COACHING TIPS FOR ADVISORS TO BUSINESS OWNERS
Recent Advisor Articles:
ExitMap Coaching Tips for Working with Business Owners
by John F. Dini, CExP, CEPA, CBEC, The Exit Planning Coach®
The Personal Expenses Trap: How Business Owners Accidentally Destroy Their Own Value
Ask a business owner what their company is worth, and you’ll get a number. It will be stated with confidence. It may have been repeated to a banker, included on a personal financial statement, and factored into a retirement projection prepared by a well-meaning financial planner. There is a reasonable chance it is wrong by fifty percent or more. That is not an exaggeration, and it is not the owner’s fault. They simply don’t have access to the information needed to make an accurate assessment. But when you build a retirement plan around a number that isn’t real, the whole plan is built on sand. When 80 Percent of Net Worth Is Guesswork – In my experience working with business owners over the course of decades, it is[…]
The Exit Planning Coach™ also produces a bi-weekly podcast for advisors specifically focused on marketing trends, business owner engagements and life after the business. Each episode features an interview with a professional in the exit planning industry. Get more Tips for Advisors here.
CATCHUP WITH OUR LATEST RELEASE!
The Exit Planning Coach™ Handbook: A Guide for Advisors to Business Owners
by John F. Dini, CMBA, CExP, CEPA
The Exit Planning Coach™ Handbook is for every advisor who works with business owners. It describes why coaching before the sale is necessary, how working with owners is different than counseling other executives, and lays out the steps of coaching discovery that help to bring owners to better outcomes for the most important financial transaction of their lives.
Available now on Amazon in the Kindle Store, in paperback and soon as an audiobook.
The Business Owner’s Balance Sheet: What Your Financial Planning Software Isn’t Telling You
Ask a business owner what their company is worth, and you’ll get a number. It will be stated with confidence. It may have been repeated to a banker, included on a personal financial statement, and factored into a retirement projection prepared by a well-meaning financial planner. There is a reasonable chance it is wrong by fifty percent or more. That is not an exaggeration, and it is not the owner’s fault. They simply don’t have access to the information needed to make an accurate assessment. But when you build a retirement plan around a number that isn’t real, the whole plan is built on sand. When 80 Percent of Net Worth Is Guesswork – In my experience working with business owners over the course of decades, it is[…]
The 3% Problem in Advisory Work
Business owners represent only 3% of the population, yet many advisors approach them with the same frameworks they use for executives, other professionals, or retirees. That’s the first mistake. Owners are not simply high-income individuals with a concentrated asset. They are decision-makers whose livelihood, identity, and daily purpose are tied to something they built. Their company is not an investment allocation. It is the source of their authority, reputation, and regular pops of dopamine. When you advise a traditional client, you are often optimizing around assets. When you advise a business owner, you are navigating their identity. Those are very different conversations.[…]
For the owners of a privately held business, disclosure in a sale process is about layers of disclosure, not just a checklist exercise. It is a sequencing discipline. The timing, depth, and framing of information release can materially affect valuation, negotiating leverage, and— although often overlooked—the stability of the business during a prolonged transaction. Advisors are uniquely positioned to help owners understand that disclosure should expand only as buyer commitment, legal protection, and deal certainty increase. What follows is a practical framework for guiding that progression. Early-Stage Disclosure – The objective of early[…]
Exit Planning: If Not Now; When?
