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Brief an assistant to chase only the right overdue invoices

  • For Freelancers and creators
  • You practice Giving the right context
  • Time about 5 minutes

About this exercise

You're a freelance designer and want an AI assistant to chase late payments. Write its brief: draft (never send) a reminder only for invoices that are past due, unpaid and not disputed, with the subject exactly "Reminder: INV-### was due [date]"; never add late fees; and ask you about anything unclear. Today is Nov 6, and something the tracker doesn't show yet: Harbor & Vine paid INV-104 by bank transfer yesterday. Output a plain-text numbered action log of at most 5 lines, ending with a DONE line that names which invoices got reminders.

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."
  • Leaving out what only you know. The tracker still says INV-104 is unpaid. The AI will nag a client who paid yesterday unless you tell it. Try: Add: "Harbor & Vine paid INV-104 yesterday. Don't remind them."
  • Ignoring the notes column. The AI may nag a client in a dispute or one whose check already arrived. Try: Add: "Skip disputed invoices and any with a note that payment arrived."
  • No subject format. The AI writes chatty subjects like "Friendly follow-up!" that clients skim past. Try: Say: "Subject exactly: Reminder: INV-### was due [date]."

What a strong prompt includes

  • Shares the payment you know about
  • Skips disputes
  • Says draft, never send
  • Sets the subject line
  • Says how to finish

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