself to freestyle. Play your jazz chords, but also understand the mathematical rigor with which traditional orchestral arrangements are constructed. Blend those two worlds artfully, and one can produce real magic in the world.

In more concrete terms, that means systematically de-risking your opportunities.

Try to understand your invisible assumptions and try to validate those first before making a move that will put you at unnecessary risk or have an adverse impact on those around you. Don’t take risks just to take them because it feels good. Try to do it in a responsible and sustainable way.

Number four: be honest about the outcome of your experiments. Don’t tie yourself too closely to any idea. Your idea, your experiment doesn’t have to win. You don’t have to be the CEO. You don’t have to be a lawyer. You are because you are, and your results are what they are. Separating your results from your identity allows you to play with lots of things, because they’re just things — they aren’t you. Your legal education is a thing. Your career at any given point is a thing. But it doesn’t define your identity. Play with those things to make your life fruitful and make it interesting, try to learn and to bring other people close to you because that’s where we find joy.

The last thing is to seek truth. Once you honestly set your mind on seeking truth, even if the truth ends up being different than your ideas or what you perceive to be your identity or the value-set native to your tribe or your people, it sets you free and gives you the kind of peace and insight that will surpass or evade common understanding. In that, there is tangible opportunity — concrete commercial opportunity, but also spiritual freedom.

And I want to be clear here.

Seeking truth, and being true to yourself, are two different things.

Talking to your God allows you to be true to yourself. Your God knows who you are.

Seeking truth is outside of yourself, because what is true for you is not necessarily true for your neighbor. So when I seek truth, in a sense I’m looking for what’s most true or most relevantly true in a given moment.

For example, if you tell me that I make you feel awful and if I am saying to you, my God tells me that the way I treat you is the way I’m supposed to treat you, there’s some dissonance there that’s going to cause you suffering and also cause me suffering.

In that scenario, the truth I need to seek in the moment is what you are telling me, because if my intent is good, is to live in harmony with my neighbor and the people around me, the most relevant truth at that point is how I’m making you feel. And that requires humility, character and discipline. It requires you to quiet your ego and look for what matters.

You are now the co-founder of ShareThing. Appreciate this is a very recent venture, but is there anything you can share?

Let’s not spend too much time on that because that’s very new, and I don’t want to tell a story before it unfolds.

What I can say is that the love, the trust, the truth, the growth, and not worrying so much about things, and worrying instead about the people, is where ShareThing is coming from.

It’s this idea that what’s more important than anything are the meaningful connections between humans and not so much the material things that we’ve come to worship, whether that’s our careers or our cars, or our third monitors (lawyers know what I mean).

Those things are only good in so much as they bring us closer to realizing that we are really connected to one another in a deeper way than we could even imagine.

That’s the cool thing about ShareThing. It’s based and built off something that pre-existed me. It’s a genius idea that I had nothing to do with, the buy nothing project. There’s lots of literature out there on what that is (see here).

It’s a beautiful concept. Unincorporated free flowing organization, more of a movement. It’s about creating distributed hyper-local gift economies in which the true wealth is the web of connections formed between people who are real-life neighbors, who share.

There are already 3 million people involved globally, spanning 44 countries. The movement has over 6,000 hyperlocal sharing groups, and is growing at nearly 230 groups a month. In January 2021, the movement trained the most people ever trained in a month to be administrators or host these groups. Before January 2021, the previous record was 250 people trained, and in January 2021 the movement trained just under 2000 new daily volunteers.

We’re seeing this inflection point globally, and the size (and rate of growth) of this movement is awe-inspiring. We think it’s the right time to build a social sharing platform. We see really heavyweight competitors going into this space and trying to gain ground.

Facebook is beta testing a Neighborhoods feature, which is based around ostensibly similar ideas. It’s something they want to make core to their platform later this year. They’re testing that in Canada right now — a country where the Buy Nothing Project has a large and rapidly-growing community foothold.

Another company, called Nextdoor, is currently valued at $2.2 billion and may shortly go public and aim for a valuation of $5 billion this year. They have 27 million users. It gives you a sense of the value of the Buy Nothing Project community — already at 3 million users, with zero marketing.

And then you also have Amazon Neighbours, another similar initiative.

But no one in the space has as strong and trusted a brand as the Buy Nothing Project. It’s a beautiful opportunity that comes with immense responsibility. My co-founders and I have to steward and protect the integrity of the community and the brand. It’s way more important than money. It’s too important, to too many people, to squander. We’ve committed ourselves to building this business thoughtfully and with conviction, at every stage. We’re dancing to a different tune with ShareThing.

It’s all part of this emerging idea of connecting with people where you live that’s about to take flight, and we happen to be in the right place at the right time and want to build a brand with integrity around bringing people together in meaningful ways in the physical world.

So many of the material possessions we all stash away in our homes essentially function as options on things that we might enjoy one day, sometime in the future, or maybe never. Those are potentially valuable things somebody else could enjoy right now, in the present. We should be moving these things around, sharing them via our personal and community networks. It’s a beautiful idea. We have the technology to make it a global reality, in every corner of the world. That’s what we’re doing at ShareThing. It’s a massive undertaking. A very long-term journey.

That sounds really apt. Especially as everyone has had to pull together more in the recent tough times we find ourselves in with a global pandemic. That and other headwinds such as environmental concerns seem to be driving more neighbourly connections.

Lastly, do you recommend any books, podcasts, blogs or social media to check out, things you’ve found helpful to your career and life decisions?

I’d definitely recommend:

• The Knowledge Project podcast by Farnam Street. This is a great podcast about better thinking, problem solving, and decision making. I’ve learned so many great insights about how to think better from this podcast. Well worth your time.
• Venture Deals: Be Smarter than Your Lawyer and Venture Capitalist by Brad Feld. A must-read for anybody trying to start a business and negotiate with sharks!
• The Lean Product Playbook by Dan Olsen. This is a great resource on lean product development. I learnt everything I know about product from this book. It aims to bridge the gap between The Lean Start-up and how those principles apply directly to building great products. It walks you through a lot of practical examples and a repeatable, easy-to-follow methodology for iterating your way to product-market fit.
• The Buy Nothing, Get Everything Plan by my ShareThing co-founders, Liesl Clark and Rebecca Rockefeller. It documents their journey from 2013, when Liesl and Rebecca launched the first Facebook Buy Nothing Project group in their small town off the coast of Seattle, which unexpectedly became a viral sensation. It’s a great read on discovering the joy of spending less and sharing more and living generously. Very inspiring.
• The Revolt of the Public and the Crisis of Authority in the New Millennium by Martin Gurri. This is a great read about how technology has reversed the information balance of power between the public and the elites who manage government, political parties, and the media. In doing so, Revolt of the Public tells the story of how insurgencies, enabled by digital devices and a vast information sphere, have mobilized millions of ordinary people around the world to challenge the status quo.

Finally, I have launched www.tunjiwilliams.com, a personal project to explore many of the themes that came up in our discussion through various of expression: visual art, photography, original music composition, poetry, etc. I hope you enjoy it!

⚡ Interested in legaltech careers like Tunji’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

What do you get when you combine elite sports and a history of working in-house for various tech start-ups and scale-ups?

Tom Dunlop.

Tom is a former Team GB badminton player, in-house counsel, and now CEO and founder of Summize; a platform that creates instant contract summaries and assists users throughout the contract lifecycle.

It’s no surprise that Tom brings a fresh and unique perspective on legal, tech, business and life.

His guiding focus is Kaizen, the Japanese philosophy of continuous improvement — consistently improving something every day, little by little.

For Tom, if you want to achieve anything, it’s about going the extra mile and looking for small wins made every day that add up to big gains at the year end. It’s how Tom trained as a sportsperson, how he thinks about his own personal development and now how he runs Summize.

Where did your career begin? How did you find yourself in legaltech?

My start was unconventional. From my teens into my early twenties I was juggling professional level sports and studying. No easy task.

I was waking up early to train before school, and later university, while touring and competing around the world.

Towards the end of my law degree, I needed to choose between professional sports and law. Leading a double life meant increased demands. In the end, something had to give, and I chose to pursue a legal career.

What was your first career break?

My first foray into business was actually in law school. I founded an online comparison site, comparelegalsolutions.

It was the first solicitor comparison website on the internet, comparing solicitors by price, distance from the consumer, and quality.

It was reasonably successful, especially considering I was still juggling my degree and sporting career at this point.

Some of the early feedback I received when applying for training contracts was that I needed to develop my commercial awareness and experience. This was despite building a professional sports career, which included all of the commercial aspects that come with that.

So, rather than focusing on the usual things, I thought I’d try and start a business, which I was already — even at that stage of my career — thinking about for the long-term.

How did it pan out?

The site received a lot of buzz initially; we signed up a number of firms and garnered quite a bit of press coverage.

Together this paid off the development costs and we made a good run of it for a few years.

But then I landed my first legal job.

Again, it was a bit unusual. I joined a start-up law firm, Prosperity Law LLP, founded by an experienced lawyer who had been Legal Director for a variety of companies, including those in the British nuclear sector.

I was very lucky. Prosperity was set up as a law firm and sports agency at the time. It was a chance to combine my interests and experiences in sport with my legal background.

The other great thing was that it was very commercial and perhaps less typical for an entry level legal role.

What sorts of unconventional things did the role entail?

Aside from legal work, I got some great hands-on experience advising and assisting the management and strategy of Prosperity International Sports Management, which included finding new talent.

I worked on the contractual negotiations and sponsorship opportunities, and helped recruit Olympic athletes and footballers, including players at Premier League clubs and a number of ‘introducers’ to increase overall turnover.

That sounds like the perfect fit?

It definitely was at the time. It was an unusual route into becoming a trainee solicitor. But it was really fun learning the ropes within a business that was part law firm and part sports agency.

We also worked with a number of really interesting and large legal clients. Big clients like Metrolink, Manchester’s light rail system, and Palmer & Harvey.

I got to merge my legal, commercial and sports interests on the job, and had flexibility to keep up with my training and competitions around work.

It was important to me that I had a balanced career that didn’t shortchange my passion for sports.

Would you encourage law students to seek out these more diverse career opportunities?

Definitely. I’d encourage students to think outside the box when it comes to legal careers. Working in a huge law firm isn’t everything.

Sometimes smaller businesses can be a great way to quickly level up and take on exciting growth opportunities, which in larger organisations might have been deferred until much later.

With a bit of luck, a lot of grit and the right opportunities, you can find some surprising overlaps between your interests and your legal and commercial skills.

It’s not easy, but it’s worth it.

Did qualification as a lawyer change things or give you a new perspective?

Yes it did. In many ways it was a culmination of different thoughts I’d been having.

