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Bruno Ashford @brunoashfordSubscribeModule 9 · Lesson 9.4 · 10 min
Invoices and Collections
Prepare consistent invoices, polite collection reminders and an aging list, so late payments get chased on time without damaging relationships.
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1Keep one source of truth for open invoices
Export open invoices from your accounting or invoicing tool as CSV: client, invoice number, amount, issue date, due date, contact email. One file, updated weekly. If your tool has a connector you can add it later.
2Build the aging list
Ask Claude to sort open invoices into buckets: not yet due, 1 to 30 days late, 31 to 60, over 60. Add totals per bucket and the top five amounts at risk. This one table is often the most useful finance view an owner can have.
Read finance/open-invoices.csv. Build an aging report with buckets: not due, 1 to 30 days late, 31 to 60, over 60. Show totals per bucket, the five largest overdue invoices, and any client with more than one overdue invoice. Save it as finance/reports/aging-YYYY-MM-DD.md.3Define a reminder ladder
Write the rules once: a friendly nudge at 3 days late, a firmer reminder with the invoice attached at 14 days, a call from the owner at 30 days, and a formal notice at 60 days. The agent drafts the written steps; the phone call stays human.
Create finance/collections-ladder.md: day 3 friendly nudge, day 14 firm reminder with invoice details, day 30 flag for a personal call from me, day 60 formal notice using our terms. Our tone is warm, direct and never passive-aggressive. Include a rule to never send more than one reminder per week to the same client.4Draft this week's reminders for approval
Each week, Claude drafts the reminders due according to the ladder, personalised with the client's name, invoice details and history. You read, tweak and send, or approve them for sending through your email tool.
Using the aging report and finance/collections-ladder.md, draft every reminder due this week. Personalise each one with the client name, invoice number, amount and due date. List the clients who need a personal call from me with a one-line note on each. Save drafts in finance/drafts/collections. Do not send anything.5Track promises to pay
When a client replies with a date, log it. Next week the agent checks whether the promise was kept and adjusts the next step. Promises that are broken twice go straight to your call list.
Here is a truth that hurts: many small businesses are not short of sales, they are short of collected sales. Owners hate chasing money, so reminders go out late, or in a tone that is either too soft or too sharp, and 30 days quietly becomes 75.
An agent does not mind chasing. It can read your open invoices every week, build an aging list, and draft a reminder whose tone matches how late and how important the client is. You approve each message in a minute. The chasing becomes a routine instead of an awkward decision.
Key points
- Unpaid invoices are a process problem before they are a client problem.
- An aging list is the finance view every owner should see weekly.
- A written reminder ladder removes the awkward decisions.
- The agent drafts; a human approves anything that goes to a client.
Avoid
- Sending reminders automatically before the ladder has been tested.
- Using the same tone for a two-day delay and a 60-day delay.
- Chasing a client who already paid because the export was stale.
- Letting the agent threaten legal action, which is always a human decision.
A 12-person marketing agency in Manchester had an average of 52 days to collect, with around 38,000 pounds typically more than 30 days late. The finance lead set up the reminder ladder and approved Claude's drafts every Monday in about 15 minutes. Three months later the average was down to 34 days, and the owner only made four personal calls in the whole quarter. Clients commented that the reminders felt more polite than before, because they arrived early instead of angry.