Brief an assistant to approve time off only when it's safe

About this exercise

You want an AI assistant to handle PTO requests for the 4-person support team. Write its brief: it may approve a request only if it is 5 days or fewer, falls outside the Dec 21-Jan 2 blackout, and leaves at least 2 of the 4 people working every day; anything else goes to you with ASK_HUMAN saying which rule it breaks; and it never denies a request itself. Output exactly 5 numbered plain-text lines: one per request in order, then DONE.

Common mistakes when you ask AI for this

• Not showing the log format. Left alone, the AI writes a friendly report with headings instead of a checkable action log. Try: Show it literally: "Format every line like 1. ACTION: tool(args), then ASK_HUMAN: and DONE: lines. Plain text."
• Not giving the rules. The AI approves anything with a good reason, including a 6-day trip. Try: Add: "Approve only if 5 days or fewer, outside Dec 21-Jan 2, and 2+ people still working each day."
• Not asking for the reason. The AI flags requests without saying why, so you redo the check. Try: Add: "For anything else, ASK_HUMAN naming the rule it breaks."
• Letting it say no. Given deny, the AI rejects requests on its own, which should be your call. Try: Add: "Never deny. End with DONE."

What a strong prompt includes

• Caps the length
• Names the blackout
• Sets coverage
• Forbids denying
• Shows the action-log format

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