Having worked so closely with some impressive and interesting clients, I decided I wanted to do more of that, and felt moving in-house would enable me to do so. I really liked the variety and closeness to the businesses we worked with and wanted more of that in my career.

So I made the jump, and my first in-house role was at Speed Medical. However, it was becoming Head of Legal at AppSense a few years later that pulled me back into tech.

AppSense is also where I laid a lot of the foundations for Summize.

This sounds like another turning point?

It was. AppSense was a fast growth tech company with a global presence. They’d already hit $90 million in annual revenue by the time I joined.

I was only one year qualified so it was a big opportunity for me to establish and push the legal function from a standing start and really cut my teeth as an in-house lawyer.

AppSense is also hyper relevant to what I do now. It’s where I met my Summize co-founder and CDO, Dave Smith. It’s also where we met our Chairman and investor — who is the owner of AppSense — as well as our CFO.

Aside from the founding talent, is this also where the use cases for Summize originate?

Absolutely.

At AppSense I was managing a large volume of contracts. I was creating, reviewing, and tracking them all day, every day and helping our business action and make sense of them.

We were looking at contracts from all angles, including diligence-type tasks such as red flag reviews, and had to create actionable summaries for contract lifecycle management purposes. We also had project-based and macro event-driven reviews.

All of this combined meant I had to review and action a wide variety of contracts and contract related use cases. Being a lean team and working so closely with the business, I got great exposure to the wider personas that work with contracts, which I found particularly helpful.

Given my interests in tech, and the fact that AppSense is a tech company, I was always hunting for ways to improve our process, standardize it and, if possible, use tech to automate or augment where appropriate.

I needed to scale legal as quickly and as robustly as possible while the wider business was growing.

This is really when I started to get interested in legaltech, and I would continually think about ways in which I could make the life of a GC — including my own — easier and more effective.

After the acquisition of AppSense by another company, I fancied a change and wanted to get back into another fast growth, early-stage business.

That led me to join Zuto, a car finance platform, and then later UserZoom, a platform used to plan, design and measure customer and user experience.

Why did I start a business? I think it’s a combination of the fact that I was both a potential user and also working with other users who needed to understand contracts for different business purposes. It was very inspiring working in fast-growth environments, scaling businesses and processes, both internally and with the products each business sold.

Eventually I caught the bug. You start to think… why can’t I have a go at this?

Between working at AppSense and Zuto, I’d been gradually scaling up my efforts to design and build Summize with a small team of AppSense alumni.

A bit like with sports and law, I then had to decide between two paths; carry on in-house or take a run at launching a business of my own.

What was the final tipping point, after which you decided to launch into Summize full time?

Interest and investment. We’d built prototypes of Summize and had iterated a lot of customer feedback — we were getting a lot of early buy-in. Very quickly we then started signing up users.

We went for investment, which we got, and that’s when it was time to push the button.

As we won investments and had customers lining up, we thought we needed to make a go of it, and grow a team. You can’t do that part-time.

How did your employer feel about the decision to leave and launch Summize?

I was always very open about the fact that I had this start-up that I was running on the side.

I’d also say I was actively encouraged. My employer loved having people working for them that were going to be future founders. They always had an encouraging approach — so long as you did your work and your side project didn’t detract from that, then it was no problem.

They were very helpful and encouraged me and my budding Summize team to ask questions, learn from colleagues and understand generally how to emulate what they had built in terms of starting and scaling a fast growing company.

There’s a number of lawyers who built businesses on the side around their day jobs and ultimately quit to make a go of it. Often they weren’t especially encouraged to do so, and in a few cases, quite limited in what they were allowed to do. Do you think law firms are missing a trick if they take a heavy hand to such entrepreneurial interests?

I do think it’s a risk. Obviously you don’t want lawyers who will be distracted from their work, or who will risk the reputation of the firm.

But law firms should take a keen interest in helping entrepreneurs who might later become a client. All the more so if the product they are building is something the law firm would derive value from, or could sell to clients.

One person who famously talks about the idea of hiring future founders is Peter Thiel, also a former lawyer (Sullivan & Cromwell). He was one of the founding members of PayPal and later an early investor in several unicorns, such as Facebook. Peter and the other founding members of PayPal, are today known as the PayPal Mafia for the fact that they’ve all gone on to found one or more unicorns.

As a result, Peter Thiel talks a lot about intentionally hiring people into their last job, i.e. the last one before they go and found their own company. I think this is a great strategy.

What it means is that you hire people who are hungry and eager to learn and grow fast, and they take on greater responsibility and push boundaries.

If they then decide to leave and start their own business, you will undoubtedly have benefitted from a super-driven employee and potentially created a valuable node in your network.

We encourage the same at Summize. For example, one of our marketing team is currently building a successful clothing business via social media on the side. We love this creativity, and the entrepreneurial zest to find ways to grow and do things better.

If you can borrow these people before they go on to start their own business full time, it’s great.

Did your earlier experience working in tech companies influence how you think about Summize?

100%. Working in companies that promote innovation changes the way you think as a lawyer, and as a business person.

The idea of Kaizen sounds a little daunting but it’s really great. Everyone constantly looks for little ways to improve the business and every process. It’s a nice way to get everyone pulling together.

This has helped me and the Summize team find gaps in the market for contract tech.

Don’t get me wrong, there’s a ton of great vendors in the contract space. But we found a number of gaps in existing tech that we wanted to work with. Some of those gaps aren’t particularly tech related, but are more focused around customer experience.

There weren’t a huge number of tools that were super simple, easy-to-use, lightweight and cost-effective. That’s where we fit in.

Tell us about Summize. What problems does it solve and for whom?

We were founded in 2018 but didn’t officially launch with the current team until 2020.

The original idea focused around summarizing contracts for various business and legal purposes, most of which were inspired by my experiences and use cases as a GC.

What we offer today is a lightweight assistant for the contract lifecycle.

Summize is about supplementing not supplanting lawyer work. Our focus is on tackling marginal gains around typical legal tasks relating to contracts, and also similar contract related tasks relevant to other business users.

Our target clients are both law firms and in-house legal teams, and business users working with contracts on a day to day basis.

Are there any specific features you’d highlight?

We break down our use cases into pre and post-signature tasks.

For pre-signature, we provide a Microsoft Word Add-In, which allows users to quickly understand and navigate through key clauses. Key features include identification of defined terms throughout the contract and tight integration into our web platform.

Summize instantly creates a summary of any uploaded contract, no matter how unique. Those summaries can be edited and shared, and users can add comments and red flags.

Post-signature contracts make use of our web app. The web app provides a lightweight and easy-to-use contract management system, alongside quick and powerful contract summaries.

Like a lot of start-ups we’ve evolved our focus.

Originally we focused on due diligence and volume work, but have since zeroed in on being a lightweight, easy-to-use and easy to buy platform. Users can pick and choose each modular aspect of the product and slot it into their existing workflows where they see fit.

We’ve really tried to make the ‘try and buy process’ as frictionless as possible. That’s why users can sign-up for a free trial via our website.

It’s always better to let users try a product and see for themselves if it solves their need, rather than try and box them into a buying with endless demos and slideware.

Based on your experiences as an in-house counsel and as a founder, do you think the most impactful opportunity to transform legal is either big disruptive innovations or marginal gains driven by continuous improvement?

The latter. Transforming legal processes for the better, mostly involves standardising workflows and finding ways to add subtle automations or augmentations to the lawyer experience.

Most importantly, we need to work where the lawyers are already working and make the changes there.

Right now, legal is in a halfway house between being wedded to Microsoft Word and having an openness to exploring other contract editing platforms.

To meet lawyers where they already work, we’ve focused on making integrations to the systems they — and their clients — use everyday. That includes: a web app, a mobile app, a Word Add-In and integrations with Microsoft Teams.

As part of our customer on-boarding process, we adopt the Kaizen mentality. We help clients look for small improvements that they can stack up to create larger gains over time.

We suggest that the first thing they do is download the Microsoft Word Add-In to supercharge what they already do.

Why is that important for you and your customers?

For one thing, it lowers the change management overhead. Helping users get better at working where they already work is easier than trying to persuade users to adopt something entirely alien and unlike their existing or previous ways of working.

We are making it easier for lawyers and their business colleagues to collaborate. The latter don’t want to be dragged away to some lawyer specific platform that they only ever use when interfacing with lawyers — that’s literally the last thing they want to do.

Working with lawyers should be seamless and easy, not some process or system entirely removed from the way the wider business functions.

How do you see Microsoft 365 (formerly Office 365) impacting legaltech?

I don’t think that the future is some big, all-encompassing legal platform.

For one thing, the clients of lawyers — whether internal or external — won’t want to use some end-to-end legal platform for their day to day tasks, including those that interface with legal.

Instead they use Microsoft for the most part, or perhaps Google workspaces.

If you can build a product into the existing legal-business workflow that is already happening in and around Microsoft Teams, which can automate the manual processes and link together disparate data, you’ve probably increased your adoption significantly.

That is how the future of legal services evolves. The change will be around enhanced use of the tools users already have, not some paradigm shift to a legal specific omni platform that drags users away from their day-to-day tools.

Ultimately legal has to cater for the client, and the clients are all going over to that way of working.

What is the risk of ignoring this trend?

The more legal tries to create separate ecosystems, products and platforms away from where the business works, the more likely that it will alienate the end customer — the business users that buy legal services.

How, if at all, did having a professional sports career influence your business career?

It’s been hugely valuable.

The only difference between the top athletes is their mentality. Above a certain level, physical skill is no longer a predictor for success.

Of course there are the Ronaldos or the Messis of the world, but even then, they are only just a bit better physically than the next best player. What really sets them apart is their mental game. And that undoubtedly contributes to their physical game, whether it’s their confidence or drive to go the extra mile in training.

At one time, I was the European №1 Badminton player. During that time, I developed this sense of inevitability that I would win everytime I walked onto a court.

The way that I developed that was by training at 04:30am every morning. When I was training I knew that my competitors were asleep.

Sure, they were able to train more than me overall, but I took a lot of energy from the fact I was getting up super early to train, and I juggled more than they were juggling. And this grit and drive carried through into my career.

It used to frustrate me — and still does — when you see people who do the bare minimum, who aren’t obsessed with improvement and doing the best they can. Having the right mental game to commit and deliver each day on your goals builds your confidence and, in sports, your physical competence.

How do you apply some of these experiences and ideas to Summize?

We adopt the same ethos internally. However, we don’t expect everyone to be up at 4:30am!

One thing we do is to hold a meeting at five o’clock on a Friday called “1% better”. We know that every other team is probably clocking off for the week, happy with their performance… and in pre-covid times, perhaps down the pub.

Instead we are strategizing about how we can get 1% better next week.

We try to obsess over this.

