Ask ‘what would make this answer wrong?’
Works with ChatGPT · Claude · Gemini
Stress-test an answer by asking how it could be wrong.
The problem
A single confident answer hides the conditions under which it fails.
What this skill does
Asking how it could be wrong surfaces hidden assumptions and edge cases.
When to use it
- Use before relying on an important answer.
Juni’s tip
Juni says: the fastest way to trust an answer is to try to break it.
The prompt
Try it live
Fill in the blanks — your ready-to-use prompt builds as you type.
Weak vs. better
is this correct
Take this answer — [answer] — and stress-test it: list the assumptions it depends on, the conditions under which it would be wrong, and the edge cases it doesn't handle. Then give a more cautious version.
Why this works
Asking how an answer fails reveals the assumptions you'd otherwise discover the hard way.
Practice task
Take an answer you're about to act on and ask what would make it wrong.
Self-check
- Hidden assumptions are surfaced
- Failure conditions and edge cases are named
- A more cautious version is offered
Common mistakes to avoid
- Accepting the first confident answer
- Not naming the assumptions it rests on
- Ignoring edge cases entirely
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