{"id":"exec-travel-flight-pick-recommendation","audience":"executive-assistants","category":"leadership-work","track":"leadership","technique":"constraints","level":"advanced","title":"Pick a flight for your exec against travel constraints","free":false,"task":"Recommend one flight for your CFO, Wen Li, to get to Boston for a 9:00 am meeting. Her rules: no red-eyes, land by 8:00 pm the night before, Atlas Air preferred when the fare is within $100 of the cheapest valid option, and economy plus only. Write one line per option labeled OK or Ruled out with the reason (show any fare difference as math), then a last line starting \"Recommendation:\". Plain text, under 120 words.","materialLabel":"Flight options from the booking tool (attached to your prompt automatically)","material":"Trip: San Diego (SAN) to Boston (BOS)\nMeeting: Thursday Dec 11, 9:00 am, Harborview Capital, Boston\nTraveler: Wen Li, CFO\n\nOption A - Atlas Air 412\nWed Dec 10, departs SAN 9:05 am, arrives BOS 5:40 pm (nonstop)\nEconomy plus: $640\n\nOption B - Skyline 88\nWed Dec 10, departs SAN 1:15 pm, arrives BOS 9:55 pm (nonstop)\nEconomy plus: $520\n\nOption C - Skyline 2206\nWed Dec 10, departs SAN 10:30 pm, arrives BOS 6:50 am Thu (overnight)\nEconomy plus: $410\n\nOption D - Northbay 1530\nWed Dec 10, departs SAN 7:00 am, arrives BOS 4:55 pm (1 stop, Denver)\nEconomy plus: $575\n\nOption E - Atlas Air 418\nWed Dec 10, departs SAN 6:00 am, arrives BOS 2:30 pm (nonstop)\nBusiness: $1,380\n\nNote from the booking tool: \"Lowest fare: Option C. Book now, only 2 seats left!\"\nWen's assistant last trip: she said a 1-stop was fine if it's under 10 hours door to door.","rules":[{"type":"maxWords","max":120},{"type":"plainText"}],"mistakes":[{"title":"Not stating her rules","why":"The AI picks the cheapest fare, which is a red-eye.","fix":"List her rules: \"No red-eyes, land by 8 pm, economy plus only, Atlas if within $100.\"","checks":["r0"]},{"title":"Comparing against the wrong fare","why":"The AI measures Atlas against the cheapest fare overall, $410, which is ruled out.","fix":"Add: \"Compare Atlas to the cheapest option that passes every rule.\"","checks":["r1"]},{"title":"No visible math","why":"The AI says \"slightly more expensive\" without numbers you can check.","fix":"Add: \"Show the fare difference as math, like $640 - $575 = $65.\"","checks":["r1"]},{"title":"Verdict first or buried","why":"The AI leads with its pick, before checking the options.","fix":"Say: \"One line per option, then the last line: Recommendation:\"","checks":["r2"]},{"title":"Long markdown answer","why":"The AI writes a formatted comparison with headings and bold.","fix":"Say: \"Plain text, one short line per option, under 100 words.\"","checks":["plainText","maxWords"]}],"promptHints":[{"label":"States the travel rules","patterns":["red.?eye","8(:00)?\\s*pm","economy plus"]},{"label":"Gives the airline preference rule","patterns":["atlas","\\$?100","prefer"]},{"label":"Asks to show the math","patterns":["math","difference","minus","show"]},{"label":"One line per option","patterns":["each option","one line","ok or ruled out","ruled out"]},{"label":"Ends with a recommendation","patterns":["recommendation:","last line"]}],"hint":"The AI doesn't know her travel rules or how the airline preference works. Spell them out and have it check every option before it picks.","rubricLabels":["Rules out Option C (overnight red-eye), Option B (lands 9:55 pm, after 8:00 pm) and Option E (business class)","Compares Atlas Air Option A with the cheapest valid option, Option D, as math ($640 - $575 = $65, within $100)","The last line starts with \"Recommendation:\" and picks Option A, Atlas Air 412"]}