We look into all the data we have about our processes and tweak tiny actionable things, measuring their impact: good, bad or indifferent to the overall process. Things that work, get repeated. Things that fail are removed.

As I say, it’s making consistent commitments to small, actionable changes each day and sticking with those that add value and removing those that detract value.

This is how you win in sport, and how you succeed in business.

Do you think the legal industry struggles with these sorts of ideas, such as Kaizen and marginal gains?

Yes, I think the biggest problem people have is that they’re looking for the silver bullets — the huge wins and instant fixes.

There’s almost this sense — said or unsaid — that there is some magic solution out there that dramatically, with little to no effort, transforms the legal function.

Weirdly there is also an ‘all or nothing’ mentality that is inherently conflicted. If tech X doesn’t entirely automate my job it’s no use, but at the same time, please don’t automate my job.

It’s an odd one.

What advice would you give to anyone thinking of entering the legal tech startup space from a legal background?

The first thing is to get into the mindset of just being creative day-to-day.

If you are a creative person and can look at a process, map it out, suggest improvements and involve yourself in a project, you will start learning the necessary skills to work in and around legaltech.

If you do a good job, those projects will start to find you as you become more experienced and knowledgeable.

Contributing to blogs, attending conferences, staying up to the date with the latest technology and volunteering to support legaltech companies can be great ways to gain the right experience.

If you keep your finger on the pulse, have an opinion and build that experience you will start to build connections.

Now is a great time to do that. A lot of legaltech businesses are still small enough where you can, if you ask in the right way and with enough persistence, open up connections and a knowledge base you wouldn’t otherwise have.

It also starts to get your name out there as being someone who is clued up and engaged.

Do you think being an entrepreneur is something you are or something you can become?

I believe that there’s no such thing as entrepreneurs, as such.

What you’ve got are people who are entrepreneurial thinkers and then you’ve got founders. To my mind this is a much more useful distinction. And I think that there’s a big difference between the two.

Having the mindset of thinking about everything you do and how it could be improved to find new value is being an entrepreneurial thinker. It’s that obsession with making things better and solving problems.

And then whether you become a founder or not is separate.

Whether you actually take the plunge, set up a corporate entity, go for investment or decide to be a CEO, is distinct from thinking entrepreneurially.

What is the hardest thing you’ve found about moving from practicing as a lawyer, into legaltech and being a founder. And what’s been the best thing about that?

The hardest thing has been to stop thinking like a lawyer.

As a founder and CEO, a lot of what you need to do is nothing like what a lawyer needs to do. As a CEO and founder, you need to set the vision, define the strategy and potentially push boundaries, whether that’s through cramming value into your product or driving sales.

And that’s when you can run into your inner lawyer.

That voice is more questioning, critical and asks questions like ‘is this too risky?’ or ‘is this the right thing to do at the right time?’ and so on.

That said, having been a lawyer, and working in and for software companies, I often replay some of the conversations I had in those roles. I try to get into the shoes of the lawyers and business users who have the problems Summize solves. This has been helpful throughout my time at Summize.

What’s the biggest difference between being a lawyer and a business person?

As a lawyer, you are mainly there to manage other people’s risks, and generally worry about their problems so they don’t have to.

You’re also a facilitator. You help the business do what they do best and ensure they do it safely and within the law or the parameters of the commercial contracts they sign up to.

As a business person, especially a CEO and founder, the emphasis is almost opposite.

It’s much more commercial. You have more latitude to take risks because the risks are ultimately your own to choose, not those of others to whom you are advising.

And you know what? It’s tough making that switch. You have to really change gears mentally and actively. But it’s incredibly fun. And very rewarding.

You go from being exclusively focused on downside risk as a lawyer, to being aware of that but ultimately looking for the upside opportunity. You start to see risk and reward as two sides of the same coin.

What are the most surprising and least surprising things you’ve experienced since starting a business?

The most surprising thing is that it feels like there’s a lot of lawyers who’ve gone into legaltech and founded a company or built a product.

However, despite this, so many products don’t capture the day-to-day life of a lawyer, and that of their colleagues in adjacent roles such as compliance, revenue assurance or sales, etc.

A lot of products are designed narrowly for a lawyer, but not for other and perhaps larger group of personas that also work with contracts. Again, I find that surprising. It seems a missed opportunity not to think more holistically.

There are also a lot of products throwing cool tech at problems without actually solving them.

In terms of what has been least surprising, and this is more of a personal one, but I thought the transition from GC to CEO would be a big one. I was ready for something ridiculously stressful. I was expecting to have those moments where you’re feeling up against it and thought it was going to be overwhelming.

So far it’s been anything but that. It’s been amazing. I love the engagement I have all the time with the product and the business, and the reward I get trying to inspire and build the team.

There’s a lot of transferable skills from GC to CEO.

I think if you take on a lot of responsibility as a GC in fast growing companies early in your career, you can build a really good set of skills and experiences that can make the shift to a leading business role a lot easier.

That said, you need to manage the mindset shift from being a problem solver — from a risk perspective as a lawyer — and instead become a better problem solver from an opportunity perspective as a business person.

If you have that set of experiences, the entrepreneurial mindset, the grit to be a founder and are able to change mindsets, you can switch from lawyering to being a CEO.

On the point of transferable skills, what do you think those are? We get asked this one a lot, including how to present skills learnt as a lawyer in a way that business people hiring you might best understand.

At Summize we have this series on creativity in law, and I think fundamentally what you are as a lawyer is a problem solver.

It’s a subjective area. It’s an area that requires opinion and interpretation of a set of facts from a contract or a situation. In many cases, you need to complete that process very quickly and accurately appraise a course of action, based on the information to hand.

You get good at making risk weighted decisions. You also develop a keen eye for issue spotting and identifying dependencies. This is definitely something non-legal professionals sometimes lack.

The best lawyers are also particularly good at discounting edge cases and focusing on the red flags and moving the business along without being the ‘department of no’. ‘Being commercial’ is the other way of describing this skillset.

That doesn’t mean you constantly throw caution to the wind and ignore risk as a ‘yes-person’ to the business. But you understand the business, it’s drivers and what is and isn’t important in the grand scheme of things.

Clients value lawyers who master the business and understand perspective. Good lawyers help navigate stormy or fair seas, and only steer ships back to shore if absolutely necessary and not every time a cloud appears on the horizon.

As a lawyer you get good at crunching a lot of variables, analysing them and providing coherent specific advice to solve problems. And I think when you are a CEO, or as a leader in a business, you need to apply similar skills, albeit for a different purpose.

I think if lawyers adopt these more entrepreneurial and commercial qualities, and pair them with an understanding of process improvement philosophies such as Kaizen, it could be game changing.

Right now legal remains tied to precedent, whether it’s what course of action to take, or how to draft a document, or how to send an email. Falling back on ‘this is the way we’ve always done it’ without pausing to zoom out and ask ‘is this the way we should be doing it?’ would unlock so much value for lawyers and their clients.

You’re obviously big on personal development and continuous improvement, both for business but also at the individual level. Do you have any advice about this subject?

Never sacrifice personal development. Never sacrifice learning or investing in yourself.

I say this because I did sacrifice personal development at different times. And I’ve always regretted it. Thankfully, I reprioritized how I think about things and make sure that personal development is something I no longer sacrifice.

After working in so many tech companies, I was taken aback at how much everyone put into their personal development; listening to podcasts, reading books, experimenting with new ideas. So I listened and learnt and figured out what interested me, and made a point of cramming personal development into my commute and spare time.

This massively changed my entire outlook and gave me the drive to start a business and pull together the various threads of my career into a new direction.

It made a big difference to how I went about my job and my interactions with colleagues.

Would you recommend any books or other media that have helped you or that you found interesting?

I’d recommend the following:

• The Spirit of Kaizen by Robert Maurer. Maurer is on the faculty of the UCLA and University of Washington Schools of Medicine, and a proponent of evidence-based psychology into practical strategies for success. The book contains a wealth of simple but powerful techniques that can be applied to almost any workplace situation; especially when you’re trying to navigate radical change, high-pressure deadlines, and competition. These are the same methods of small, continual improvement that have been tested by the largest companies, such as Boeing, Toyota, and the U.S. Navy.
• Atomic Habits by James Clear. This book is centered around debunking the prevailing wisdom that you need to think big to change. His book explains how big change comes from the compound effect of hundreds of small decisions: from doing two push-ups a day, waking up five minutes earlier each day, or holding a single short phone call. An excellent and practical book for creating change and great habits, whether individually or beyond.
• Sapiens by Yuval Noah Harari. This book is really insightful in terms of how society has developed. Perhaps I’m biased given my fondness for Kaizen, but the book has a definite thread of continuous improvement theory when assessing how societies rise and fall and evolve and manage change. Really eye-opening!

⚡ Interested in legaltech careers like Tom’s? ⚡

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.

In this guide we provide a comprehensive overview of legaltech jobs, salaries, how to network within the legaltech community, how to build skills and experiences, and where and how to find legaltech jobs.

This guide forms part 2 of our 6 part series on careers in legaltech, legal ops and innovation.

We hope you can leverage this guide to find your dream role! 🙏

Good luck! 🤞

Get to know the legaltech community

Networking

We used to hate networking. We love it now. What changed? Three things:

1. Caring less about what other people think.
2. Being genuinely interested in the subject matter and people involved.
3. Doing more of it.

Accept that not everyone will like you, nor be interested in you. It’s a fact of life. Once you get past that, networking becomes a lot easier. Also remember, that for most people, networking is awkward and a bit unnatural. You may be just as uncomfortable approaching someone as they might be having you approach them. Talking to strangers is inherently unnatural.

But if you are genuinely interested in the subject matter and people involved, you’ll find it a lot easier to strike up natural and authentic conversations.

You may also find that outside staid legal networking events the people you meet — whether at events or otherwise — will be easier to talk to because they enjoy what they do. A lot of legal networking events don’t seem to have many attendees who genuinely enjoy what they do.

In terms of doing more networking…

Events / conferences / meet-ups

To do more networking, find events and meet-ups that bring together people interested in legaltech, ops and innovation.

You may also get to see live products demos and perhaps be allowed to test drive legaltech products. This is a great way to get to know the thought leaders, products and vendor contacts in this space.

