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Reply to a time-off request that hits a blackout week
Practice: Getting the tone right. About 5 minutes.
About this exercise
Your team member Jess asked for time off during the year-end blackout period. Reply in under 90 words, plain text, with the answer in the first sentence, the reason in one sentence, and the two alternatives your notes allow. Be warm but not apologetic more than once, and don't promise anything HR hasn't approved.
Common mistakes when you ask AI for this
- Burying the answer. The AI opens with congratulations and empathy, so Jess has to read to the end to find the no. Try: Add: "First sentence: I can't approve the full week."
- Trusting the AI to count words. AI is bad at counting. Ask for a total word limit and it often lands over it. Try: Cap each part instead: "4 sentences, each under 18 words."
- Saying no with no path. The AI declines and stops, or offers vague 'let's figure something out'. Try: Add: "Offer both options: Dec 29 off with Ravi covering, or Jan 12-16."
- Promising too much or over-apologizing. To be kind, the AI hints at exceptions or apologizes three times. Try: Add: "No exceptions, extra days or comp time. One apology at most."
- Formatting a Slack reply. The AI adds bold and bullet points that look like a form letter. Try: Add: "Plain text, short, like a normal Slack message."
What a strong prompt includes
- Puts the answer first
- Offers the alternatives
- Limits promises
- Sets the tone
- Sets a word limit
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