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]

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Word of the DayToken

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Try ThisTurn a fuzzy goal into a week-by-week plan

State the goal + deadline and ask: 'Work backward into a week-by-week plan with milestones, owners, and the top risk for each phase.'

1. Give goal, deadline, and constraints.
2. Ask for a backward-planned timeline.
3. Assign real owners and adjust dates.

Don't Do ThisDon't ask the model "is this correct?"

Models are agreeable by default. Ask "is this right?" and you will almost always be told yes — including about the parts that are wrong.

Instead: Ask it to attack the work instead: "What are the two weakest assumptions here, and what evidence would disprove them?" You get a critic rather than a cheerleader.