These are prompts from my personal library—ones I've used regularly and found genuinely useful in my work as a product leader.
They're not theoretical. Each one has saved me time, sharpened my thinking, or helped me catch something I would have missed. I'm sharing them because the best tools are the ones that actually get used.
They work with Claude, ChatGPT, or any other AI tool you're using. Copy, paste, fill in the brackets, and go.
💡 How to use these prompts
Replace everything in [SQUARE BRACKETS] with your actual context. The more specific you are, the better the output. These are starting points — push back on the AI, ask follow-up questions, and don't accept the first answer if it feels thin. The thinking still has to be yours.
When I use it: Every time I'm looking at a potential new opportunity and I want to pressure-test it before I commit time or resources. It's good at surfacing the assumptions I'm making without realising it.
You are a rigorous product strategist. I'm going to describe a product opportunity and I want you to help me pressure-test it.
The opportunity: [DESCRIBE THE OPPORTUNITY IN 2–3 SENTENCES]
The target customer: [WHO IS THIS FOR]
The problem we're solving: [WHAT PROBLEM DOES THIS ADDRESS]
Please do the following:
1. Restate the opportunity in one sentence as a testable hypothesis
2. Identify the 3 most important assumptions I'm making that could be wrong
3. For each assumption, suggest the fastest way to test it
4. Ask me the one question I most need to answer before committing to this
Be direct. Challenge weak reasoning. Don't validate without evidence.
When I use it: When I've written a strategy or proposal and I want to find the holes before I present it. I'd rather hear the hard questions from an AI at 10pm than from a sceptical exec in the room.
You are a senior product leader tasked with finding the weaknesses in a product strategy before it goes to leadership. Be rigorous and direct — your job is to find the holes, not to be encouraging.
Here is the strategy: [PASTE YOUR STRATEGY DOCUMENT OR SUMMARISE IT HERE]
Please:
1. Identify the 3 most significant weaknesses or gaps in this strategy
2. Flag any assumptions that are doing too much work without evidence
3. Note anything that's missing — customer insight, competitive context, success metrics, resourcing
4. Give me one question a sceptical executive would ask that this strategy can't currently answer
Don't soften the feedback. I need to know what's wrong before someone else tells me.
When I use it: When I need to communicate something difficult—a delay, a cut, a pivot—and I want to make sure I'm leading with the right thing and not accidentally being defensive about it.
Help me write a clear, honest message to [DESCRIBE YOUR AUDIENCE — e.g. "senior stakeholders", "the engineering team", "the CEO"] about [DESCRIBE THE SITUATION — e.g. "a delay to our Q3 roadmap", "a decision to cut a feature", "a strategic pivot"].
Context:
- What happened: [EXPLAIN BRIEFLY]
- Why it happened: [HONEST REASON]
- What we're doing about it: [YOUR PLAN]
- What you need from them: [IF ANYTHING]
Write the message in a tone that is direct and honest without being defensive. Lead with the impact, not the explanation. Keep it under 200 words. Then tell me the one thing in this message that could land badly and how to handle it.
When I use it: After a round of customer interviews or research, when I've got a pile of notes and I need to find the signal. It's particularly good at separating what people said from what they actually seemed to need—which are often different things.