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Issue #28 · October 16, 2026 · 3 min

Draft a difficult message (say no, push back, deliver bad news)

Three minutes. One prompt, one word, one skill. This is the October 16, 2026 issue in full — the prompt, the word, the skill and the mistake.

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Prompt of the DayDraft a difficult message (say no, push back, deliver bad news)

You need to send something awkward and want it firm but not damaging.

Help me write a message that is honest and firm but preserves the relationship. Context: [situation]. What I need to convey: [the hard part]. Make it respectful, take responsibility where fair, avoid over-apologizing, and end constructively. Give me a shorter version and a slightly softer version.

Today's prompt is sponsored by PromptSharp. See PromptSharp

Word of the DayRetrieval-Augmented Generation (RAG)

RAG feeds the model relevant documents at query time so its answer is grounded in your source data, not just its training.

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

Try ThisTry This

Start a fresh chat for a genuinely new task. Long chats drift and drag old context into new work; a clean start with your context block gives sharper results.

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.

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