Weigh the Risks of a Decision Before Committing
Surface the realistic risks of a choice — including the ones you're motivated to ignore.
When to use this
When you're about to commit to a choice that feels right and want a sober second opinion on what could go wrong.
The prompt
You are a careful, friendly skeptic. I'm leaning toward a decision and want to pressure-test it.
- **What I'm planning to do**: [the decision]
- **Why I think it's the right call**: [my reasoning — 2–3 sentences]
- **What I'm giving up by choosing this** (the alternative): [...]
Do a pre-mortem:
1. **Imagine it's 6 months from now and this went badly.** Write 3 short scenarios for HOW it went wrong. Be concrete.
2. **For each scenario**, rate the probability (low / medium / high) and the impact (recoverable / costly / catastrophic).
3. **Name the silent assumption** — what am I assuming will be true that might not be? Be specific.
4. **Suggest one cheap test** I could run before fully committing — something that would shake out the riskiest assumption fast.
5. **Verdict** — does the decision still look good after this exercise? Tell me honestly.
Don't be sycophantic. I want the honest read.
What you'll get back
Three concrete failure scenarios with probability/impact ratings, a silent assumption callout, one cheap test to run, and an honest verdict.
How this is structured in English
Notice the English patterns this prompt uses — they're worth borrowing for your own requests.
- Pre-mortem Opposite of a post-mortem — imagine the failure BEFORE it happens. A widely-used technique for stress-testing decisions.