The most common response advisors hear from owners is some variation of “Talk to me in five years.” Exit planning is cognitively demanding and therefore easy to defer, even among sophisticated entrepreneurs. Owners rarely lack reasons. They are focused on growth, not departure. They assume circumstances will change. They are confident buyers will emerge if the business performs well. They expect continuity through family or employees. Some believe that, if the exit is executed correctly, the financial outcome will render the rest irrelevant. Collectively, these rationales make delay feel prudent rather than avoidant.[…]
The Advisor’s Biggest Challenge
Advisors’ biggest challenge isn’t giving advice. It’s what they do with that advice. Advisors give advice—that’s kind of the deal, right? Business owners reach out because they want to understand something they don’t already know. You walk into the first meeting knowing there’s an expectation that you can contribute some smarts to whatever issue they’re facing. Beware of Being a Hammer – To a hammer, everything is a nail. I often use the analogy of a medical practice. A patient goes to a doctor and says, “Doctor, my shoulder hurts terribly. I can’t stand it anymore. Can you help me?” Of course, that’s why the doctor studied[…]
NQDCs – “Funding and Forfeiture”
In our last article, we discussed Non-Qualified Deferred Compensation (NQDC) plans as a tool to compensate key employees for achieving long-term goals. One component of such plans is the fact that they are frequently unfunded and legally considered an unsecured promise to pay. Nonetheless, both plan sponsors and recipients often want a funding mechanism to set aside assets, manage cash flow, or hedge the liability. In addition, employers typically want conditions under which they can rescind the plan for cause, including failure to achieve the objectives[…]
NQDCs – “Let Me Count the Ways”
Non-Qualified Deferred Compensation (NQDC) plans are a powerful tool for incentivizing and retaining key employees. They offer virtually unlimited flexibility in methodologies, objectives and rewards to suit a company’s strategies and goals. What is “unqualified?” Quite simply, NQDCs are discriminatory. Some owners shy away from that term, but discrimination isn’t automatically illegal. Illegal discrimination in the workplace is when an employer or manager treats an employee unfairly due to their race, color, religion, sex, national origin, age[…]
How Much does the Big Picture Count?
It is currently difficult to have a business conversation without discussing the Big Picture. The voracious 24-hour news cycle needs plenty of fodder to attract eyeballs. It almost seems like the media must pick and choose what will create the most concern. “Seventeen dead in drone attacks? Let’s put that sixth on the schedule.” Big Picture Issues – Wars in Ukraine, Israel, and Sudan. Attacks on shipping. Russian hacker ransomware. The battle between the U.S. executive and judicial branches. Tariffs, sanctions, inflation, interest rates, boycotts[…]
According to surveys by both the Exit Planning Institute (2013) and PwC (2021), 75% of business owners are either “unhappy” or “profoundly unhappy” one year following their exit from the business. For a number that is so dramatically unfavorable, why hasn’t the entire industry adjusted to address this issue in nearly a decade? In this article, we will examine why so many business owners are unhappy and what advisors should be doing to rectify the situation. Anyone who works regularly with business owners understands the bond between owners […]
The concepts of rights and freedom are inextricably intertwined. When we discuss freedom as a concept, it usually centers around the idea of rights. The Magna Carta of 1215 documented that the rule of law and due process applied to everyone (except, of course, women and the enslaved). It is the basis for all constitutional forms of government. For business owners, the notion of freedom is often tied to the ability to control their own destiny. In interviews with hundreds of business founders, we’ve found that this desire consistently ranks among the[…]
Findings from the 5th Annual Exit Planners Survey
Between February 1 and March 2, 2025, ExitMap conducted its annual survey of exit planning professionals. The report offers a comprehensive overview of this rapidly growing sub-industry and stands as the only study that spans multiple professional specialties. To gather insights, the survey asked 30 questions of 7,267 advisors who either hold a recognized certification in exit planning, participate in an exit planning professional organization, or advertise as specialists in the field. We received 434 responses representing eight specialties in six[…]