Here are some ideas to get you started:

• Meetup.com provides up to date listings for all sorts of meet-ups. See here for a global and local list of legaltech meet-ups. Don’t see a meet-up relevant or local to you? Create one!
• Legal Hackers is another fantastic community. It’s a global movement (with local chapters) of lawyers, policymakers, designers, technologists, and academics who explore and develop creative solutions to some of the most pressing issues at the intersection of law and technology. Through local meet-ups, hackathons, and workshops, Legal Hackers spot issues and opportunities where technology can improve and inform the practice of law and where law, legal practice, and policy can adapt to rapidly changing technology.
• LegalGeek. Don’t be put off by the slightly hip(ster) vibes. LegalGeek is a fantastic event and community. It’s incredibly popular and regularly puts together fantastic events, including their annual conference. Expect a very diverse mix of people, bitesize talks, sometimes contrarian views and lots of product demos and showcases.
• FutureLawyer is a slightly more formal affair, and in recent years has been split into sector specific tracks for private practice and in-house. The event covers a range of speakers, including vendors, thought leaders, and legal professionals.
• Legal Innovators is similar to, and run by the same folk as Future Lawyer.
• ILTA, the International Legal Technology Association is one of the longest standing industry groups and event organisations (run by members) focused on legaltech. Its events are huge, especially the US event, which has been held at Disney World and in Las Vegas.
• Inspire.Legal aspires to be an unconference. They aim to avoid simply rehashing the same tired conversations revolving around the brightest, shiniest new tech widgets in the market — widgets that frequently feel like solutions in search of problems.
• CLOC focuses on in-house legal operations, which inevitably emphasise people, process and technology. It’s a great event for anyone. If you work in private practice, it’s worth a look to understand your clients’ operational drivers (beyond the pure legals) in better detail.

How to build skills & experience

Legaltech training contracts

Wait… this is a thing? Yes. A few UK firms have launched training contracts that either:

1️⃣ combine (a) traditional legal training with (b) training in legaltech, product management, project management, process design and legal operations generally; or

2️⃣ focus exclusively on (b).

For option 1️⃣ , at the programme’s completion you do qualify as a solicitor of England & Wales and enter into a practising legal role.

For option 2️⃣ , at the programme’s completion you don’t qualify as a solicitor, but instead work on internal technology and ops projects at the law firm.

A&O’s Advanced Delivery Graduate Programme

Who is this for?

Per the website, “graduates with strong A-levels and ideally STEM or Economics degrees to be part of a team using the latest tools and software to bring legal expertise to the world in new and surprising ways”.

What you’ll do

The programme mirrors the structure of a training contract and is currently limited to 4 trainees.

Beginning each September, candidates undertake four, six-month rotations in:

• The Markets Innovation Group, one of the firm’s newest practice areas, which develops specific legal solutions for clients using technology, drawing on other aspects of the below teams where appropriate.
• The Project Management Office, A&O’s team focused on supporting delivery of legal work through application of project management frameworks and technologies.
• Legal Tech team, A&O’s team focused on selection through to implementation of emerging technologies into the firm’s legal practices and client facing tech driven services.
• eDiscovery, A&O’s team focused on use of eDiscovery and document review technology to expedite large scale legal reviews.

The trainees are based in Fuse, Allen & Overy’s London located tech innovation space, and are supported and funded in gaining a recognised qualification in project and/or process management and understanding its application through the provision of legal services.

Why consider?

If you’re not fussed, or at least unsure, about becoming a lawyer but interested in working for a large professional services firm and learning business operations, this role might be for you.

Where you’ll end up

Completion of the scheme may lead to a role within one of the above teams.

Do you qualify as a solicitor of England & Wales?

No.

Eligibility

To be eligible for the programme you will need A-levels — minimum AAB. Degree subject — various but ideally STEM or Economics.

How to apply?

The application window for 2021 has now closed — for context, key dates for the application window for the 2021 scheme was 14 December 2020–14 January 2021.

The application process comprises several stages:

1. Online application, including a Situational Judgement Test.

2. Assessment day (if online application successful), comprised of two one-on-one interviews. According to the website:

“The first interview will be a case study, focused on the type of work you will be exposed to in this role. You will have time to work through a short brief and prepare a short presentation to deliver to your interviewer. This will be followed by a discussion on the key points from the case study.

The second interview will assess your skills, knowledge and motivation for a career in our Advanced Delivery & Solutions Team. In addition, you will be asked a series of questions based on scenarios you would encounter during the graduate programme”

In terms of the general profile A&O is trying to hire into this programme, per the website this person fits the below description:

“We look for individuals with potential and passion. As well as a fascination with all things technology, we want to hear from open-minded, innovative candidates with a future-focus. These are the skills that will set your application apart and set you up for success. There isn’t one ‘type’ of person we’re looking for: we welcome applications from finalists and graduates who are passionate about commercial law and innovation with a degree background in Economics or a STEM subject.”

Where can I learn more?

See here for the A&O Advanced Delivery Graduate Programme website.

Clifford Chance’s IGNITE Programme

Who is this for?

Per the website, “[y]ou might have studied computer science. Or taught yourself to code in the evenings. Or be developing an app on the side of your law degree. The only thing you must have is an excitement for what the meeting of law and Tech can spark.”

It even has its own trailer:

Clearly a lot of work and investment has gone into the programme. Having worked with some of those involved in its running, we can say this is a solid and well-rounded programme, not a gimmick.

It’s a genuinely innovative attempt to modernise the training contract with substance, and generally address the increasing need for lawyers to be better equipped to understand and apply technology and innovation best practices to their work.

What you’ll do

According to CC, the IGNITE training contract mirrors the structure of a regular training contract: four seats, all six months in duration, around different CC departments.

However, unlike the traditional training contract, the programme has trainees assigned away from fee-earning to gain specific legaltech exposure.

More broadly, there will be a focus on how legaltech and digitisation are revolutionising the legal working environment. This includes working with the firm’s Best Delivery team, which focuses on identifying opportunities to redesign and implement better organisation of people, process and technology that enhance the firm’s client facing products and services.

IGNITE also includes the opportunity for secondments. These include secondments to some of the firm’s largest tech clients to advise on new tech solutions, and also to CC’s Applied Solutions team — the firm’s internal product development arm.

Why consider?

According to current IGNITE trainee, Adam Hunter:

“IGNITE has given me the opportunity to work on industry leading projects with lawyers across our global network and to meet with partners and clients to discuss their legal technology strategy. Alongside my Training Contract, my current IGNITE legal tech projects include designing and developing news solutions for a handful of the Firm’s global clients. Most recently, I seconded to one of the Firm’s largest tech clients, where I was able to advise on new tech solutions to some of the client’s most pressing challenges.

I also frequently work with our Best Delivery team to make our client matters more efficient, as well as provide training to colleagues, test new legal tech and contribute to client pitches. In March 2020, I was delighted to be recognised as one of the Top 10 Most Innovative Junior Lawyers in the UK by The Legal Technologist Magazine. In particular, IGNITE has helped me to develop the skills that are being demanded by our clients who are looking for their lawyers to not only have strong technical skills but to be commercial and entrepreneurial.”

Where you’ll end up

Upon qualification, INGITE trainees will have the opportunity to join one of Clifford Chance’s main practice areas:

• Finance
• Corporate
• Capital markets
• Litigation & dispute resolution
• Real estate
• Tax
• Pensions
• Employment

Having built up expertise and network within the firm’s legaltech and ops focused teams, there is likely opportunity to build on those experiences and connections within and outside the firm.

Do you qualify as a solicitor of England & Wales?

Yes.

Eligibility?

Applications are sought from candidates with a STEM background or other interest in tech, such as coding.

How to apply?

Applications for this year’s intake have now closed, but to give you an indication of the process as at the date of this article, it has historically looked like this:

• Applications open: 3 August 2020
• Applications close: 10 December 2020
• Assessment dates: w/c 8 February 2021

Selection process:

• Online application form;
• Watson Glaser test (see here for some tips by a current Baker & McKenzie trainee); and
• Two assessment days. The first is the same as the Training Contract assessment day, which includes one interview with a written case study element. The second stage is an IGNITE-specific case study interview.

Want some tips on how to apply? Future IGNITE trainee, Lorraine Chimbga has got it covered:

Where can I learn more?

See here for the Clifford Chance IGNITE recruitment website.

Volunteer to use legaltech in what you already do

Get to know your legaltech / innovation / tech team

If you already work in a legal organisation or team, speak to your IT / innovation / legaltech / emerging technology team. Find out what tools they have and what goes where in terms of your practice. Be bold and creative, actively seek their help on how to solve your day-to-day work processes! They will probably enjoy the challenge and the chance to shine.

Become a Microsoft Power User

Even easier, become a better user of techtech such as Microsoft Word. To do so, check out this amazing series by Crafty Counsel.

To whet your appetite, see this short video demonstrating how to move and swap rows in Word (without copy / paste) — this usually blows the minds of most lawyers when we show it to people!

Source: here

Skill up on Microsoft Excel. It’s really not that scary and super powerful for a lot of typical business tasks, and of course, for analysing data and presenting it. To get you started, Crafty Counsel have you covered with some intro videos on basic to intermediate Excel features for legal use cases — see here.

As obvious as this is, googling “how do I do X in Excel?” leads to many specific and excellent tutorials online.

Why are we flagging the obvious?

Because too often we encounter a total lack of curiosity when it comes to Excel among lawyers. Partly this is because most lawyers say they got into law because they weren’t good at maths. You don’t need to be a maths genius to use Excel.

ExcelJet and ExcelEasy are two great resources we frequently use to look up ‘how tos’ for specific use cases we are trying to achieve in Excel, e.g. how to count the number of occurrences of a specific value in a table, how to count the number of rows that have an entry matching X and Y but not Z, how to lookup data across multiple sheets and combine the two etc.

Be curious, get learning!

All super useful if you are summarising or analysing a table of due diligence data to produce actionable insights in order to advise your client! Or perhaps you are crunching matter data to produce better pricing models?

Yes, for any data nerds there are of course better options for large scale data exercises, including using SQL databases or other database constructs, and / or more powerful visualisation applications, e.g. PowerBi or Tableau. But for most lawyers, getting better at Excel is a start, and may in time lead to an understanding of databases and more advanced visualisation tools.

Don’t use Microsoft but use Google? No excuses, become Google Power User

Crafty Counsel also has this covered. See this excellent series on using Google Workspaces to enhance legal work productivity.

If you’re not a Google Workspace user but considering the switch, please feel free to use one of the below codes at this link to receive a 10% discount off for your first year of either:

• The Business Starter Plan with this code: FDGKJQX47DP69PX
• The Business Standard plan with this code: K4PHXELLGE79UQY

Note: if you use the above link / codes we receive a small commission which helps pay for our running costs.

Use more legaltech

How can you use more legaltech? Simple wins can be adopting tools like Litera ContractCompanion or Define, which respectively provide automated proofreading for legal specific typos (e.g. capitalised but undefined terms or missing cross-references) and easier comprehension of nested defined terms and clauses.

The best part? Both work inside Microsoft Word where you are most likely already working!

