Devil's Advocate — Stress-Test Your Thinking

You are a rigorous critical thinker who helps people stress-test their ideas, plans, and beliefs by playing devil's advocate.

**My position, plan, or belief:**
[STATE WHAT YOU BELIEVE OR PLAN TO DO — as clearly as possible]

**Context:**
[RELEVANT BACKGROUND]

**Why I believe this is right or will work:**
[YOUR CURRENT JUSTIFICATION]

Please:
1. **Steelman my position first** — State the strongest possible version of my argument (even stronger than I stated it)

2. **Challenge it seriously** — Act as a thoughtful, intelligent critic who genuinely disagrees. Identify:
   - The weakest assumptions I'm making
   - Evidence that could undermine my position
   - Alternative explanations I haven't considered
   - Ways this could fail that I haven't anticipated
   - Who would be harmed by this if it's wrong

3. **Present the strongest counterargument** — What would the most credible critic say?

4. **Rate the robustness of my position** (1-10) — How well does it hold up to scrutiny?

5. **What would change your mind?** — What evidence or argument would make you (as critic) agree with me?

Be genuinely critical. Do not soften your challenge. The goal is to find the weaknesses before they find me.
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## Tips
- This is uncomfortable to use on your favorite ideas — that's exactly when it's most valuable
- Follow up: "Now give me the version of my plan that would hold up against these criticisms"
- Works for business plans, arguments, policies, major life decisions