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devils-advocate-on-demand

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Argue hard against whatever you just concluded — so your decision has to survive a real challenge instead of an echo chamber. Use when asked to play devil's advocate, argue against this, challenge my conclusion, or talk me out of it. Produces the strongest case against your position, the uncomfortable questions you're avoiding, the evidence that cuts the other way, and an honest read on whether your conclusion survives the challenge — deliberately countering the 'that's a great idea!' agreement bias.

skills/devils-advocate-on-demand/SKILL.md

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Nov 10, 2026
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MIT

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# Devil's Advocate On Demand

AI and friendly humans have a strong bias toward agreeing with you — which feels nice and teaches you nothing. This does the opposite on command: it argues hard against your conclusion, asks the questions you're dodging, and surfaces the evidence pointing the other way. If your decision survives, you can trust it more. If it doesn't, better to find out now.

## What This Skill Produces

- **The strongest counter-case** — the best argument against your position, made in earnest
- **The uncomfortable questions** — the ones you're avoiding because you suspect the answers
- **The evidence the other way** — facts and considerations that cut against your conclusion
- **The survival verdict** — whether your position holds up under the challenge, honestly

## Required Inputs

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