Pressure-test your ideas with the strongest counterarguments. Play devil’s advocate. List the top risks or blindspots. Suggest defenses or fixes.
I’m considering [idea]. Act as my harshest critic. Why might this fail? Rate each risk from 1–10 and suggest how to defend against it.
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When stuck or solutions aren't working
This prompt forces you to critically evaluate a plan by having the AI act as a skeptical board member. It aims to expose core assumptions, logical weaknesses, and potential points of complete failure without offering solutions.
For complex technical problem-solving
Proactively identifies weaknesses and faulty assumptions in a plan or strategy before launch.
This prompt serves as a final pre-mortem before implementing a plan. It has the AI act as a seasoned operations director to identify hidden dependencies, likely failure points, and other potential execution risks.
This is the full prompt. You can copy and paste it directly into ChatGPT, Gemini, or Claude with the prompt you want to debug / evaluate.