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Brief an assistant to run a contractor's onboarding checklist

  • For HR and recruiting
  • You practice Giving the right context
  • Time about 5 minutes

About this exercise

You want an AI assistant to work through the onboarding checklist for a new hire. Write its brief: use the latest start date, skip benefits and payroll because she is a contractor (paid through the vendor portal), send any purchase over $1,500 to you with ASK_HUMAN, and draft (never send) the welcome email. Output a plain-text numbered action log of at most 6 lines, under 150 words, ending with 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."
  • Missing the latest update. The AI copies the start date from the record and misses the manager's later email. Try: Add: "If a later email changes a detail, use the newer one."
  • Not saying what's different about her. The AI runs the standard checklist top to bottom, including benefits and payroll she shouldn't get. Try: Add: "She's a contractor paid through the vendor portal. Skip benefits and payroll."
  • No spending or sending limit. The AI orders the laptop designers usually get and sends the welcome email itself. Try: Add: "Purchases over $1,500 go to ASK_HUMAN. Draft emails, never send."

What a strong prompt includes

  • Mentions the contractor status
  • Sets a spending limit
  • Uses the latest date
  • Says draft, never send
  • Shows the action-log format

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