Why this matters
Late invoices are cash you already earned. Most small firms know it, and still the chasing happens in bursts, when someone has a free hour and an aging report open. Who do you write to first? How firm should each note be? The oldest, biggest invoice should not wait behind a friendly nudge.
One mistake costs more than the delay: sending a payment reminder to a customer who has a dispute open. It makes you look like you are not listening, and it can hurt a client you want to keep.
In this module you give ChatGPT an accounts receivable aging report and get a ranked chase list for the week, the right tone for each reminder, three ready-to-send emails, and a note on how to handle the one disputed invoice before any reminder goes out.
What you’ll build
A chase list for Harbor Lane Studio, a made-up design studio, as of October 13, 2026. Twelve open invoices: two not due yet, nine past due to chase, and one disputed (Pioneer Valley Credit Union, held back).
The list is sorted oldest bucket first, largest amount first inside each bucket, with a friendly, firm or final-notice tone and totals for each bucket. Then three short emails (final notice to Ridgeline Accounting, firm to Fairview Orthodontics, friendly to Hollis Architects) and a two-line plan for the dispute.
What you need
- Nothing to start the practiceChatGPT is a practice copy and the aging report is already in the file picker.
- A ChatGPT account that can read files, to do it for realUse a business plan, and follow your firm’s policy on customer data.
- An aging report as a CSVExport it from your accounting software. It needs customer, invoice number, invoice date, due date, amount, days past due, contact name and a notes column for promises and disputes.
- Notes on promises and disputesPut them in the notes column. ChatGPT only knows what is in the file.
Concepts
3 ideas you’ll use in the practice.
Say how to sort and what to leave out
Tell ChatGPT to leave out invoices that are not past due, put disputed invoices in a separate list, and sort oldest bucket first, largest amount first inside each bucket.
Ask for totals per bucket so you can see how much is old money.
Match the tone to the age
Friendly for one to thirty days, firm for thirty-one to ninety, and a final notice after ninety. Say that in the request and each email starts at the right temperature.
Use only what is in the file: contact name, invoice number, amount and due date. Tell it not to mention late fees or legal action unless you decide to.
Hold back disputes
A disputed invoice gets no reminder until the dispute is settled. Ask ChatGPT for a short note on how to handle it instead.
You still read every email before it goes out. ChatGPT does not know what you promised on the phone last week.
Practice
Do every step yourself in a practice copy of the real tool. It checks your work, and “Do it for me” finishes any step you get stuck on.
Do it for real
Now repeat it in your own account. Tick each step as you go.
Downloads
- Sample AR aging report, October 2026 (.csv)The 12-invoice file from the lesson, made-up data with one dispute and one broken promise to pay.
Quick check
3 questions to check you’ve got it.
1. An invoice is marked Disputed. What do you do?
- Send a firm reminder
- Keep it off the chase list and settle the dispute first
- Mark it paid
Show the answer
Keep it off the chase list and settle the dispute first. A reminder during a dispute looks like you are not listening.
2. How should the chase list be sorted?
- Alphabetical by customer
- Oldest bucket first, largest amount first inside each bucket
- Newest invoice first
Show the answer
Oldest bucket first, largest amount first inside each bucket. The oldest, biggest invoices are the cash you are most at risk of losing.
3. Which details should the emails use?
- Only what is in the file
- Whatever ChatGPT thinks is likely
- Late fees and legal action
Show the answer
Only what is in the file. Tell it not to guess, and not to mention fees or legal action unless you chose to.