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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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Prompt

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}}

Powered by Hugging Face Inference API

Pro Tips

  • The pre-mortem technique is proven to reduce overconfidence; the steel man prevents pure negativity.

References

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