{"id":"wri-mgr-decline-pto-request","audience":"managers","category":"writing-emails","technique":"tone","title":"Turn down a time-off request and offer dates that work","free":false,"task":"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.","materialLabel":"Jordan's request and your team calendar (attached to your prompt automatically)","material":"SLACK DM from Jordan Ellis, Mon 9:12 am:\nHey! Can I take Dec 22 - Jan 2 off? My family is doing a big trip this year and I already looked at flights. I know it's close season, totally understand if it's tricky. Let me know when you can!\n\nTEAM TIME-OFF CALENDAR (Accounts Payable, 5 people)\n- Priya: Dec 22-26 (approved)\n- Luis: Dec 22 - Jan 2 (approved)\n- Chen: Dec 29-31 (approved) -> WITHDRAWN Nov 3, Chen is working those days now\n- Dana: no time off\n- Jordan: requesting Dec 22 - Jan 2\n\nPOLICY: During year-end close (Dec 15 - Jan 10), no more than 2 of the 5 AP team members can be out on the same day.\n\nMy math:\n- Dec 22-26: Priya + Luis already out = 2. Adding Jordan makes 3. Can't approve.\n- Dec 29 - Jan 2: only Luis out (Chen withdrew). Adding Jordan makes 2. I can approve that.\n\nNotes:\n- Jordan is great, one of my best people.\n- Priya booked first, back in September.\n- Schedule gets locked Friday.","rules":[{"type":"maxSentences","max":4},{"type":"plainText"}],"mistakes":[{"title":"Not limiting the length","why":"AI writes a long, softened message with several paragraphs of cushioning.","fix":"Be exact: \"At most 4 sentences, Slack DM.\"","checks":["maxSentences"]},{"title":"Burying the no","why":"AI opens with \"Thanks for asking!\" and \"I totally understand\", so the answer shows up halfway down.","fix":"Add: \"Sentence 1 says Dec 22-26 can't be approved.\"","checks":["r0"]},{"title":"No alternative or deadline","why":"The AI says no and stops, or forgets you need an answer by Friday.","fix":"Add: \"Offer Dec 29 - Jan 2 and ask Jordan to confirm by Friday.\"","checks":["r1"]},{"title":"Over-sharing who's out","why":"The AI explains the calendar by naming Priya and Luis, which is their business.","fix":"Add: \"Don't name anyone who is out. Just cite the 2-person limit.\"","checks":["r2"]},{"title":"Forgetting where it gets pasted","why":"AI adds bold and headings by default, which show up as ** and # clutter in Slack.","fix":"Add: \"Plain text, no bold, no headings.\"","checks":["plainText"]}],"promptHints":[{"label":"Limits the sentences","patterns":["\\b(\\d|one|two|three|four|five|six)\\b.{0,12}sentences?","sentences?"]},{"label":"Gives the answer first","patterns":["first sentence","lead with","start with","answer first"]},{"label":"Offers the dates that work","patterns":["dec(ember)?\\s*29","jan(uary)?\\s*2"]},{"label":"Protects privacy","patterns":["don'?t name","no names","privacy","without naming"]},{"label":"Asks for plain text","patterns":["plain","no bold","no markdown","no formatting","no headings"]}],"hint":"Saying no kindly still means saying it first. Tell the AI the order, the alternative, the reason, and what not to reveal.","rubricLabels":["The first sentence (a short greeting like 'Hi Jordan,' before it is fine) clearly says Dec 22-26 can't be approved, with no thank-you or small talk before it","Offers Dec 29 - Jan 2 as dates that can be approved, gives the reason (no more than 2 of the team out at once during year-end close), and asks Jordan to confirm by Friday","Does not name any teammate who is out (Priya, Luis or Chen) and does not suggest swapping with anyone"]}