Late payment in a small services business is rarely a dispute. It is a customer who meant to pay you, an accounts inbox that files anything without a reference number, and nobody on your side whose job it is to notice.
Chasing is unpleasant, so it happens late, and it happens in an inconsistent tone: three polite weeks of nothing, then one message you regret. An automation fixes the timing and the tone at the same time, because the words were written on a calm afternoon rather than at the moment you looked at the bank balance.
Budget an afternoon for this build. It runs against whatever you already raise invoices in.
What you are building
A ladder of five reminders that starts before the invoice is due and ends at a clear decision point, plus a Friday summary of who owes what so you never have to go looking. The reminders are drafted once by an AI assistant in your wording, and sent by an automation tool that checks the payment status first.
Tools: your invoicing or accounting software, a spreadsheet, an automation tool (Zapier, Make or n8n), an AI assistant (ChatGPT or Claude) and the email account you already invoice from.
Step 1: fix the invoice before you automate the chasing
Half of late payment is caused by the invoice itself. Open the last five you sent and check each one has a due date written as an actual date rather than a payment term, the exact reference the customer asked for, one payment method with the details on the document, and a named person in the To field rather than an accounts alias on its own.
Fixing those four things removes the most common honest reason an invoice sits unpaid, which is that somebody could not work out how or when to pay it. Automating a chase for an invoice nobody can process only annoys people faster.
Step 2: build the ladder
Five touches, each with a different job and a different temperature. Write the dates relative to the due date so the ladder works for every payment term you use.
- Three days before due. A neutral heads-up with the amount, the due date and the payment details repeated. No question in it, nothing to answer.
- On the due date. A short note that it falls due today with the invoice attached again. Attaching it again matters, because the original is buried by now.
- Seven days late. Ask a question instead of repeating the amount: has this been scheduled for payment, and if not, what does it need from us. Questions get answered, statements do not.
- Fourteen days late. Move the conversation to the person who signed the work off and copy accounts. Keep it factual: invoice number, date of the work, amount.
- Thirty days late. State what happens next, whether that is work paused, statutory interest applied or the account passed on. Say it plainly, once, then do the thing you said.
Do not put a threat in touch one and do not still be apologising at touch five. The entire value of writing this ladder in advance is that the escalation is decided by a schedule instead of by your mood.
Step 3: write the five emails once
Give the AI assistant the ladder, your tone, and the constraint that matters most here: these are emails to people you want to keep working with.
Write five payment reminder emails for my business, one for each of these stages: three days before due, on the due date, seven days late, fourteen days late, thirty days late. Business: [one line]. My tone with customers is [three adjectives]. Use the placeholders CLIENT_NAME, INVOICE_NUMBER, AMOUNT, DUE_DATE, WORK_DESCRIPTION and PAYMENT_DETAILS. Each email under a hundred and twenty words, with a subject line. Escalate the firmness gradually and evenly. Never sarcastic, never apologetic for asking, no exclamation marks. In the last one, state consequences as facts rather than threats.
Read them as though you were the customer receiving them. The test for each is simple: would you be comfortable if this email was forwarded to the person who hired you. If not, rewrite that step now, while it is one email rather than a habit.
Step 4: wire it up
The mechanics are the same shape as any scheduled automation. The important part is the check immediately before the send.
- Once a day, pull the list of unpaid invoices from your accounting software. Most packages have a connector; if yours does not, a scheduled export into a Google Sheet works and takes a minute to set up.
- Work out the difference between today and each due date, and match it against the five stages.
- For any invoice that matches a stage, re-check the paid status directly, then fill in the template for that stage.
- Send from the address you invoice from, with the invoice attached, and log the send in a sheet with invoice number, stage and timestamp.
- Route stages four and five to your own inbox as drafts rather than sending them. The last two are conversations, and they deserve thirty seconds of your attention.
One safety valve is worth building in: a stop column in the sheet. When a customer agrees a payment plan, or you decide to give somebody room, tick it, and have every stage check that column before it sends anything.
Step 5: the Friday number
The second half changes how the business feels rather than how the inbox behaves. Have the same automation send you one message every Friday morning with three things: total outstanding, the oldest unpaid invoice and its age, and anything that reached stage four this week.
Here is a list of my unpaid invoices with customer, amount, invoice date and due date. Write a short internal summary for me, the owner. Give me: total outstanding, the count of invoices past their due date, the three oldest with customer name and how many days late, and one line naming anything that needs a phone call rather than another email. Use the figures exactly as given and do not calculate anything I have not provided. Plain sentences, no preamble, no advice about cash flow, under a hundred and twenty words.
That summary takes ten seconds to read and it replaces the vague background sense that some money is out there somewhere. It is also the part you will still be using long after the novelty of the reminder emails has worn off.
What changes
What changes is not that customers suddenly pay on the day. What changes is that every invoice gets the same five touches in the same order, whether or not you had a good week, and you stop being the bottleneck in your own accounts.
The chasing sequence is a Workflow 05: Build Automation Workflows build, and the Friday number belongs to Workflow 07: Run a Leaner Business, the AutomateFirst module about the weekly rhythm that keeps everything else running. Both are in the playbook with the prompts and a checklist, seven workflows for one payment of $297.
Workflow 05: Build Automation Workflows, and Workflow 07: Run a Leaner Business
Six more workflows, written exactly like this one
The AutomateFirst playbook covers seven repetitive jobs end to end, with the prompt library, PDF checklists and lifetime access. One payment of $297, no subscription.
Other guides