One of the most frequent sales techniques of value enhancement advisors is the “planning fallacy.” It goes like this: “I’ve examined your company and believe it is worth $4.2 million. There is a value gap between what it is worth today and what it could be worth. With proper planning, it could be worth as much as $7.7 million. Would you rather exit with $4.2 million or $7.7 million?” Of course, that’s a trick question. No entrepreneur would respond with the lower number, if only not to appear foolish.[…]
“I’m taking the logos off my trucks. It just makes them a target for personal injury lawyers. I don’t want to put our newest product innovations on our website. The competitors just copy them. We are creating a human resources LLC so that employees are segregated from the rest of our business. This gives us some safety from spurious claims. We pay all of our employees to bring their vehicles back to the yard every night. We don’t want to be responsible for what they do on their own time. We were thinking of opening a new location, but the news says the economy is going to take a dip. I thought about hiring another salesperson, but I can’t be sure they will pay for themselves.”[…]
Your client’s business is doing pretty well. He adds to his personal savings every month and is far more concerned about tax savings on his profits than making payroll. What are indicators that he may not be maximizing opportunities? Some indicators are obvious, while others are less so. One of the easiest to identify is stagnation. Businesses are like organisms—they either grow or die. Flat or declining sales are inherently unhealthy, as they limit opportunities for top[…]
There’s a difference between goals and resolutions. Businesses set goals; they can be budgetary, operational, recruiting, sales, or profit-oriented. Individuals make resolutions. Business Goals – Goals are focused on a particular outcome and should be specific. It’s always worth the time to get into the details. How will you increase the company’s cash flow? If it’s by boosting sales, what has to change to make that happen? You could add a new product line, enter[…]
Financial planners use the term “holistic planning” frequently. It’s meant to indicate that they consider the client’s short- and long-term life goals and the future they visualize. According to Fidelity Investments, holistic wealth planning is continuous and considers two dozen aspects of client wealth objectives. Only one of those is a business. This raises the question “If a typical business owner has 50%”[…]
Occasionally, we run into what I call “Battling Assets.” That is when an owner is drawing a comfortable income from the business, but it is arranged in a way that denigrates the business value, the value of the asset, or both. Here are three case studies of “battling assets.” Under-optimized Real Estate – Two partners operated a beautiful campground. The acreage was along a river, and despite rapid suburbanization in the area, the bluff on the opposite bank prevented any[…]
Technology Costs and Quality of Earnings
Are you avoiding technology costs? A few months ago, an ExitMap® subscriber called with a tech support issue. “Your software doesn’t work,” he said. After some investigation we identified the problem. He was using a version of the underlying engine, (a part of Microsoft Office) that was four or five generations past end-of-life. When asked about his willingness to upgrade he said, “I don’t want to be[…]
Normalizing cash flow is done with the intention of identifying Earnings Before Interest Taxes Depreciation and Amortization (EBITDA) or Seller’s Discretionary Earnings (SDE). These differing measures of free cash flow are not interchangeable but are used by different classes of buyers for different categories of acquisition.[…]
We began this three part series by saying that Private Equity’s reputation is a “Great Satan” to some, and a “Savior” to others (depending on the personal experience of the speakers). In fact, both reputations are well deserved, but neither can be universally applied. The “Great Satan” Private Equity Reputation – PEGs buy companies for the express purpose of improving their performance.[…]
Private Equity Leverage and Interest
In our previous article we discussed the general structure of Private Equity, how it works and the types of Private Equity Groups (PEGs). They have grown rapidly as an alternative investment that produces far better returns than Treasury Bills or publicly traded equities. The Power of Someone Else’s Money – How do they provide these enviable 18% to 25% returns on an investment?[…]
Private Equity and Privately Held Businesses
Depending on who you are talking to, Private Equity is either the Great Satan or the Blessed Savior of small and mid-market companies in the United States. Of course, the stories that are told depend a lot on the personal experience of the speakers. Once a vehicle for high-risk investment plays in corporate takeovers (see Bryan Burrough’s Barbarians at the Gate), Private Equity has morphed[…]
