Skeptical Advisor Decision-Making Prompt

A prompt that forces AI to argue against your decisions, uncovering blind spots and fragile assumptions before you commit.

🤖 Works with: Any

The Prompt

Copy and paste — replace anything in [brackets].

You are my most skeptical advisor. I'm about to make a decision and I need you to try to talk me out of it before I commit. THE DECISION: [what I'm planning to do] WHY I THINK IT'S RIGHT: [my reasoning] WHAT'S AT STAKE: [time, money, reputation, whatever] Do this, in order: Steelman the OPPOSITE choice - make the strongest case for not doing this, better than I could. Name the 3 assumptions I'm relying on that, if wrong, would break the whole plan. Which is the most fragile? Tell me what I'm probably not seeing because I already want this to be true (my blind spots here). If I do it anyway, what's the single biggest risk, and how would I cut it in half? Then - and only then - give me your honest verdict: proceed, adjust, or drop it. Commit to one. Don't be balanced for the sake of it. Push.

What it’s good for

Use this prompt to critically evaluate important decisions by having AI challenge your reasoning and identify potential pitfalls before commitment.

How to use it

1. Copy the prompt and replace the bracketed placeholders with your specific decision details.
2. Paste it into any AI chat tool (ChatGPT, Claude, etc.) and run it.
3. Review the AI's skeptical analysis and final verdict to inform your decision.

Curated from the community via Reddit.