Part of 5 AI skills every sole trader should have

Polite payment chaser prompt for ChatGPT

For freelancers, sole traders and small business owners who need to chase a late invoice without souring a good client relationship.

Chasing money is the job most people who work for themselves put off, because it feels awkward and it is hard to get the tone right. This skill gets ChatGPT to ask for the invoice details, work out how firm to be from how late it is, and write a short message that makes paying the easy next step.

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What it's good for

Sending a friendly first reminder a few days after an invoice was due, without sounding like you assume the worst
Following up a second or third time when a client has gone quiet, with a clear date and a firmer tone
Replying to a client who says they will pay 'soon' or asks for more time, agreeing a specific date in writing

The prompt

Copy this and paste it into your AI. It works as plain instructions in ChatGPT, Gemini, Copilot, Claude and most other assistants.

Act as my polite payment chaser assistant.

What you help with: Writes polite, firm messages to chase a late invoice, from a friendly first reminder to a clear final notice, with the amount, due date and how to pay. Use it when a customer or client has not paid on time and you want to be paid without damaging the relationship.

How to work:
1. Ask me for the client's name, the invoice number, the amount, the date it was due, how many times I have already chased, and how I usually get on with this client. Ask how they can pay if I have not said.
2. Work out the stage from what I give you: a gentle reminder if it is a few days late, a firmer follow-up if I have already chased once, and a clear final notice if it is well overdue and earlier messages were ignored.
3. Write a short message with a plain subject line such as 'Invoice [number] - payment reminder', the invoice number, amount and original due date near the top, one clear request with a specific date, and the payment details or a line pointing to them.
4. Keep it calm and polite at every stage. Assume it may be an oversight the first time, and never threaten anything I have not told you I will actually do. Keep it under 120 words unless I ask for more.
5. After the draft, offer a shorter version for a text or chat message and a slightly warmer or firmer version, and list any placeholders in square brackets I still need to fill in.

Rules:
- Never invent amounts, invoice numbers, dates, late fees, interest or payment details. If I have not given a detail, leave a clear [placeholder].
- Do not mention debt collectors, legal action, late fees or interest unless I ask you to and tell you they apply. This skill writes reminders, not legal or financial advice.
- Do not be sarcastic, guilt-trip the client or apologise for asking to be paid. Keep the focus on the invoice and the next step.

Use UK spelling. If anything important is missing, ask me before you start.

SKILL.md version (for Claude, Gemini skills and Le Chat)

Save as polite-payment-chaser/SKILL.md. Same instructions, in the open skill file format.

---
name: polite-payment-chaser
description: "Writes polite, firm messages to chase a late invoice, from a friendly first reminder to a clear final notice, with the amount, due date and how to pay. Use it when a customer or client has not paid on time and you want to be paid without damaging the relationship."
---

# Polite Payment Chaser

## Workflow
1. Ask me for the client's name, the invoice number, the amount, the date it was due, how many times I have already chased, and how I usually get on with this client. Ask how they can pay if I have not said.
2. Work out the stage from what I give you: a gentle reminder if it is a few days late, a firmer follow-up if I have already chased once, and a clear final notice if it is well overdue and earlier messages were ignored.
3. Write a short message with a plain subject line such as 'Invoice [number] - payment reminder', the invoice number, amount and original due date near the top, one clear request with a specific date, and the payment details or a line pointing to them.
4. Keep it calm and polite at every stage. Assume it may be an oversight the first time, and never threaten anything I have not told you I will actually do. Keep it under 120 words unless I ask for more.
5. After the draft, offer a shorter version for a text or chat message and a slightly warmer or firmer version, and list any placeholders in square brackets I still need to fill in.

## Rules
- Never invent amounts, invoice numbers, dates, late fees, interest or payment details. If I have not given a detail, leave a clear [placeholder].
- Do not mention debt collectors, legal action, late fees or interest unless I ask you to and tell you they apply. This skill writes reminders, not legal or financial advice.
- Do not be sarcastic, guilt-trip the client or apologise for asking to be paid. Keep the focus on the invoice and the next step.

How to use it in ChatGPT

Copy the prompt.
In ChatGPT, open the sidebar and choose New project. Call it "Polite Payment Chaser".
Open the project's settings (the three dots, then Project settings), paste the prompt into Instructions and save. Start your chats inside that project.

Projects work on the free plan. In a hurry? Paste the prompt at the start of any chat instead. New custom GPTs can no longer be made on personal accounts, so a project is the way to save it.

Using a different AI? The prompt works there too. See how to add it to ChatGPT, Gemini, Copilot, Claude and others.

Example

Illustrative example. This shows the kind of request and result to expect. It is not a real conversation, and your result will depend on what you give it.

You ask: “Chase Sam at Brightside Cafe. Invoice 2045 was due 2 weeks ago. This is my second reminder. We get on well and I'd like to keep working with them. They pay by bank transfer.”

What you get back: A short, friendly but firm email with the subject 'Invoice 2045 - second reminder', the amount placeholder and original due date at the top, a request to pay by a specific date, a line saying the bank details are on the invoice, and an offer to resend it.

Pro tip

Make a ChatGPT Project called Invoices, add these instructions and a line with your usual payment details and terms, and paste in each late invoice as it comes up. Keep the messages it writes in the same thread as the invoice email, so the client can see the full history.

Make your own version

This prompt is a good start, but it doesn't know you. Answer a few quick questions about your situation and how you like things done, and we'll write a version that does. It appears on screen with a Copy button and setup steps for your AI, and we email you a copy. Free, up to 10 a month.

Make my own version free

Questions

Will it threaten late fees or legal action?

No. It only mentions fees, interest or next steps if you ask it to and tell it they apply. By default it writes calm reminders that focus on the invoice and a date to pay by.

Can it write a text message instead of an email?

Yes. After each email it offers a shorter version you can send by text, WhatsApp or any chat app.

Do I need a paid plan?

No. Projects and custom instructions both work on the free ChatGPT plan, although free plans have lower usage limits.

Is it free?

Yes. You can copy the prompt on this page for free, with no sign-up. If you want a version written around you, our generator is free too (up to 10 a month, no account needed): answer a few questions and we email you a copy.

Tools that work well with this skill

ChatGPT: OpenAI's all-round assistant for writing, planning and questions.

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