Your Next Executive Coach Might Be An AI

Seven surprisingly effective coaching AI prompts you can use right now

Some days at work, you just feel stuck.

You've got decisions piling up, a tough conversation looming on the calendar, a big opportunity you don't want to screw up… and you've got nowhere in your day to make space for the deeper reflection these kinds of asks demand.

These are the moments when a great executive coach is worth their weight in gold.

But here’s the problem. Great coaches are expensive. They're hard to vet. And frankly, even if you can find and afford one, they're not always available when you need them most.

That's why I've been experimenting with a different use case for AI: turning it into my on-demand executive coach.

First, a disclaimer: AI is far from a perfect substitute for a skilled executive coach. AI can't draw on the kind of deeper 1:1 human relationship you build over time. It can't read your body language. And it can't notice the subtle stuff—like how your tone of voice changes or what you're not saying.

But when it comes to getting clear, uncovering blind spots, or preparing for high-stakes conversations?

AI can get you 80% of the way there.

And it's available 24/7—assuming you know how to prompt it correctly.

The Coaching Framework That Actually Works

When I was building out Bain's leadership development practice, I went deep on the science of coaching. I needed a teachable framework we could use to helpo structure an "executive coaching black belt" session for senior partners at the firm.

I was looking for something clear, practical, and powerful. Something our leaders would actually use to navigate messy team dynamics or guide clients through challenging strategic decisions.

The best resource I found? Michael Bungay Stanier's The Coaching Habit.

Michael breaks down great executive coaching into a framework built on seven simple questions. Each question is designed to unlock clarity and momentum. They're easy to remember, easy to use, and (maybe most importantly) force you into a coaching posture built on curiosity, where you're pulling the answer out of the person you're coaching (versus letting your “advice monster” take over).

Michael on stage for a Ted Talk w/ one of the best guidelines for coaching I’ve ever seen: “Stay curious longer.”

We built our coaching curriculum around those seven questions. And since then, I've used them with CEOs, teammates, and on myself—before hard conversations, career decisions, and moments where I've just felt totally stuck.

And now? I'm using the same questions with AI.

Guess what? It's working.

The "AI As Executive Coach" Prompt Sequence

Here's the exact framework I use—with each coaching question paired with a ready-to-use AI prompt. Think of this like your personal executive coach, sitting quietly in your pocket, ready to go whenever you need it.

1. The Kickstart Question

Question from the book: "What's on your mind?"

AI Prompt: I'm facing [brief description]. Help me quickly outline what's truly important—and what's just noise.

Why it works: When you’re stressed, your brain wants to dump everything out on the table at once. This prompt forces you to distill down the issue you’re dealing with into the 2-3 things that actually matter.

2. The AWE Question

Question from the book: "…And what else?"

AI Prompt: Given this outline, push me to go deeper. What else might I be overlooking?

Why it works: Most of stop thinking once we reach the surface level of the problem. Your answer to the first question protects you from the harder, more uncomfortable stuff underneath. This forces you past that protective layer and invites the deeper reflection that can help you spot the real challenge or opportunity in what you’re dealing with.

3. The Focus Question

Question from the book: "What's the real challenge here for you?"

AI Prompt: Help me pinpoint the heart of this issue. What's the underlying challenge I might be missing?

Why it works: Most of what you think is "the problem" is actually just the symptoms. This cuts through the surface drama to find the thing that's actually causing everything else.

4. The Foundation Question

Question from the book: "What do you want?"

AI Prompt: Given this issue, ask me questions to help me define exactly what I want—clearly and specifically.

Why it works: You can't solve a problem until you know what success looks like. Most people skip this step, never reflect on where they’d actually like to end up at the end of their predicament, and then wonder why they keep going in circles.

5. The Lazy Question

Question from the book: "How can I help?"

AI Prompt: Knowing my goal, suggest specific ways you could help me move forward effectively.

Why it works: This shifts you from venting about the problem to actually doing something about it. It forces you to get concrete about your available options instead of spinning your wheels or just wallowing in your feelings.

6. The Strategic Question

Question from the book: "If you're saying yes to this, what are you saying no to?"

AI Prompt: If I commit to this path, what am I deprioritizing—explicitly or implicitly?

Why it works: Every decision has an opportunity cost, but we pretend it doesn't. This makes the trade-offs visible so you can decide if it’s worth it. It also helps you spot broader patterns hidden behind your desired end-state.

7. The Learning Question

Question from the book: "What was most useful for you?"

AI Prompt: Summarize the key insights from this conversation. What's the one thing I should carry forward?

Why it works: Without this step, the insights from your coaching sessions will start to evaporate as soon as you close the chat. This locks in the one thing that's actually actionable - and the one thing you can apply the next time a challenging situation pops up.

How This Actually Plays Out

Last week, I used this prompt sequence to prep for a tough 1:1 with an executive.

The issue I planned to discuss felt messy. It touched on performance, expectations, dynamics, timing, and working style. I was really struggling with how to frame things and what I might need to navigate once the conversation kicked off.

But in five minutes with ChatGPT, I had a clean outline. I was clear on what I was actually worried about, what outcome I wanted, and what I might need to say and ask to make that outcome possible.

The conversation still took work. It wasn’t easy. But the situation no longer felt chaotic or unmanageable. And while navigating it was difficult, I felt so much clearer going into it—and coming out.

That's what coaching is supposed to do.

It doesn't fix everything for you. But it does prepare you to face it.

And now? It's not a resource you have to book weeks in advance or pay an expensive monthly retainer to access.

Good coaching is now just a prompt away.

Pretty cool.

Author’s note: The more you understand the fundamentals of good executive coaching, the better you’ll be able to prompt your AI to act as your personal coach. I’d highly recommend reading Michael’s book to get a sense of “what good coaching looks like” - but if you’d prefer a quick summary, this 6 minute video does a pretty good job of outlining the main ideas in the book.

And if you’re in the market for a real live executive coach (or for broader management/leadership coaching + training for your team), I can’t recommend the team at Wind + Sail Leadership Partners enough. They’ve been awesome supporters of my portfolio companies, and deliver the kind of coaching and attentiveness AI can’t come close to delivering.