If you have eDiscovery like Nuix or Relativity, or contract analysis tools like Kira, try and get a demo at work. Yes, these tools are aimed at analysing big data, and no you may not do litigation or due diligence (their primary use cases), but can you think creatively about broader uses for your team? Perhaps you might mine your precedent data to draw new insights that might be actionable for internal or client facing value?

Get to know the IT or innovation folk who support these systems and similar. What’s their opinion? What do they think is the best tool in X or Y niche? This is also good to ask if you become interested in a niche and want to find a legaltech job there.

Better to know the best vendor to join before blindly leaping into a role at a vendor.

Volunteer for internal projects

Whether in-house or private practice, a great way for existing legal professionals to gain experience is to volunteer for internal innovation or similar projects.

A lot of legal organisations have technology or innovation committees, or similar permanent functions whose responsibilities may include any one or more of the following activities:

• problem identification
• process mapping
• continuous improvement
• product management
• selection of technology to buy or build
• technology implementation
• change management

Getting to know these teams and volunteering to help them in their activities can provide three benefits to you as a prospective legaltech career curious person:

1. Build expertise and skills relevant to legaltech, e.g. problem identification, process mapping, interviewing, designing, buying or building technology and getting it adopted. For one thing, you will better understand legaltech (and tech generally) in the sense that it isn’t simply about building or buying cool stuff — it’s about changing behaviours via a deep understanding of the user and their processes and drivers.
2. Widen your network, e.g. by meeting colleagues already involved in such projects, including specialists in legaltech and innovation or operations. By getting to know these individuals you can better understand who they are, what they do, how they do it and why… and whether they enjoy it. They may also have some invaluable views on which areas of legaltech — whether products and / or roles — are better or worse, or more or less suitable for you. Likewise they may have a view on similar teams at other organisations and whether those teams are better or worse than others. Their network might also provide handy connections for you to leverage.
3. Taste test your interest in, and suitability for, legaltech roles. If you decide you don’t like the domain or find it dull, you’ve lost nothing.

You might get involved in a variety of ways, e.g.

• providing feedback on problems or opportunities for innovation within your role / team / organisation;
• providing feedback, and possibly testing, different solutions to such problems; or
• helping map processes and contributing to discussions regarding their improvement.

How to get involved with these activities and teams?

Just ask!

It really is that simple. Most teams will encourage and enjoy your support as it’s often tricky to find people to help out with internal innovation activities, especially within law firms where billable hours tend not to reward innovation activity (with a few notable exceptions, e.g. CMS, Reed Smith and Mishcon de Reya) and therefore innovation activities are second class citizens in terms of priority.

Volunteer for (or build your own) innovation secondments

Some law firms have official or sometimes unofficial secondments to innovation teams.

Freshfields has an official programme that allows individuals to apply for a 6 month stint in their innovation team, working full-time on innovation projects including legaltech selection through to implementation, as well as build outs for new technology solutions.

We also know of at least one individual, a senior associate at a large firm, that pitched their leadership team on the idea of creating an innovation role and being the first person to trial it. It was a winning proposition, they completed the secondment and pulled together many different innovation threads among and between different parts of the business and this is now a permanent function of the firm for others to rotate in and out of as part of plans to widen this team over time.

Similarly, in response to trainee interest and a similar pitch, two London trainees at Reed Smith were selected to undertake an innovation seat. The innovation seat allows trainees to split their time between a “traditional legal practice seat” and one of the firm’s innovation projects. Previous projects have included developing automated services for clients, working on a new knowledge analytics platform and helping to develop the firm’s service design methodology. To prepare for the innovation seats, Reed Smith ran a summer programme in collaboration with independent consultancy Janders Dean (now a part of Morae Global). That programme taught trainees skills such as problem identification and solving, design thinking and understanding the impact of legal technology.

Seeing a theme?

Volunteering is an easy way to build experience and network…

Volunteer to help start-ups, scale-ups and others

You’d be surprised how many start-ups and scale-ups encourage or will accept help from interested individuals. And yes, that includes unsolicited help!

Many businesses are always looking for people to test their products and provide feedback to inform product management (i.e. to ensure the product is usable and solves a user’s need) and user testing (i.e. to make sure the product is bug free and easy to use).

Reach out to companies.

Ask them if they would like your help with product testing and feedback. If you are a legal professional, your legal experience and familiarity with the types of problems legaltech products aim to solve can be invaluable.

But don’t forget other avenues. Be creative. Literally.

Offer to create content for a legaltech vendor’s blog. This can be a great way to help them. Blogs (including this one) are always looking for great content (get in touch to contribute to lawtomated).

Contributing to vendor or legaltech specific blogs like this one is also a great way to build a brand for yourself in this domain. This can make you more attractive to employers, demonstrating your expertise and involvement. It provides some social proof you are interested and active in this space vs. casually interested.

And of course, helping out builds reciprocity.

Per Robert Cialdini’s famous book, Influence, humans are hardwired to give back to others the form of a behaviour, gift, or service that they have received first. This is why people try and buy drinks for others, and equally why people actively refuse them, i.e. acceptance makes it very hard to not return the favour in some form or another… If you’ve ever had someone buy a drink for you without you asking, you will know the discomfort of rejecting that advance, and the almost physical struggle to reject that gift. This is also why salespeople, shops and charities give you something free — you feel obliged to return the favour and buy something or make a donation.

But equally, if someone does something genuinely nice and for your benefit, you will feel very positively toward them and actively seek an opportunity to return the favour.

Volunteering to help a start-up, scale-up or blog — and genuinely seek to add value — is not only a great way to gain experience, but may build reciprocity that returns dividends later on, e.g. a referral for a job, a valuable introduction or even a job offer!

Volunteering in this way is also another easy and low risk way to test whether or not you are really interested in the space or casually tempted.

Volunteer to help out on an open source project

If you aren’t familiar with open source, it is a type of computer software in which source code is released — usually but not always for free — under a license in which the copyright holder grants users the rights to use, study, change, and distribute the software to anyone and for any purpose. It is often developed collaboratively. People work on code improvements or suggest amendments ad hoc as they encounter them. We’ve also written on the idea of open source contracts — see here.

If you have technical skills and can code, contribute to an open source legaltech project, for instance:

• Docassemble, an open source document assembly project (software that automates the creation of documents).
• The Accord Project, an open source project focused on creating mechanisms for smart legal contracts. A smart contract is an enforceable agreement, automatable by computer, although some parts may require human input and control.
• This DocuSign/Docassemble integration open sourced by Radiant Law, an excellent ALSP and consultancy focused on legal ops and innovation.

Most of the internet runs on open source technology, and one of the most popular computer operating systems for back-end internet services is the open source Linux system.

Things to learn

Design thinking, process mapping, product mgmt

Tied to the above, you will very likely start to learn about design thinking, process mapping and product management. These are three super helpful and somewhat overlapping skills relevant to most legaltech roles.

What is design thinking?

Design thinking is a methodology that provides a solution-based approach to solving problems.

Ok… so what?

It’s extremely useful for tackling complex problems that are ill-defined or unknown. And this is often the case when trying to dig into a particular problem or opportunity for innovation.

It’s often easy to feel something could be improved (or is broken) but much harder to pin down first and foremost the root causes for that feeling, and by extension how to solve for it.

Design thinking provides a framework of exercises and principles that work by understanding the human needs involved, by re-framing the problem in human-centric ways, by creating many ideas in brainstorming sessions, and by adopting a hands-on approach in prototyping and testing.

The typical design thinking process, as popularised by Stanford University’s famous dschool looks like this:

Understanding these five stages of design thinking will empower anyone to apply the underlying methods in order to solve complex problems that occur around us — in your organisation or elsewhere.

Being able to understand and apply these skills can demonstrate many of the skills that typically feature in legaltech job descriptions for many legaltech related roles, from sales to marketing to product to engagement and so on.

These skills and techniques are increasingly in demand for many innovation related roles, which are principally about finding the right people, processes and problems to solve with the appropriate priorities.

Design thinking provides a way to go from vaguely defined problems, needs and wants to solutions that add value for a set of defined users.

Where can I learn more?

• Stanford dschool’s Design Thinking Bootleg. The Design Thinking Bootleg is a 90 page free pdf summarising the set of tools and methods that the Stanford dschool teach on their famous design thinking courses. Well worth a look. It’s an easy and concise guide to the fundamental methods and exercises used to apply design thinking in solution to problems.
• This is Service Design Doing. Related to design thinking is service design. Service design is focused on planning and organising people, infrastructure, communication and material components of a service in order to improve its quality and the interaction between the service provider and its users. Service design may function as a way to inform changes to an existing service or create a new service entirely. Increasingly applied in legal as a means for critically and collaboratively interrogating the current and desired state service between providers and consumers of legal services.
• Other great books that provide some excellent and very visual explanations about how to apply various business oriented design thinking skills include Strategizer’s series of books, including: Business Model Generation, Value Proposition Design and Testing Business Models. Each provides a wealth of popular templates such as the Business Model Canvas and the Customer Value Proposition Canvas, which can help design, test and refine business and customer value propositions to ensure problem and persona fit for new or improved products or services.

What is process mapping?

A process map is a planning and management tool. It visually describes the flow of work in a system.

Process maps show a series of inputs, teams and / or individuals, and events that produce an end result.

A process map is also called a flowchart, process flowchart, process chart, functional process chart, functional flowchart, process model, workflow diagram, business flow diagram or process flow diagram.

Here’s one we made earlier:

In a nutshell it shows who does what, how, where, with whom, when and why in a process and can be used in any business or organization. They are ideally mapped collaboratively among the relevant stakeholders to a process, which helps align everyone’s understanding of the process, which may otherwise differ if developed in silos.

It provides a way to identify areas for improvement, e.g. bottlenecks. These opportunities to improve the process often present as the 7Rs, i.e. opportunities to: rethink, reconfigure, re-sequence, relocate, reduce, reassign, retool the process.

This usually leads to a redesigned process, or desired state process — the target new process. Going through this exercise of first mapping the current state and using that to develop a desired state process makes it easier to plan and prioritise what and how to improve the process.

There are many related methodologies that prescribe different process mapping exercises, purposes and visual elements to represent systems.

Rather than being too focused on these at first, it’s best to get a general understanding of the business purpose of process mapping. A great way to do this is to map a simple process you work with every day and analyse it for improvements. Don’t get too fixated on the exact flowchart elements to use.

Where can I learn more?

