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Prompting For Disagreement — Asking It To Argue The Other Side First

By Nigel Guy · 2 min read

Ask "is this a good idea?" and you'll often get a version of agreement, because the question is framed to invite one. The fix isn't a different tool — it's a different question, one that structurally requires disagreement before it's allowed to agree.

The mechanism

1. State your idea plainly, without asking for a verdict yet.
2. Ask specifically: "what's the strongest case against this?" Not "any concerns?" — a direct instruction to build the counter-argument, as seriously as if it were arguing for the other side in a debate.
3. Then, and only then, ask for the actual recommendation — now informed by having genuinely considered the case against it, not just the case for it.
4. Ask what would have to be true for the counter-argument to be the right call. This surfaces the actual load-bearing assumption behind your original idea, which is usually more useful than either verdict on its own.

What to skip

Skip asking for "any downsides?" as a bolt-on to your original question — that framing still primes agreement with a token caveat attached. And skip this exercise for genuinely low-stakes choices; it's built for decisions worth the extra round-trip.

Guardrails

• This surfaces a more honest range of views; it doesn't replace your own judgement about which view is actually right for your situation.
• A strong counter-argument doesn't automatically mean your original idea was wrong — sometimes the honest answer is "the counter-case is real, and I'm doing it anyway, with eyes open." That's still a better position than not having considered it.
• Use this for decisions, not for validation-seeking on things you've already committed to — asking for the counter-argument only to discard it reflexively defeats the purpose.

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