The State of Exit Planning 2024
We just finished our analysis of the 2024 Exit Planners Survey (2023 Industry Activities). We polled almost 6,000 practitioners, received over 400 completed surveys, which means the data has a confidence level of 99% with a 6% margin of error. One notable finding from the survey is that exit planning advisors reported a slight decrease in client inquiries and engagements compared to previous[…]
U.S. Business Owners: The Surprising Statistics – When it comes to careers, business owners are a small minority of the population. In conversations this week, I mentioned the statistics several times, and each owner I was discussing it with was surprised that they had so few peers. According to the Small Business Administration (SBA), there are over 33,000,000 businesses in the US.[…]
Addressing the Value Gap: Truth in Pricing
Truth in pricing is a common issue when discussing the sale of a business. The selling price of their company is a point of pride for any owner. When they are willing to share the price they were paid, they usually include everything listed in the purchase agreement. While there is nothing inherently dishonest about that, it’s often not exactly the truth either.[…]
Addressing the Value Gap: Living Expenses
What is a Value Gap? The Value Gap is one of the most used phrases in exit planning. Simply stated, it’s the difference between what a business owner would realize if he or she sold the company today, and what they need to embark on a financially secure “next act” after business ownership. Both amounts can be determined with some accuracy by professionals.[…]
Personal Vision and Life After the Sale: Part III
Purpose – “Having as one’s intention or objective.” Many exit planning advisors discuss the three legs of the exit planning stool – business readiness, financial readiness and personal readiness. In our previous two articles we focused on two of the “big three” components of a successful life after the sale, activity and identity. The third is purpose.[…]
Personal Vision and Life After the Sale: Part II
In our last article about life after the sale we focused on identity which is only one of three important considerations. Purpose and activity also play major roles in an owner’s personal vision. Even a business owner who is comfortable with “who they are,” still needs to address the nuts and bolts associated with activity. A business owner spends 20, 30 or (not uncommonly with Boomers) 40 years[…]
Personal Vision and Life After the Sale: Part I
Life after the sale is often both the most important and most neglected factor in exit planning. According to two different surveys in 2013 and 2022, 75% of owners report regrets or unhappiness a year after transition. However, exit plans continue to be constructed primarily around financial targets. In the event you haven’t heard this since you were five years old, “Money doesn’t fix everything.”[…]
Lifestyle or Legacy? Looking at two very different types of owner transition objectives
When preparing for the transfer of a business, there are many stakeholders who can impact the plan, including owners, employees, family, investors, customers, regulatory agencies, and successors. Some have direct authority or decision-making capability over the transaction. In general, it’s best to presume that anyone who has a relationship with the owner or the business will have some influence on the decisions impacting the transfer. […]
Exit Planning and Stakeholders
When preparing for the transfer of a business, there are many stakeholders who can impact the plan, including owners, employees, family, investors, customers, regulatory agencies, and successors. Some have direct authority or decision-making capability over the transaction. In general, it’s best to presume that anyone who has a relationship with the owner or the business will have some influence on the decisions impacting the transfer. […]
Exit Options: The Road Less Traveled
The road less traveled is often a misimpression when considering a transition from business ownership. Surveys show that roughly 85% of owners expect their exit to happen via sale of the business to a third party. A third-party sale is certainly attractive. The idea of monetizing decades of work in one lump-sum payoff seems equitable. Years of sacrificing to “invest in the business” is supposed to generate a return. “He (or she) sold the company” […]
What is the Value of Certification?
We’ve just released the 2023 National Exit Planner Survey (NEPS). This is the third year for the survey, and participation continues to increase. This year we were able to reach a 99% confidence level in the result, with only about a 2.5% margin of error. Currently, this is the ONLY survey of exit planning advisors in North America. However, a number of organizations survey business owners regarding their exit planning. […]
Does AI Have a Role in Exit Planning?
