Devil's advocate: stress-test any plan or decision
ChatGPT argues against your plan as hard as it can — finds the hidden assumptions, most likely failure modes, and the risks you've normalized — then separates dealbreakers from manageable risks.
Prompt
I'm about to [DECISION OR PLAN — describe it in 2-3 sentences]. I think it's a good idea, but I want you to challenge it before I commit. Play devil's advocate. Try to convince me this is a mistake. Find: - The assumptions I'm making that might be wrong - The things I haven't thought about - The most likely ways this goes badly in 6 months - What I might be telling myself to justify a decision I've already made emotionally Don't soften it. Steelman the case against my plan as if you genuinely believe it's wrong. Then, after the challenge: tell me which of your objections are real dealbreakers vs. things I can manage or mitigate. Tips: • Use this for any irreversible or expensive decision: a job change, a business idea, a major purchase, ending a relationship, moving cities • The best prompt you can add at the end: 'Now tell me — if you were me, what would you actually do?' (sometimes you need both the challenge AND a recommendation) • If the devil's advocate argument doesn't shake you at all, that's actually a good sign. If it does shake you, that's the most valuable 5 minutes you'll spend before deciding
- Source
- promptfork seed
- License
- CC-BY-4.0
- Published
- 6/22/2026