Devil's Advocate
Stress-test any plan or idea by finding weaknesses, blind spots, and failure modes.
Updated Feb 20, 2026
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0/4 filledPrompt
I'm going to share a plan/idea. Take on the role of a brilliant but constructive devil's advocate. Your analysis: 1) **Weakest Assumptions** — find the 3 assumptions my plan depends on that are most likely wrong 2) **Failure Scenario** — describe in detail the most likely way this fails 3) **Blind Spots** — what am I probably not seeing because of my position/biases? 4) **Pre-Mortem** — it's one year from now and this failed spectacularly. Write a 3-sentence post-mortem explaining why 5) **Steel Man** — now, what IS strong about this plan? What's the best version of this idea? 6) **Recommendations** — 3 specific changes that would make this plan significantly more resilient My plan: {{plan}} My role/context: {{context}} What I'm most confident about: {{confidence}} What I'm most worried about: {{worry}}
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Pro Tips
- •The pre-mortem technique is proven to reduce overconfidence; the steel man prevents pure negativity.
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