The most useful Ai prompt I use came from a book I read last year, Geoff Woods’ The AI-Driven Leader:
Interview me, one question at a time, to extract everything I know about [x] subject before helping me condense and make sense of it all.
That prompt has stuck with me because it flips the way we use Ai.
When I’ve have asked Ai to write a strategy, create a plan or solve a problem, I too often end up disappointed when the output feels generic, shallow or disconnected from the reality.
Strategy, for example, is not a blank-page problem. As leaders, we already have the raw material in our head: market knowledge, customer feedback, team issues, constraints, opportunities, risks and hard-won instincts. The problem is getting it out, making sense of it, and turning it into something clear enough for other people to understand and act on. That is where Ai can be genuinely useful. Not as the author of our strategy, but as the interviewer, challenger and coach that helps extract and sharpen our own thinking.
Set your Ai up properly first
Before you ask Ai to coach you on strategy, give it something useful to work with:
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Inputs: your current plan, vision, values, templates, meeting notes, customer insights and leadership feedback.
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Instructions: the role, behaviours and rules that tell Ai how to operate.
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Outputs: the plans, summaries, drafts and artefacts it creates with you.
For example:
You are my business strategy coach. Help me clarify my thinking, challenge my assumptions, identify gaps, and turn my ideas into a practical strategy my team can understand and execute. Ask one question at a time. Be direct, skeptical and practical.
Teach it how you like to be advised
Ai can be too agreeable by default, so tell it exactly how you want to be coached.
When you advise me, be direct and practical. Do not use corporate fluff. Do not over-praise my ideas. Challenge weak assumptions. If something is vague, ask me to be more specific. If I am avoiding a hard choice, point it out. Treat me like a capable leader who wants honest advice, not reassurance.
A useful strategy prompt sequence
Once your Ai is set up, the process can be surprisingly simple.
Start with extraction.
Extract: Interview me one question at a time to understand my business strategy. Do not move on until you fully understand each answer. Once you have enough context, summarise what you have heard and identify the main strategic themes.
Then ask it to challenge you.
Challenge: Now act as a critical business coach. What are the gaps, contradictions, weak assumptions or unresolved choices in what I have told you? Be direct.
Then stress-test it.
Stress-test: What are three ways this strategy could fail? What would a competitor, customer, or disengaged team member see that I might be missing?
Then simplify it.
Simplify: Take everything I have shared and distil it into a one-page strategy summary a new employee could understand in five minutes.
Then articulate it.
Articulate: Turn this strategy into a clear narrative: where we are now, where we are going, why it matters, what choices we are making, and what we need from the team.
Then reframe it.
Reframe: Present this strategy back to me in three different ways: one for the board, one for the leadership team, and one for the broader business. Keep the core message consistent but adjust the emphasis for each audience.
Then look for blind spots.
Uncover blind spots: Based on everything I have told you, what have I not mentioned that I probably should have? What questions have I avoided answering?
None of these prompts replace the leader.
They force the leader to think.
The real value is not the answer
Do not use Ai to avoid doing the thinking. Use it to make the thinking harder to avoid. Because most of the time, your strategy is already in there somewhere. You just need a better way to extract it, challenge it, sharpen it, and explain it.
The best strategy session I have had with Ai did not feel like asking a robot to tell me what to do. It felt like having a patient, relentless interviewer sitting across from me, asking the next useful question and refusing to let me hide behind vague thinking.