Turn down a time-off request and offer dates that work

About this exercise

Jordan asked for Dec 22 to Jan 2 off, and you can't approve all of it. Reply in a Slack DM of at most 4 sentences, plain text. The first sentence gives the answer, then offer the dates you can approve and the policy reason. Don't name the teammates who are out, since that's their private business. Write a prompt that gets that reply.

Common mistakes when you ask AI for this

• Not limiting the length. AI writes a long, softened message with several paragraphs of cushioning. Try: Be exact: "At most 4 sentences, Slack DM."
• Burying the no. AI opens with "Thanks for asking!" and "I totally understand", so the answer shows up halfway down. Try: Add: "Sentence 1 says Dec 22-26 can't be approved."
• No alternative or deadline. The AI says no and stops, or forgets you need an answer by Friday. Try: Add: "Offer Dec 29 - Jan 2 and ask Jordan to confirm by Friday."
• Over-sharing who's out. The AI explains the calendar by naming Priya and Luis, which is their business. Try: Add: "Don't name anyone who is out. Just cite the 2-person limit."
• Forgetting where it gets pasted. AI adds bold and headings by default, which show up as ** and # clutter in Slack. Try: Add: "Plain text, no bold, no headings."

What a strong prompt includes

• Limits the sentences
• Gives the answer first
• Offers the dates that work
• Protects privacy
• Asks for plain text

Practice this now ↑

Related exercises

• Accept a job offer and confirm the exact terms (Writing AI · Job seekers)
• Announce a hybrid work policy change with clear actions (Writing AI · HR and recruiting)
• Announce a promotion with the right date and no pay details (Writing AI · HR and recruiting)
• Announce a team change and answer the first question (Writing AI · Managers and team leads)
• Announce a team meeting change people will actually follow (Writing AI · Managers and team leads)