Emails, Money and GST

Chase an unpaid invoice without the awkwardness

A firm but friendly reminder email for an overdue invoice, in a softer and firmer version, ready to send.

Why it helps

Nobody likes chasing money. So the email sits in your head for a week while the invoice gets older. Tell AI the facts and how you want to come across, and it gives you wording that's clear about what's owed without sounding grovelling or rude.

The same approach works for the other emails you keep putting off: turning down a job, saying no to a discount request, or pushing back on scope creep. Say what happened and the tone you want, and let AI take the heat out.

The prompt

Copy it, swap the bits in [square brackets], and paste it into ChatGPT, Claude, Gemini or Copilot.

Copy and paste

Help me write a polite but firm email to a customer whose invoice is overdue. I'm a [type of business] in New Zealand. - Invoice number: [number]. Amount: [amount, incl GST]. Due date was [date]. This is my [first / second / final] reminder. - Tone: friendly and professional, not grovelling, not aggressive. NZ English. - Keep it under [120] words. - Include a placeholder for payment details: [bank account and reference]. - Ask them to pay within [7] days, or to get in touch if there's a problem so we can talk about it. - Use the amounts and dates exactly as I've given them. Don't add late fees, interest or legal threats unless I tell you to. Anything else to know: [e.g. they're usually good payers, or they've stopped replying] Give me a softer version and a firmer version.

Then keep chatting

  • Write a 2-line text message version for a quick nudge.

  • Write a third reminder that says this is my final reminder before I consider next steps, without threatening anything specific.

  • They've replied saying money is tight. Help me offer a simple payment plan of [amount] a week.

  • Help me politely turn down a job I don't want, without burning the bridge.

  • A customer wants a discount after the job's done. Help me say no kindly.

Step by step

  1. Check your accounting app (Xero, MYOB, QuickBooks) first. Make sure the invoice really is unpaid and was sent to the right email.
  2. Fill in the prompt with the invoice number, amount, due date and which reminder this is.
  3. Pick the softer or firmer version, depending on the customer and how late it is.
  4. Check the amount, invoice number, due date and payment details against the invoice itself.
  5. Send it from your usual email, with the invoice attached again. Pop a reminder in your calendar for the new due date.

Worked example

What you paste in
I'm a self-employed electrician. Invoice number: 1042. Amount: $1,380 incl GST (example figure). Due date was 20 September. This is my second reminder. They're usually fine, just slow, and the first reminder got no reply.
What you get back
Softer version: Subject: Invoice 1042, friendly reminder Hi [name], Just following up on invoice 1042 for $1,380 incl GST, which was due on 20 September. I know these things slip through the cracks, so I've attached it again. Payment details: [bank account and reference] Could you pop it through in the next 7 days? If there's a problem with the invoice, just let me know and we'll sort it out. Thanks, [your name] Firmer version: Subject: Invoice 1042 now overdue Hi [name], This is my second reminder about invoice 1042 for $1,380 incl GST, due on 20 September. I haven't heard back yet, so I've attached it again. Please arrange payment within 7 days to [bank account and reference]. If something's holding it up, please reply or call me on [phone] so we can work it out. Regards, [your name]

Example details are made up. Your results will vary, so always read and check before you use them.

Watch out for

  • Privacy: don't paste the whole email chain with names, addresses and phone numbers. Summarise what happened in a sentence or two.
  • Check every number against the actual invoice, and only mention late fees or interest if they're in your terms of trade and the customer agreed to them.
  • Don't let the AI threaten legal action or debt collection. If it's got to that point, look at disputestribunal.govt.nz for smaller claims, or talk to a lawyer or a reputable debt collector before you send anything.
  • If you're GST registered, your invoice needs to meet IRD's rules for taxable supply information. Check ird.govt.nz if you're unsure.

Go further

Save the softer, firmer and final versions as email templates, so next time you only change the number and date. Most accounting apps can send automatic payment reminders too. Paste the AI's wording into those reminder templates, and you may never need to write a chaser by hand again.

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