September 15, 2026 · 3 min

Stress-test a plan before you commit

Three minutes. One prompt, one word, one skill. This is the September 15, 2026 issue in full — the prompt, the word, the skill and the mistake.

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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 DayZero-Shot Prompting

Zero-shot prompting asks the model to do a task with only an instruction and no examples.

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

Try ThisTry This

AI can state wrong facts confidently. For names, numbers, dates, and quotes, verify before you rely on them — ask it to cite the source, or check it yourself.

Don't Do ThisDon't let it do arithmetic unsupervised

Language models predict text, so a total can look completely reasonable and still be wrong — and a wrong number in a confident table is harder to spot than a wrong sentence.

Instead: Have it show the working, or better, have it write the formula and run the sum in your spreadsheet. Never paste an AI-generated figure into something financial without recomputing it.

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