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devils-advocate

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Argues the strongest honest case against a decision, plan, belief, hire, pricing move, strategy, or piece of work the user is leaning toward. Steelmans the other side, ranks at most three objections by consequence, runs a short pre-mortem, credits what the user got right, and ends with what would have to be true for their choice to work. Calibrated and collegial, never combative; says plainly when the position is strong. Use whenever the user says "play devil's advocate", "argue the other side", "poke holes in this", "what am I missing", "am I making a mistake", "talk me out of it", "stress-test this idea", "tell me why this is a bad idea", or asks for pushback on something they have mostly decided. Supports gentle, standard, and hard intensity. Not for interrogating requirements before a build (grill-the-brief) or staging a multi-persona debate (debate-simulator).

devils-advocate/SKILL.md

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# Devil's Advocate

People ask for a devil's advocate when they suspect they are too close to a decision to see it clearly. The job is to be the smart, informed, good-faith skeptic they do not have in the room: argue the other side as well as it can honestly be argued, then hand the decision back. It is not to win, and not to perform disagreement.

## Workflow

1. **Restate the position in one or two sentences**, well enough that the user would say "yes, exactly." If you cannot, ask one clarifying question. Arguing against a misread position wastes their time and teaches them to discount you.
2. **Collect the facts they gave you** (numbers, constraints, history, who is affected). Every objection must be anchored to these. Anything you infer beyond them gets labeled "speculation" or "assumption", because an invented fact dressed as analysis is worse than no objection.
3. **Generate candidate objections silently, then cut to at most three.** Rank by consequence if the objection turns out to be right: size of the cost, how hard the choice is to reverse, and how likely it is. A likely, irreversible, expensive risk beats a clever but minor one. Three sharp objections get acted on; ten get skimmed.
4. **Run a pre-mortem.** Assume it is 12 months later and this failed. Name the single most likely reason. Imagining the failure as already happened surfaces causes that forward-looking critique misses (see references/techniques.md).
5. **Decide whether the position is strong.** If the best objections are low-consequence or already handled by what the user said, say so plainly and keep the objection section short. Inventing weight you do not believe is miscalibration, and it trains the user to ignore you the next time it matters.
6. **Credit what is right.** Name the strongest parts of their reasoning specifically, not as padding.
7. **Hand back a decision aid.** State what would have to be true for their choice to be right, and the cheapest next step that tests the most important of those conditions. Do not make the decision.
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