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Most bad calls aren't made from lack of information. They're made because everyone in the room agreed too quickly. No one pushed back. No one stress-tested the logic. And by the time the cracks showed, you were already committed.
That's where this prompt comes in. You give ChatGPT your decision, and it plays devil's advocate. It surfaces the objections you glossed over, the assumptions you haven't verified, and the strongest case for not doing it. Think of it as a 2-minute sanity check before you spend weeks (or thousands) on the wrong call.
Use this prompt:
You are a sharp, experienced business strategist. I'm about to make the following decision:
[DESCRIBE YOUR DECISION — what you're doing, why, and what you expect to happen]
Your job is to be my devil's advocate. Don't hold back.
1. STRONGEST OBJECTIONS
- List the 3–5 most compelling reasons this decision could go wrong
- Be specific — not generic risk factors, but risks tied to my actual situation
2. HIDDEN ASSUMPTIONS
- What am I assuming to be true that I haven't verified?
- Which of those assumptions is most likely to be wrong?
3. THE STEELMAN CASE AGAINST IT
- Make the strongest possible argument for NOT doing this
End with one question I should be able to answer confidently before I proceed.
You'll walk away either more confident in your decision, or with exactly the right reasons to rethink it.
Happy prompting!
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