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Chase a late payment politely but firmly

Practice: Getting the tone right. About 5 minutes.

About this exercise

Your client Greg is 3 weeks late on part of an invoice. Write a friendly but firm reminder email of at most 4 sentences, plain text. Open with the exact amount still owed, counting every payment in your notes, and the invoice number (no "hope you're well" first). Ask him to confirm a payment date by Friday, don't apologize, and don't mention the late fee, since you're waiving it this time. Write a prompt that gets you exactly that.

Common mistakes when you ask AI for this

  • Missing a payment. The AI trusts the payments list or the $1,800 total and misses the newer $300 in your notes, which annoys a client who already paid. Try: Add: "He paid $600 and then $300, so ask for the $900 balance."
  • Warming up before the point. AI opens every email with "I hope this email finds you well," which softens the one thing Greg needs to see. Try: Add: "First sentence after 'Hi Greg,' states the balance and invoice number."
  • Sounding sorry or threatening. The AI either apologizes for asking or quotes the late fee from the contract. You want neither. Try: Add: "Friendly but firm. No apology. Don't mention the late fee."
  • No length limit. AI writes reminder emails with a warm-up paragraph, a recap of the work and a long sign-off. Try: Add: "At most 4 sentences."
  • Forgetting it's an email. AI may add a bold subject line or bullet points that look like a form letter. Try: Add: "Plain text, short paragraphs, no bold."

What a strong prompt includes

  • Uses the right amount
  • Puts the amount first
  • Sets the tone
  • Leaves out the late fee
  • Sets a length limit

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