The media is packed with stories about Artificial Intelligence. According to the stories, because a smart search engine (essentially a Learning Language Model [LLM]) can pass a Bar exam, it threatens all kinds of white collar careers. In case you are wondering, no – I’m not writing this on ChatGPT. That “surprise” trope has been so overdone on every local television station, I hope I never see it again. Also, if you thought this column would be about how to write letters, […]
Company Readiness: Delegation and Management Depth
For many business owners, exit planning means getting the company ready for a sale to a third party. There are a number of approaches to enhancing preparedness for a third-party sale. You need to understand their current level of preparedness to effectively begin the planning process. Some planning software products begin with a comprehensive survey of the owner’s impressions of readiness. Note that we say “impressions.” […]
Defining the Role of the Coach
When an advisor chooses a coaching role, they may be venturing outside of their normal comfort zone. It may also be outside the client’s expecations of the role that has characterized the relationship up to this point. Defining the role of the coach in the client’s mind doesn’t just happen. Like any other aspect of consulting, you need to set expectations up front. The Seven Basic Rules – It’s one thing to say that you are a coach, and another to act like it. […]
The Pepperdine Private Capital Markets Survey canvasses intermediaries who sell privately held Main Street and mid-market companies. When they ask about the obstacles that prevent the sale of a business, the number one response is, “The owner’s unreasonable expectations of value.” Valuation is a sensitive subject. Some owners feel that because they worked in the business […]
The GAAP Trap
When a client sells a company to a third party, the transaction is commonly memorialized by a Purchase Agreement. That agreement contains certain representations (or “reps”) and warranties. Some of the reps and warranties are standard in such agreements, and should pose no problem to someone who has operated a good business. It is assumed that Accounts Receivable represents money that is actually owed to the company. […]
Dad’s (or Mom’s) office is often perceived as the center of authority by employees and other family members. It’s where you got called on the carpet, where you were informed of promotions, or where you took on an insolvable problem.
When a parent/CEO is handing off operating responsibilities, there is often a lag, sometimes measured in years, between stepping back from the daily decisions and completely separating from the premises. […]
Are You Preparing Your Clients for 2023?
What does a recession mean for business owner clients who are approaching, at, or already beyond normal retirement age? It has become fashionable to pontificate about the “inevitable” recession coming next year. Although there is an argument for not talking ourselves into making it happen, there are indisputable reasons why it is going to occur regardless of whether we discuss it or not. […]
Exit Strategy – Harvest or Grow?
In every internal transfer, whether to family or employees, the owner/seller has to make the harvest or grow decision. If the company has already reached a substantial level of success, an owner may be tempted to maximize cash flow until their departure. Deliberately reducing cash flow by starting a process of equity transfer may not sound very appealing. Owners often say, “Why would I sacrifice my personal income in order to finance their acquisition of my company?” […]
“Two Timing” is not typically complimentary. It describes a betrayal of trust – someone who is engaged in parallel relationships, usually without the knowledge of either of the other people that are involved. In the case of an exit planning engagement, attention should be given to two times, perhaps better described as two time frames. The first is when the owner wants to be free from the day-to-day obligations of running the business. The second is when they want to walk away from the company forever. […]
Two “Good” Obstacles to Exit Planning Implementation
When advising business owners, it’s vital to understand their attachment to the business. An advisor spends a lot of time developing the vision for life after ownership. Yet no matter how well developed that vision is, it isn’t unusual to find owners who behave in a way that ultimately sabotages the plan. […]
Entrepreneurs Don’t Have Rearview Mirrors
From the day they founded or assumed control of their company, the business owner has set targets and achieved them. They know how to define a goal and make it happen. They can’t tell you what happened in the past because they can’t focus on a target that’s behind them. Check your knowledge […]
Anyone selling life insurance or funeral pre-planning knows that you don’t start a conversation with, “So, let’s discuss what happens when you DIE.” For business owners, discussions about leaving the business can be as emotional as those about death. Check your knowledge […]
Understanding Main Street and Middle Market Companies
A common area of confusion among advisors is understanding the difference between a “Main Street” business, a “Middle Market” business and a “Mom and Pop” business. Check your knowledge […]
Contingency vs. Continuity Planning
When business coaches talk about preparing for unforeseen problems, they frequently commingle the terms contingency and continuity. The terms are not synonymous, and there are important differences between them. Check your knowledge […]
