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 ThisTry This

Use AI to think, not just to type. 'Poke holes in this,' 'what am I missing,' 'argue the other side' — it's a free thought partner, which is often worth more than the draft.

Don't Do ThisDon't paste a citation you haven't opened

A model will produce a case name, a study, or a page number in exactly the right shape and with total confidence, and the source may not exist. The formatting is not evidence.

Instead: Open every link and search for the exact quoted sentence before it leaves your desk. If you cannot find the source in thirty seconds, cut the claim.