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Brief an assistant to book 1:1s around a tricky calendar

  • For Managers and team leads
  • You practice Giving the right context
  • Time about 5 minutes

About this exercise

You manage four people and want an AI assistant to book this week's 30-minute 1:1s. Write its brief: each 1:1 must fit that person's latest availability and your free time, it must never move or cancel an existing meeting, and anyone it can't fit goes to you with ASK_HUMAN. It must output exactly 5 numbered plain-text lines: one per person (in the order listed), then a DONE line.

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."
  • Trusting the AI to count words. AI is bad at counting and runs long, especially when it explains each step. Try: Cap each line instead: "each line under 20 words, no explanations."
  • Not naming the hard limits. The AI happily books over a busy block or makes a 1:1 an hour long. Try: Say: "30 minutes each, only inside free time on my calendar and their availability."
  • Missing the latest update. The AI may follow the roster line and miss the Slack message that changes Priya's days. Try: Add: "If a later message changes someone's availability, use the later one."
  • Letting it move meetings. To fit everyone in, the AI may move the exec review without asking. Try: Add: "Never move or cancel a meeting. If someone doesn't fit, ASK_HUMAN."

What a strong prompt includes

  • Sets the length
  • Uses the latest availability
  • Sets what not to touch
  • Makes it ask before anything risky
  • Shows the action-log format

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