{"id":"exec-itinerary-constrained-day","audience":"executive-assistants","category":"leadership-work","track":"leadership","level":"advanced","technique":"constraints","title":"Build a one-day itinerary that respects every hard constraint","free":false,"task":"Plan your executive's Thursday in Chicago as a plain-text itinerary, one line per item with a start time like 08:30, in time order. Respect every fixed time, travel time and buffer in the notes, end with the flight, and add a final line starting \"Flag:\" naming any constraint that cannot be met. Do not invent bookings or times not implied by the notes.","materialLabel":"Notes and constraints (attached to your prompt automatically)","material":"Executive: Imran Siddiqui. Thursday Nov 14, Chicago.\n\nFIXED\n- Breakfast with investor Alma Park at the hotel, 07:30, lasts 45 minutes.\n- Customer meeting at Lakeview Plastics (downtown), 10:00-11:30. Travel from hotel: 25 minutes.\n- Board call (video), 13:00-13:45. Imran must be on video from a quiet room; the hotel business center works.\n- Flight home departs O'Hare at 18:10. Domestic flights: arrive 90 minutes early. Travel downtown to O'Hare: 50 minutes, allow 20 minutes extra for traffic at rush hour (after 15:30).\n- Imran wants 30 minutes of buffer after the customer meeting.\n\nOPTIONAL (only if time)\n- Walkthrough of the new Loop office with Dee Marsh, 45 minutes, anywhere between 14:00 and 16:00. Imran said it is nice to have.\n- Lunch: he must eat; 40 minutes.\n\nEarlier note: the customer meeting was 10:30; it moved to 10:00.","rules":[{"type":"maxWords","max":150},{"type":"plainText"}],"mistakes":[{"title":"Using the old meeting time","why":"The AI plans around 10:30.","fix":"Say: \"The customer meeting moved to 10:00.\"","checks":["r0"]},{"title":"Ignoring the travel math","why":"The AI forgets the drive and the 90-minute airport rule.","fix":"Say: \"Work backward from the 18:10 flight: 90 min early plus travel plus traffic.\"","checks":["r2"]},{"title":"Missing a required item","why":"The AI skips lunch or the buffer.","fix":"Say: \"Include lunch (40 min) and the 30-minute buffer.\"","checks":["r1"]},{"title":"No flag line","why":"The AI hides a conflict.","fix":"Say: \"End with a Flag: line naming any constraint that cannot be met.\"","checks":["r2"]},{"title":"Markdown","why":"The AI makes a bold table.","fix":"Say: \"Plain text, one line per item.\"","checks":["plainText"]},{"title":"Trusting the AI to count words","why":"AI is bad at counting. Ask for a total word limit and it often lands over it.","fix":"Cap each line: \"each line under 14 words.\"","checks":["maxWords"]},{"title":"Trusting the AI to count words","why":"AI is bad at counting. Ask for a total word limit and it often lands over it.","fix":"Cap each part instead, for example: \"each line under 12 words.\"","checks":["maxWords"]}],"promptHints":[{"label":"Time format","patterns":["24-hour","hh:mm","start time"]},{"label":"Work backward","patterns":["backward","working back","leave by"]},{"label":"Hard constraints","patterns":["fixed","hard constraint","must"]},{"label":"Flag line","patterns":["flag:","conflict"]},{"label":"Plain text","patterns":["plain text","one line"]}],"hint":"Ask for time-ordered lines, tell it to work backward from the flight, and ask for a Flag line.","rubricLabels":["Every line starts with a time in 24-hour format, items are in time order, and the customer meeting is at 10:00-11:30 (not 10:30) after leaving the hotel by 09:35","The board call is at 13:00 from the hotel business center, and the plan includes a 40-minute lunch and a 30-minute buffer after the customer meeting","The itinerary ends with leaving for O'Hare by 15:30 or earlier so he arrives 90 minutes before 18:10 allowing for traffic, and the last line starts with \"Flag:\""]}