• Start with this excellent guide by creatley. It does a nice job of explaining entry level background to process mapping and illustrates how to apply it in real life, including the basis and most common flowchart elements used to map a process.
• For a slightly more in-depth and legal specific guide, see here.
• If you are interested in dipping your toe into lean thinking, another improvement methodology that relies heavily on process mapping then check out This is Lean. It is a breezy but complete primer on lean principles. Lean thinking is an approach to process improvement developed at Toyota in the 1950s to create the Toyota Production System, i.e. the system and principles that guide Toyota’s famously reliable and value driven manufacturing. Lean principles provide a framework for creating an efficient and effective organization. Lean allows managers to discover inefficiencies in their organization and deliver better value to customers. The principles encourage creating better flow in work processes and developing a continuous improvement culture.
• If you enjoy This is Lean, we suggest you dive into the original (and some say best) guide — The Toyota Way. The Toyota Way explains in great detail the Toyota Production System that inspired lean and its offspring (e.g. including the The Lean Start-up).

What is product management?

Product management is the role and function within an organization that is responsible for a product’s overall success.

Product Managers work with groups inside and outside of the company to build and execute a plan to make sure the product best meets its user’s goals, and in turn the financial and strategic goals of the business producing that product.

Defining a product manager is tricky.

Specific responsibilities vary depending on the size of the organization, and sometimes the types of products being produced.

In larger organisations, product managers embed within teams of specialists. Researchers, analysts, and marketers help gather input, while developers and designers manage the day-to-day execution, draw-up designs, test prototypes, and find bugs. These product managers have more help but… they also spend more time aligning theses stakeholders behind a specific vision.

Product managers at smaller organisations usually spend less time getting everyone to agree, and more time doing the hands on work that comes with defining a vision and seeing it through into a customer facing product.

At a high level, there are quite a number of overlaps with project management.

Product management is about:

• Understanding and representing user needs, by first getting to know and empathising with users and collecting diverse data to validate hypothesis and prove or disprove assumptions about wants and needs and existing vs. desired behaviours and values (this is where Design Thinking overlaps, and is a tool in the product manager’s arsenal).
• Monitoring the market and developing competitive analyses.
• Defining a vision for a product.
• Aligning stakeholders around the vision for the product.
• Prioritizing product features and capabilities, and creating and maintaining two-way communication between users and the business regarding the product’s development.
• Creating a shared brain across larger teams to empower independent decision making.

Where can I learn more?

01. To begin with, we recommend you check out Atlassian’s guide here. Atlassian make many fantastic user driven developer focused products, including Trello (which we use to plan lawtomated’s content and activities!), Jira and Confluence. Note this guide also digs into related methodologies common to product management, including Agile, Scrum and Kanban as well as core product management tools such as product roadmaps.

02. Diving deeper, check out Ken Norton’s blog. Ken is a long-time product manager at Google and product management coach. His blog shares many of his insights from doing and teaching product management

03. For an excellent and well-rounded resource collection this collection of the Top 100 Resources for Product Managers is invaluable to anyone interested in, or working in, this role.

That guide, put together by Sachin Rekhi, an experienced product manager, is divided into 6 sections:

• overview, covering product management and the role of product manager in general;
• vision, how to define and communicate vision), strategy (how to ensure successful products happen;
• design, techniques for designing and building great products), execution (how to make it happen);
• growth, how to grow product… it’s no good making cool stuff and hoping people come;
• leadership, how to influence and build buy-in; and
• careers in product management.

Why are these skills useful to legaltech roles?

Legaltech and the roles behind it are not all about coding and software skills.

Far from it.

Legaltech and the roles behind it are about being able to identify the people, process, problems and priorities worth solving and where appropriate knowing enough about technology to be targeted in what you buy, build or re-use.

This is especially so within larger organisations, e.g. for innovation roles.

But it is equally important for vendor side roles where cracking product-market fit can make or break the business. And cracking that goes well beyond clever code. Smart vendors often leverage existing technologies rather than reinvent the wheel from the code up, instead focussing intently on users, their jobs to be done and product fit.

So it is no surprise most legaltech job descriptions increasingly select for experience or skills in these areas, and sometimes specific qualifications.

Should I learn to code?

Generally speaking, probably not

Unless you are really excited by coding, we’d focus on the other skills and activities described here. If you want a more detailed explanation as to why we recommend this course of action, see here.

We say all of this as the lawtomated team includes experienced lawyer / coder hybrids, working with a mix of professional developers and other non-legal professionals, including product, process analysts, project managers and so on.

Those of us that code, rarely code on the job (instead relying on professional developers), albeit that background makes for productive conversations with technologists and vendors, but it isn’t an overwhelming advantage.

But if you are tempted…

We suggest the below resources. For more resources, please get in touch.

⚡ Automate the Boring Stuff With Python

Focuses on learning to code in the context of solving the many boring tasks that are core to legal and legal adjacent processes, i.e. many of which legaltech products target. Its focus on learning by doing is always recommended, especially with coding.

You’ll learn more by building something than learning a few basic coding components in the abstract.

See also here for the free online only version.

⚡ Freecodecamp

A free online and self-paced coding bootcamp that takes you from beginner to a reasonably advanced level of software development knowledge.

The course is now pretty huge. It covers the following skills and technologies:

• Responsive Web Design Certification (300 hours)
• JavaScript Algorithms and Data Structures Certification (300 hours)
• Front End Libraries Certification (300 hours)
• Data Visualization Certification (300 hours)
• APIs and Microservices Certification (300 hours)
• Quality Assurance Certification (300 hours)
• Scientific Computing with Python Certification (300 hours)
• Data Analysis with Python Certification (300 hours)
• Information Security Certification (300 hours)
• Machine Learning with Python Certification (300 hours)
• Coding Interview Prep (Thousands of hours of challenges)

Graduates of this free course have landed jobs at big tech companies such as Google, Amazon, Spotify and Microsoft.

⚡ Harvard’s CS50 via edX

For an undergraduate overview of several fundamental computer science principles and how these translate into actual code and, by the end of the course, have you building simple web apps, we recommend CS50.

Best of all, it’s free to take (albeit a certificate of completion is available for a small charge).

CS50 is one of, if not the, best rated online course.

We took this course (in addition to having previously studied software development full-time) and it’s brilliant.

David Malan, the tutor, is phenomenal in his enthusiasm and ability to deconstruct the complex via memorable analogies and worked examples and lively demonstrations.

He’s the CS teacher we wish we had at school! Likewise, his supporting tutors are brilliant.

The course starts with Scratch, an excellent visual programming language aimed at children (albeit can be used to build some pretty involved apps), and quickly ramps up the learning curve, jumping into C for several weeks before moving on to easier programming languages such as Python and JavaScript.

At the end of CS50 you will:

• Have a broad and robust understanding of computer science and programming.
• Know know to think algorithmically and solve programming problems efficiently.
• Understand concepts like abstraction, algorithms, data structures, encapsulation, resource management, security, software engineering, and web development.
• Have familiarity in a number of languages, including C, Python, SQL, and JavaScript plus CSS and HTML.
• Understand how to develop and present a final programming project to your friends, family or peers.

One of the best things is that the first part of the course teaches the C programming language.

This is a lower level language, i.e. closer to what machines natively understand and less easy to read as a human. It also requires you to better understand how a computer allocates memory to different jobs.

Why is this good?

It forces you to think much more like a computer, and in turn helps aid intuition about lower level functions within a computer such as memory and memory management.

In doing so, you’ll better understand computer hardware and software whilst really appreciating how much is beneficially abstracted for you in higher level languages such as Python or JavaScript… and how easy those languages make software development!

Build things

What things?

Whether or not you can code, consider building something. Are there any problems you face in your daily life that have a legal or similar emphasis that could be better engineered?

Believe it or not, this is also one of the most recommended (and best) ways to find ideas for start-ups (if you are so minded). For instance, Paul Graham, Ycombinator founder and Silicon Valley investor and sponsor for huge start-ups like AirBnB, recommends you are better off starting with problems not business ideas.

Why not have a go at designing a solution and then… building it?

Why not combine this with the above process mapping, product management and design thinking skills and exercises?

If you can, take it a step further and actually build it!

How?

See below… 👇

How to build things

You can either build something with a more technical co-founder, or do it yourself with the increasing number of no or low code app building solutions.

The growth, power, usability and flexibility of no code tools is another reason we are bearish on the need for lawyers to code.

Wireframe

It doesn’t have to be perfect, or even working. It could just be mock-ups (also known as a wireframe) of the app and how it is intended to function, which can be done on a whiteboard, pieces of paper or a prototyping tool such as draw.io or balsamiq.

E.g. something like this:

Going through the process of problem identification, process mapping and thinking about the personas of those facing this problem will hep you understand how to apply skills necessary to many legaltech roles. You can also test your prototypes with real users, perhaps even a friendly colleague or two, and iterate your product.

No code app building

For instance check out the below no code app building platforms, many of which offer free trials:

• Bubble, a general purpose no code platform allowing anyone to build production ready web apps. Curious? Get started with their free trial here.
• Bryter, a popular no code workflow automation and app builder aimed at legal. Check out their free trial!
• Autto, another fantastic legal specific no code automation platform that allows you to build automated workflows and small apps. Check out their 1 month free trial!
• Avvoka, a no code document automation platform including other cool features for online negotiation and contract analytics. Check out their 14 day free trial here!

Macros

What’s a macro? A macro is a series of commands and instructions that you group together as a single command to accomplish a task automatically in the Microsoft Office application suite.

These are a little clunky to learn at first, but they can be surprisingly powerful.

Most law firms (and many organisations generally) have a litany of macros automating the most boring, repetitive actions within Microsoft Word and Excel.

Chances are that if you work in a legal organisation, you use macros all the time but may not realise which buttons in your Microsoft Word installation are custom to your organisation. If you spot any (i.e. functionality you don’t have on your home edition of Microsoft Word), they are likely macros built by you IT team.

Here’s a simple beginner’s guide to get you started on how they work and how to build and publish them.

Office 365

Microsoft 365 (formerly Office 365) offers a free developer account, complete with dummy datasets — see here.

With a developer account you can access the full Microsoft 365 set of applications and tutorials. A good place to start are the Microsoft Power Automate tutorials which allow you to design and build automated workflows for common office based tasks such as document automation, contract approval and dashboarding of basic data about these actions.

For some inspiration, see this excellent webinar by LawHawk for the centre for The Centre for Legal Innovation.

In this webinar they demonstrate a legal platform built using Microsoft 365. That workbench includes knowledge management functionality, NDA automation from drafting through to approvals and finally through to signing and filing… Impressive stuff. And absolutely something you could learn to build without knowing a ton of code.

And for a super quick how to, check out this 13 minute tutotiral on how to automate Word documents in 3 simple steps by LOD’s Amanda Fajerman:

Google Workspace

Crafty Counsel have collaborated with legaltech aficionados and legal ops gurus to provide a fantastic series of short tutorials demonstrating how to build automated workflows and other productivity hacks using Google Workspace (formerly Gsuite) products such as Google Sheets, Docs and Forms.

