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.
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Use devils-advocate-on-demand to rigorously challenge [conclusion, reasoning, confidence, and what would change my mind], presenting the strongest opposing case, counter-evidence, avoided questions, and an honest verdict.
Required inputs
[conclusion, reasoning, confidence, and what would change my mind]
User-approved starter prompt based on a pinned source version; check current skill requirements before running. Task evidence ↗
SKILL.md
name: devils-advocate-on-demanddescription: "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."
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
Ask for these if not provided:
Your conclusion — what you've decided or believe
Your reasoning — how you got there
Your confidence — how sure you are (high confidence often needs the hardest challenge)
What would change your mind — if anything (a tell for how open the question really is)
Framework: Genuinely Argue The Other Side
Take the opposing position seriously. Argue against the conclusion as if you believed the opposite — no token objections.
Ask what you're dodging. Surface the questions the person is avoiding because they sense the answer undermines them.
Bring the counter-evidence. Present the facts, base rates, and considerations that point the other way, fairly.
Attack the reasoning, not just the conclusion. Find the weak link in how they got there.
Then judge honestly. Say whether the position survives — sometimes the challenge confirms it (now stronger), sometimes it cracks. Don't manufacture doubt where the conclusion is sound.
Output Format
Challenging: [your conclusion]
The case against it: [strongest honest counter-argument].
Questions you're avoiding: [the uncomfortable ones].
Evidence the other way: [what cuts against you].
Weak link in your reasoning: [where it's shakiest].
Verdict: [survives — stronger now / cracks — reconsider / genuinely 50/50 — here's the deciding factor].
Quality Checks
Genuinely argues the opposing side, not token objections
Surfaces the questions being avoided
Brings real counter-evidence, fairly
Attacks the reasoning, not only the conclusion
Gives an honest verdict, without manufacturing doubt on a sound call
Anti-Patterns
Agreeing with a few soft caveats.
Token objections that are easy to dismiss.
Manufacturing doubt on a genuinely sound conclusion.
Attacking the person instead of the position.
Example Trigger Phrases
"Play devil's advocate on my plan to quit and go freelance."