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Pick a flight for your exec against travel constraints

  • For Executive assistants
  • You practice Setting limits and rules
  • Time about 5 minutes
  • Level Advanced

About this exercise

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.

Common mistakes when you ask AI for this

  • Not stating her rules. The AI picks the cheapest fare, which is a red-eye. Try: List her rules: "No red-eyes, land by 8 pm, economy plus only, Atlas if within $100."
  • Comparing against the wrong fare. The AI measures Atlas against the cheapest fare overall, $410, which is ruled out. Try: Add: "Compare Atlas to the cheapest option that passes every rule."
  • No visible math. The AI says "slightly more expensive" without numbers you can check. Try: Add: "Show the fare difference as math, like $640 - $575 = $65."
  • Verdict first or buried. The AI leads with its pick, before checking the options. Try: Say: "One line per option, then the last line: Recommendation:"
  • Long markdown answer. The AI writes a formatted comparison with headings and bold. Try: Say: "Plain text, one short line per option, under 100 words."

What a strong prompt includes

  • States the travel rules
  • Gives the airline preference rule
  • Asks to show the math
  • One line per option
  • Ends with a recommendation

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