7 Claude Prompts to Challenge Your Reasoning

Everyone stress-tests a big decision after they've already made it. These 7 prompts make Claude argue against you before you commit: Prompts like these land here every morning. Follow @agentprompts.

1. The Steelman Opposition

   Act as the smartest person who disagrees with me. Argue the opposite of my position as well as it can possibly be argued, using my own evidence where it supports you. Do not soften it, do not hedge, and do not agree with me at the end. Finish by naming the single assumption of mine that, if wrong, collapses my entire case.

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2. The Pre-Mortem

   Act as a risk analyst. Assume it is eighteen months from now and this decision failed badly. Write the story of how it failed: the first warning sign everyone ignored, the assumption that broke, the moment reversing course became expensive, and who saw it coming. Then list the three early indicators I should be watching from next month.

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3. The Reversibility Test

   Act as a decision architect. Sort this decision into reversible or one-way, and justify it. Tell me what it would cost in money, time, and reputation to undo in three months, which parts can be tested cheaply first, the smallest version of this I could try, and how much more information a two-week delay would actually buy me.

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4. The Hidden Cost Audit

   Act as an economist. List everything this decision costs beyond the obvious price: the options it closes off, the attention it consumes for the next year, the obligations it creates, the people it commits me to, and the alternative I am giving up. Then name the cost I am most likely underestimating and explain why people usually underestimate it.

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5. The Bias Check

   Act as a behavioral scientist. Examine how I described this decision and identify where my reasoning is bent: sunk costs, wanting to be consistent with something I said publicly, overweighting a recent event, seeking evidence that agrees with me, and confusing effort with progress. Quote the words that reveal each one and rewrite them neutrally.

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6. The Decision Record

   Act as my chief of staff. Write the record of this decision so future me can judge it fairly: what I chose, the reasoning, the three assumptions it rests on, what I expected to happen and by when, what would count as evidence I was wrong, and the date I review it. Keep it to one page in plain language.

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via @agentprompts.ai

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