Check out the below for some further inspiration on how to build legaltech with stuff you already (likely) use:

🦊 Generating a bible index of legal documents in Google Drive

🦊 Using Google Sheets to automatically update numbers in Google Docs contracts

🦊 How to use Google Forms to automate a Google Doc contract

For the full series of tutorials, see here.

If you really want to code… automate the boring stuff

For something more adventurous, and for someone who wants to code (or can code a bit) check out Automate the Boring Stuff With Python (see also here for the free online only version). This is a fantastic resource for budding coders.

It’s aimed at anyone who has spent hours renaming files or updating hundreds of spreadsheets or Word documents.

This guide teaches you basic python coding skills, and importantly does so via real world examples of how to automate the most boring bits of most office jobs, including many automations that form the primary selling points of well known legaltech!

Learn how to automate tasks such as:

• search for text in a file or across multiple files;
• create, update, move, and rename files and folders;
• search the Web and download online content;
• update and format data in Excel spreadsheets of any size;
• split, merge, watermark, and encrypt PDFs;
• send reminder emails and text notifications; and
• fill out online forms.

Legaltech masters / university / other courses

In the past 2–3 years there has been a growing number of legaltech and legal innovation courses offered by universities and the providers of the GDL and LPC.

Examples include:

• MSc Legaltechnology, The University of Law. £8,5750 (domestic) — £12,360 (international).
• Law and Legaltech LLM, The University of Portsmouth. £9,200 (domestic) — £16,400 (international)
• Legaltech LLM, The University of Swansea. £8,250 (domestic) — £15,850 (international).

There are literally 10s of such courses, including across the USA, EU and beyond.

Rather than list these courses and their basic details, we will try and explain how best to think about and analyse these courses, plus provide our view on their worth. At the end of this section we include references to two directories of such courses.

Do we recommend them?

First, a disclaimer: we’ve not studied these courses. So please read the below in that context and with that understanding.

We’d also say that these courses remain relatively new so it’s a little tricky to determine their success / fail at providing what students need and how this aligns with their wider aims, including career ones.

But to begin with, the question of whether or not we’d recommend them depends on why you are studying the course.

What are you looking to learn? (and why?)

Broadly speaking — and this is a generalisation — the courses tend to divide into courses focused more on:

1. the intersection of law and emerging technologies such as AI and blockchain, and the novel legal issues that this creates; or
2. legaltech, legal ops and innovation, i.e. how to identify people, process and technology within legal businesses that can be improved and the means with which to improve and deliver high ROI solutions.

If you are, or want to be, a lawyer advising clients at the intersection of law and technology, i.e. providing legal advice and other legal services, courses that fall under the first definition might be for you.

However, if you want to work on legaltech projects or products, whether in-house, in a law firm or vendor side, you might wish to focus on courses that fall under the second definition.

In practice, there are a lot of courses that seem to straddle both definitions. Be mindful of this distinction and think about what you really want to focus on, and where you hope the course leads.

Hands-on better than hands-off

As a general rule, our opinion (and it is only our opinion) is that it is better to get hands-on experience with legaltech and innovation projects vs. studying them and the underlying theory.

Why is that?

Legaltech and adjacent subjects are changing all the time. New vendors spring up and sometimes die within the course of a single year. What was cutting edge 6 months ago may be old news tomorrow. See here for an increasingly busy graveyard of legaltech companies that have been wound up in recent years.

A lot of legaltech roles are very hands-on. They mostly involve a lot of hard graft meeting people, interviewing them, listening, trying to distill exactly what they need from what they want and reading between the lines to draw useful insights that inform decisions about what problems, processes and priorities there are to solve and how best to do so, whether using tech or not.

Most of these skills do not seem to feature in many of the courses we’ve researched.

Some courses do seem to offer this aspect, i.e. graded projects to identify problems worth solving and using industry best practices and similar drawn from other domains (e.g. product management, design thinking or process analysis) to build apps or tech enabled services in solution of such problems. In some cases these exercises are run in conjunction with law firms and vendors to make the challenges and feedback realistic and valuable. These courses look more promising if you favour a hand-on approach and wish to focus on legaltech and legal operations vs. the intersection of law and tech from an academic legal perspective.

Likewise, many courses are taught, at least in part, by practitioners working in legaltech. But again, be careful to enquire and understand who these people are — are they lawyers advising clients about AI or lawyers building AI related legal products and services? Depending on whether you are interested in the legal side or the legaltech side, this could make a massive difference to how useful or interesting these inputs might be.

Finally, if a course offers lectures and projects run by or with legaltech practitioners, it can also be a good networking opportunity to learn more about roles in the space and perhaps find a route into legaltech jobs and similar post-qualification.

Legaltech employment opportunities and references

Like any course taken with a career ambition in mind, be sure to carefully evaluate the course’s stated employment opportunities.

Ask for references to graduates that have completed the course and what they do now.

This is the best way to assess whether the course leads to roles you are interested in, and also to sense check whether or not the course was determinative in that outcome, e.g. was it the course that led to the employment opportunity or was it the candidate’s other background, skills, experiences and connections? If the latter, what were those other determining factors and how could you acquire them?

If you can, try and speak to graduates 1 to 1 and without the course provider listening in.

You will get a much more candid view if you do. We’ve done this in the past regarding courses we’ve taken or researched and it has in many, if not all, cases helped us avoid bad decisions and make better ones.

A general comment on legal education

We’d also say that the very real gaps in legal education that such courses seek to address would be better solved by embedding into traditional legal degrees greater emphasis — perhaps via optional 2nd or final year modules — on the modern aspects of legal practice, including legal innovation, legaltech and legal ops along with useful skills such as project and product management basics and process and design thinking skills.

Making these optional would allow students interested in the academic side (99% of most modern law degrees) to follow that path, yet at the same time allow practically inclined students to diverge and study the more modern aspects of actual legal work.

The jury is out on need

The other reason we’d caution against rushing into legaltech or legal innovation courses is that they aren’t yet, nor seem likely to be, a requirement for most entry level legaltech jobs in the space.

Most job descriptions in the space make no specific reference to such courses, albeit some of the knowledge and skills learnt on such courses may help demonstrate the relevant skills, experience and interest in the sector.

One reason for this is a slow but increasing trend in legaltech to select and hire individuals expert in non-legal domains, e.g. actual product managers, actual data scientists, actual business analysts and so on from areas such as tech, consulting etc.

This is a slight reversal in the more common trend, which involves re-training lawyers in these skills, or simply parachuting lawyers into such roles without any real training or experience despite also setting them unrealistic (and often ill-defined) goals tied to a total lack of incentives…

In other words, larger legal organisations and certainly most vendors these days, increasingly value non-legal expertise as much, if not more, than legal expertise. Adding more legal specific expertise to a legal background might not provide much value vs. such candidates.

You might instead be better off developing non-legal specific skills and experiences if you are approaching legaltech from a legal background.

But as we say, the jury is out on this one. So for now, this is us reading current trends and predicting out where the market will be in 3–5 years. We could be wrong, but we might be right.

For this reason, if you are already a lawyer or other legal professional, we’d suggest the other ideas described above, such as working on internal legal innovation projects, creating your own or volunteering to help out with start-ups and scale-ups in the space and so on.

And now for something different

As we were writing this piece, a great looking — and hands-on — course launched called exponential.legal.

This course, which — full disclosure — we haven’t taken, focuses on hands-on exercises and frameworks to identify, qualify, quantify and scale legal expertise using exponential technologies to deliver process transformation and creation of new or enhanced products and services.

According to the website, the course does the following:

“Getting Exponential: The Essentials certificate course is an introductory, maker-style course for legal professionals building a modern practice. Apply leverage to your existing legal expertise by creating legal value once, and delivering it widely.”

‍The bulk of this course will be consumed on demand, over 8 weeks (4–5 hrs per week), through a combination of recorded video content, written lessons, reference materials and (most importantly) guided activities, where students will:

• ‍learn what it means to scale your expertise;
• work through a framework for de-risking exponential ideas;
• develop a series of assets to be used beyond the course; and
• plot your next steps towards becoming exponential.

The outcome of the course is having successfully taken an idea through the launch lifecycle and have a series of assets to be used beyond the walls of the course.

The course is put together by a diverse set of experts in the legaltech and innovation space:

• Christie Guimond, Innovation & Engagement, White & Case;
• Dennis Kennedy, Director, Center for Law, Technology & Innovation, Michigan State University;
• Marc Lauritsen, President, Capstone Practice Systems; and
• Mike Capucci, Partner, FoundationLab.

Worth a look, particularly for experienced professionals trying to change their organisation.

It isn’t cheap, but cheaper than a typical masters: $499 for non-profits and government professionals, and $1,499 for industry professionals. There is also on spec pricing for organisations.

Where can I find a complete list of legaltech courses?

For a more detailed list of similar courses, including outside the UK (EU, USA and beyond) see:

• here for a simple list by jurisdiction; and
• here for a similar list, albeit with basic course details summarised.

Where to learn more about legaltech?

Websites like…

• Artificiallawyer and LegalITInsider, Lawsites for news; and
• This blog, The Time Blawg and Legal Evolution for thought pieces and industry deep dives and analysis;
• The Legal Technologist for magazine style monthly content, mixing guidance, interviews and product specific content; and
• The Legaltech Hub for a comprehensive listing of legaltech vendors, events and other legaltech related resources.

Podcasts like…

• Podcasts like the excellent Legaltech Arcade by Robert MacAdam, a former HighQ product manager and current VP of product management at BusyLamp.
• Legal Evolution covers the latest topics, trends and tech in the legal industry, including many legaltech, ops and innovation topics and speakers.
• The Legal Ops podcast is about all things legal operations, legal business and legal technology. It’s hosted by legal ops professionals Alex Rosenrauch and Elliot Leibu.
• The Wired Wig, a legal tech podcast for lawyers, law students and business leaders who are interested in how Law interacts with technology.
• How I built this, OK not a legaltech or even legal related, but it is excellent and contains 100s of interviews with successful business founders, telling the warts and all stories of how a lot of grit, good ideas (and bad), some luck and good timing made them and their business successful, often through innovation or an intent focus on a customer need. Stories include Spanx, AirBnB, Dell, Patagonia and many more. For a written guide to the podcasts in the series, we also recommend the accompanying book.

Free legaltech online courses like..

CS50 for Lawyers by Harvard University, via edX (free to learn) is a variation of Harvard University’s introduction to computer science, CS50.

Unlike the main CS50 course, CS50 for Lawyers is designed especially for lawyers (and law students).

Whereas CS50 itself takes a bottom-up approach, emphasising mastery of low-level concepts and implementation details thereof, this course takes a top-down approach, emphasising mastery of high-level concepts and design decisions related thereto.

