ChatGPT prompt for chasing an overdue invoice

This is the prompt we run the moment an invoice passes a week overdue: it drafts the whole escalation ladder at once, from the friendly assumption of an oversight to the final notice before collections. Its rule: it states the consequences set in the contract plainly, but never invents a penalty you did not give it.

The prompt to copy

Invoice {number} for {amount} to {client} is {N} days overdue; relationship context: {one line}. Draft escalating messages for day 7, day 21, and day 40: friendly assumption of oversight → firm with consequences stated plainly → final notice before {next step}. Professional throughout.

Replace the fields in curly braces (number, amount, client, days overdue, relationship context, and next step), then run: you get all three messages in one pass.

When to use it

The moment an invoice passes 7 days overdue. Rather than writing one reminder, waiting, then rewriting a firmer one two weeks later in a worse mood, you prepare the whole sequence now. All that is left is sending the right message on the day.

What you get back

1. A day 7 message, friendly, assuming a simple oversight.
2. A day 21 message, firm, with the consequences stated plainly.
3. A day 40 final notice, before the next step you named.
4. A professional tone throughout, ready to copy.

Real example: late invoice → ready chase sequence

Input: at Brightside Studio, an 8-person brand agency, founder Maya chases client Fernhill Coffee. The fields she filled in:

Invoice 2026-041 for £2,400 to Fernhill Coffee, 24 days overdue.
Relationship context: loyal client for two years, usually prompt, gone quiet since we sent it.
Next step: handing it to our collections agency.

Output, the firm day 21 message, as generated:

Subject: Invoice 2026-041 awaiting payment

Hello,

I am following up on invoice 2026-041 (£2,400), now more than three weeks overdue and still unanswered after our first note.

Please arrange payment within eight days. Otherwise the late-payment penalties set out in clause [clause reference] of our agreement will apply, and we will have to pause the work in progress.

I am happy to help if some difficulty is behind this delay.

Best regards, Maya

Notice what the AI did not do: it invented no penalty rate. Maya did not give it one, so the output points to the contract clause, marked [clause reference], rather than quoting a percentage at random. Replacing the marker takes ten seconds; sending a false figure in a chase exposes you far more.

This prompt is part of the library that ships inside the kit, with its usage note.