Stress-test a plan before you commit

Prompt of the DayStress-test a plan before you commit

You have a plan or proposal and want to find the holes first.

Act as a sharp, skeptical advisor who wants me to succeed. Here is my plan. Do four things: (1) name the 5 biggest risks or weak assumptions; (2) for each, the question a critic will ask; (3) what would have to be true for this to work; (4) the single change that would most improve the odds. Be direct, not polite.

My plan:
[paste plan]

Today's prompt is sponsored by PromptSharp. See PromptSharp

Word of the DayOutput Formatting

Output formatting is instructing the model to return a specific structure — a table, JSON, bullets — so results are usable and consistent.

Every Word of the Day becomes a permanent page. Full definition →

Try ThisRehearse a hard conversation with AI first

Say: 'Play [my manager / this client]. I'll practice asking for [X]. Push back realistically, then tell me how I did and what to say instead.'

1. Set the scene and who AI is playing.
2. Run the conversation for real.
3. Ask for feedback + better lines.

Don't Do ThisDon't fight a refusal — reframe the ask

Arguing with a model that declined a request burns time and usually fails, because the refusal is about how the request was phrased, not about you.

Instead: State the legitimate purpose and the audience plainly: "I'm the account owner writing a policy summary for our internal team." Genuine context usually resolves it in one turn.