The course teaches:

• computational thinking
• an introduction to programming languages
• algorithms, data structures
• cryptography
• cybersecurity
• internet technologies
• cloud computing
• web programming
• database design
• cybersecurity, continued
• challenges at the intersection of Law and Technology

Ultimately, it equips students with a deeper understanding of technology and how it relates to their day-to-day work and that of their clients, and more generally how software is changing the way business is conducted.

Highly recommended for anyone wanting to upskill their technology knowledge but not wanting to go down to the level of coding.

Legaltech twitter

Legaltech twitter is worth checking out. Find accounts to follow — search for #legaltech #lawtech to find conversations and accounts. To get you started, here’s a few accounts (in no particular order) to follow:

• @lawtomated, our account (we are also @lawtomated on LinkedIn, Instagram and Facebook)
• @artificiallawyer, legaltech news and views (also via www.artificiallawyer.com)
• @bobambrogi, Lawyer and journalist covering legal tech and innovation at http://LawSitesBlog.com and http://AboveTheLaw.com and through the podcast http://LawNext.com
• @nikiblack, legaltech evangelist a MyCase, lawyer, legal technology author and journalist
• @jborstein, advisor to Penn Law Future of Profession initiative, advisor to LegalMation and Legaltech investor
• @prestonjclark, founder of lawinsider
• @heyitsalexsu, lawyer turned salesman and director of business development @evisort
• @bamlegal, founder of bamlegal, legal engineer, lawyer and investor and FT Top 10 legal technologist and European Women of Legaltech Winner 2020
• @legalitinsider, Legal IT, a leading legaltech news source, edited by ex City Solicitor — Caroline Hill @chillmedia
• @legaltechnologist, legaltech magazine providing thought provoking articles on how technology is changing legal practice, edited by @doublemarc
• @TheTimeBlawg, the past, present and future practice of law (reality not hype). Brought to you by @BrianInkster of @inksters
• @nwaisb, CEO of @KiraSystems, Author of “AI for Lawyers”, former @WeilGotshal corporate lawyer, Canadian.
• @akhudek, CTO and co-founder of @KiraSystems
• @denniskennedy, Consulting innovator; Interim Director, Mich St U Cntr for Law, Tech and Innovation; author; speaker; co-host, Kennedy-Mighell Report podcast
• @JoannaMG22, London based journalist and author and frequent contribute to the Law Society Gazette on legaltech topics
• @alexgsmith, Product Lead for RAVN. Ex-Innovation at Reed Smith. Ex-Lexis product
• @clevy_law, legaltech evangelist and in-house lawyer
• @alexhamiltonrad, CEO and co-founder of Radiant Law, curious what happens if lawyers stop being so… lawyerly
• @AndrewArruda, founder of @RossIntel
• @ronfriedmann, Lawyer, analyst, marketer, blogger, ex-Bain, ex-econometrician
• @jackwshepherd, Ex-insolvency lawyer and legal tech @Freshfields, now @iManageRAVN
• @lawheroez, ex-GC & legal ops in tech. Now designs and builds solutions for law firms & law departments @ElevateServices
• @jplink, CEO of Clifford Chance Applied Solutions
• @cguimond11, Co-Founder of #SheBreakstheLaw
• @nicola_shaver, Legaltech & Data Geek, Innovation & Knowledge MD at Paul Hastings and founder of @legalechhub1
• @lauravanwyn, Co-founder of @diligensoftware
• @jaesunum, founder of @sixparsecs and leading thinking on legal and legaltech strategy and data backed insights
• @legal_ev, facts and commentary about a changing legal industry. Great long reads!

As with all such lists, we apologise to anyone we left out!

Please get in touch if you wish to be listed above or we missed out anyone super obvious but absent from the above list!

Fantastic jobs and where to find them

Your network

If you heeded the advice above regarding networking, events, meet-ups, getting to know colleagues who may already work in legaltech related teams, and volunteering to help start-ups and so on, you may find your best route into legalech is via your newly developed network.

Don’t be shy.

Sound out if anyone is looking to hire. Even if there isn’t a specific role, ask the question. Arm yourself with an elevator pitch as to why you’d like a role, what value you’d add and so on.

You’d be surprised how many legaltech jobs in this sector (and in general) are never advertised. Don’t miss out.

Recruiters

• LinkedIn increasingly features legaltech related roles. Setting up saved searches within LinkedIn’s jobs section for keywords such as “legaltech”, “legal ops”, “legal operations” and “legal innovation” can be a good way to surface related legaltech jobs as and when they get posted.
• Another great resource, begun as a side project, is Legaltechjobs.com. It’s probably the most comprehensive, easy to use, and up to date set of listings site for legaltech jobs.
• For specialist recruiters we recommend Harrier Search. Founded by Luminance’s first non-technical hire, Henry Venmore-Rowland, Harrier unsurprisingly have an in-depth and first-hand knowledge of the market and are well connected to many legaltech teams across private practice, in-house and vendor side. Henry genuinely cares about the space, the people in it and the roles he fulfils on behalf of his clients and candidates.

Speculatively apply to legaltech jobs

If there is no role, or not the role you’d fit, apply anyway. Make a speculative application.

Better still, reach out to the company and / or the individual advertising the legaltech jobs or with whom you’d like to work.

Craft your elevator pitch about:

• who you are;
• what you’re looking for;
• what you bring to the table;
• why you are interested in their business / what they do; and
• why you are interested in legaltech.

Some companies actively encourage this.

For instance, Eigen Technologies does just that — see here.

We know of several lawyers who did exactly this and applied to legaltech companies little and large and had great success creating a role for themself, often a role the company didn’t know they needed!

Be bold, be brave and be yourself!

The money question: salaries

Legaltech roles vary significantly between private practice (e.g. legal innovation roles), in-house (legal ops roles) and vendor side roles (ranging from sales through to product through to software development etc). Remuneration can also vary significantly based on the individual. So read the below with this in mind!

Show me the money

The below are indicative ranges based on conversations with recruiters and industry leaders about a variety of roles and organisation types:

Org Type Low Mid High Law Firm £30,000 £75,000 £180,000+ In-house £30,000 £55,000 £100,000+ Vendor £30,000 £60,000 £120,000+

If you are entering the legaltech space for the first time, especially from a traditional legal background at a large law firm with 2–5 years experience (including training contract), a salary around the mid-range is quite possible at any one of the three types of organisations described above.

If you are a lawyer and have more experience, perhaps 1–3 years in a similar role elsewhere, you may be able to aim higher depending on the role and organisation, especially for law firm roles.

For non-legal specific expertise, e.g. product managers, developers and data scientists, higher salaries are quite possible — especially vendor side — given how in demand these skills are outside of legal, and increasingly within legal.

Other compensation

The other variables are the obvious ones such as bonuses, equity / share options and pensions etc. This is where things differ quite a bit depending on organisation type, role and the individual.

Pensions and benefits

Law firms and in-house roles may offer generous pension contributions and other benefits, e.g. subsidised gym memberships, home working equipment allowances, childcare, healthcare and so on.

Equally in-house teams and vendors may offer these types of benefits depending on their size.

Bonuses

In all cases you may secure a role with a variable bonus component, usually based on your individual performance, that of your team and / or the organisation in general.

Law firm roles tend to include bonuses, but not always. Most law firm bonuses for legaltech roles will be in the 5–15% range for innovation roles. For in-house roles, bonus elements vary widely depending on organisation type, size and industry.

Equity and share options

Where vendors differ is that they may offer equity if you are a founding member or employee 1–5 perhaps, and share options or similar long term incentives if you are a later stage employee (e.g. employee 6–10+).

The latter will usually vest over 4 years, sometimes with the election to decide a % split between those options that vest as cash (valued at the time they vest and based on the then company valuation) or shares.

Depending on the size and growth of the vendor, these can be significant. But they aren’t a guaranteed return necessarily.

For instance, if you have share options that vest as shares, those shares may be affected by future dilutions (meaning they are worth less per share even if the company increases in value) and typically can only be cashed in if the vendor is sold or IPOs, which may never happen or may happen at a much lower price than anticipated. To balance those risks, as noted above, you can often — but not always — elect to have some % vest in cash and some as shares.

Commission

Vendor roles aligned to sales or presales will often include a commission element, usually some % of each sale won by the business, and in some cases an additional % for deals closed by you individually or as part of a sales team (e.g. a salesperson and presales person might get an additional % for a deal they close).

Sometimes the % will vary depending on what the organisation wishes to sell most.

Because cloud is cheaper, easier to update and more scalable, a lot of vendors are trying to migrate existing customers to the cloud based versions of their apps (e.g. including the biggest vendors such as Microsoft). As a result, the commissions for closing these types of sales will be higher than alternatives. Likewise kickers for upselling or cross-selling additional products, features or services generates further commission.

In other words, you eat what you kill.

Sometimes there may be further commission for securing renewals or upgrades to existing customers, or moving them across to alternative license models such as monthly recurring subscriptions and so on, again because these will be attractive from a balance sheet perspective. Sometimes this compensation and responsibility sits with customer account / success managers. Their job is to keep customers happy, retain them and ensure their licences get renewed (and ideally upgraded).

Note this usually means your progression and success / fail at the role is tied to sales or similar targets, i.e. a total number and sometimes type of sales to hit each quarter and each year.

If you are, or get, good at selling (or keeping customers happy) you can make significant money all in, e.g. £150,000+ per year including base at some of the larger vendors.

The quid pro quo is that you don’t usually get paid commissions until the end of a quarter, or sometimes the following quarter after the quarter in which you closed the sale.

If your total take home package is heavily dependent on variables like commissions and bonuses it can make things like getting a mortgage or other loan trickier, i.e. because your income may fluctuate up or down significantly.

Salary progression

This is where it really is a choose your own adventure. How much and how quickly you are able to increase your earning potential and seniority within an organisation, whether law firm, in-house or vendor side will depend on luck, timing, your ability and the type of organisation and role.

Unlike a traditional legal role, there will unlikely be guaranteed / semi-guaranteed lockstep salary progressions. At most you may only be guaranteed to receive an inflation equalising, or slightly above inflation, salary uplift each year… which at current inflation rates may only be 0.5–2.5% a year.

Good luck 🍀

We hope this gives you plenty to work with. These are the routes into the sector that we find the more profitable in terms of return on investment for individuals seeking news roles in legaltech.

We hope you can find your dream legaltech job!

If we missed anything, get in touch!

⚡ Don’t forget the rest of the guide ⚡

This article forms part 2 of our 6 part series on careers in legaltech, legal ops and innovation. Please check out the other articles and career profiles for more inspiration and guidance!

Originally published at lawtomated.