AI for beginners

I found myself repeating these five tips whenever friends getting started with AI asked me for advice. I hope they save you some time, and feel free to pass them on to friends who are new to AI.

1. Give it loads of context (using a voice prompt)

Most people ask AI a short question and get a generic answer. Instead, give it far more context than feels necessary.

If you’re planning a trip, don’t say:

“Plan me a week in Japan.”

Tell it what you liked last time, what you hated, your budget, who you’re traveling with, how fast you like to move, and anything else that might matter.

You don’t need to write a perfect prompt. Ramble. AI handles spelling mistakes, tangents, unfinished thoughts, and messy context well.

I use Handy, a dictation app for macOS, for this. I tap a shortcut to start recording, talk for a minute or two, and drop the messy transcript straight into ChatGPT, Claude, or Perplexity.

The more real context you give it, the less it has to guess.

2. Understand sycophancy

Sycophancy is AI’s tendency to agree with you and tell you what you want to hear. You might suggest an idea and immediately hear:

“That’s a great idea.”

Maybe it is. But AI can pick up your framing, reward your confidence, and make weak ideas sound stronger than they are.

Sometimes you need encouragement. Other times you need an objective answer. Don’t mistake enthusiasm for objectivity.

3. Red-team the plan

Once you have a plan you like, ask AI to attack it.

The term “red team” comes from the military. One side plays the opposition and tries to find weaknesses in the other side’s plan. You can say:

“Red-team this.”

Or, more directly:

“Stop helping me prove this is a good idea. Try to prove it’s a bad one.”

Ask it what’s weak, missing, overly optimistic, or likely to go wrong. This is one of the best checks on AI’s tendency to agree with you.

4. Ask another AI

For bigger decisions, I often copy the finished plan into another AI and say:

“A friend gave me this plan. What do you think?”

That gives you a fresh perspective without the momentum and context of the original conversation. Ask what’s missing, what could go wrong, and which assumptions look weak.

Then paste that critique back into the original conversation and let it respond. One or two rounds like this can noticeably improve a plan.

5. Reverse-engineer what worked

Sometimes it takes ten messages to finally get the answer you wanted. When you get there, don’t leave yet. Ask:

“What should I have asked you at the beginning to get much closer to this result?”

Then save that prompt, or at least notice how different it is from where you started. This is one of the fastest ways to get better at prompting because you’re learning from your own real examples.

Treat the first answer as a draft

Don’t treat the first AI response as the final answer. Treat it as a draft, the second response as a critique, and the real world as the final check.

Try it on your next real question: record a two-minute voice prompt, then ask the AI to red-team its own answer.