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

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Try ThisTry This

Treat it as a conversation, not a vending machine. The magic is in the second, third, and fourth message — 'more specific,' 'shorter,' 'now for executives' — not the first.

Don't Do ThisDon't retype your context every morning

Pasting the same background about your team, product and constraints into every new chat is the single biggest hidden time cost of using AI at work.

Instead: Write the context block once, save it somewhere you can reach in two keystrokes, and paste it at the top. Most tools now have a memory or custom-instructions setting that does it for you.