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The Habit Of Asking For Three Options, Not One

By Nigel Guy · 2 min read

Ask Claude for a name, a headline, an approach, or a solution, and it gives you one — confident, well-formed, and delivered as if it were the obvious answer. You read it, it sounds fine, and you take it, because there's nothing on the page to compare it against. The first answer isn't wrong, usually. It's just the only thing you've seen, which is a different thing from being the best available option.

The rule: ask for three genuinely different options before you judge any of them — a single answer can only be accepted or rejected, never actually compared.

The mechanism

  1. Ask for three before you ask for one good one. Not three variations on the same idea with the adjectives swapped — three that take a visibly different approach. If they all read the same, say so and ask again.
  2. Name the axis of difference up front. "Give me three options: one cautious, one aggressive, one in between" or "one that assumes I have a week, one that assumes I have a day" produces real spread. Left unguided, Claude often gives you three flavours of the same instinct.
  3. Make it argue for each one separately, in a sentence or two, before you pick. A one-line case for each option surfaces trade-offs that a bare list hides.
  4. Pick, then ask what you'd lose by not choosing the others. This is the step people skip. It's often where the actual insight is — not in the option you took, but in what the runners-up would have caught that your choice won't.
  5. Only go back to a single answer once you know what you're optimising for. After the first round of three, a follow-up request for one refined version is fine — you're no longer anchoring on the only thing you've seen.

What to skip

Skip asking for three when the request is genuinely mechanical — a regex, a date format, a one-line fix. Forcing options onto a question with one correct answer just adds noise. And skip treating the three as a menu to average together; a plan stitched from bits of all three options is usually worse than any one of them taken whole.

Guardrails

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