Overdue invoice reminder emails for every stage, before invoices go stale

Most overdue invoices get paid after one clear, polite reminder. The problem is that nobody sends it on time. This lists every overdue invoice by age and drafts the right reminder for each stage.

By The Workshaped Lab·Autonomy: suggest·Prompt tested 14 Oct 2026
Accounting export (CSV)Any chatbotn8n (optional)
Who it's forAgencies, consultants, contractors and anyone who invoices clients on terms.
AutonomySuggest. Nothing is sent, posted or booked without a person.
TierWorkflow integration
ProvenanceIdea, prompt tested on synthetic data.

The problem

Small firms wait 30–60+ days for money because chasing is awkward and easy to postpone. By the time someone looks, invoices are 90 days old, the contact has changed, and some are past dispute or claim windows.

Why it works

Who is overdue and by how much is arithmetic from your accounting export, done in a sheet or code. The model writes the reminder in the right tone for the stage (friendly at 7 days, firm at 30, final at 60), using only the facts from the export. A person sends it.

The rule we build by: the model reads; code decides anything involving money, dates, matching or what's true; a person approves.

Step by step

  1. Export open invoices: client, contact, invoice number, issue date, due date, amount, amount paid.
  2. Calculate days overdue and group: 1–14, 15–30, 31–60, 60+.
  3. Draft one reminder per invoice matching its stage; include invoice number, amount, due date and how to pay.
  4. Flag disputes, partial payments and clients with several overdue invoices for a call instead.
  5. A person reviews and sends; log the date sent.
  6. Re-run weekly.

Pitfalls to avoid

  • Partially paid invoices: chase the balance, not the full amount.
  • One reminder per client, not per invoice, when a client has several.
  • Check payments received in the last few days before sending, so you don't chase someone who just paid.
  • Don't threaten late fees your contract doesn't include.

Free · Kickstart prompt

Get a rough first version today

Paste this into Claude, ChatGPT or Grok with your own data. It gets you a useful first pass, not the tested setup.

Act as a polite but firm accounts-receivable assistant. Today is [DATE].
Here are my open invoices (client, contact name, invoice number, issue date, due date, amount, amount paid):
[PASTE]
1. Make a table: client, invoice, balance due, days overdue, stage (1–14, 15–30, 31–60, 60+). Group clients with several invoices together.
2. Draft one email per client (not per invoice) matching their oldest stage: friendly reminder, firm reminder, or final notice before I call. Include invoice numbers, balances, due dates and [PAYMENT LINK OR DETAILS].
3. List any client I should phone instead (60+ days, partial payments, or a note that suggests a dispute), and don't draft an email for them; give me 3 talking points for the call instead.
Put the phone list first, then the emails.
Use only the facts above. Don't mention late fees or legal action. Show your days-overdue arithmetic so I can check it.
Check every result by hand. Don't paste account numbers or anything you don't need to share.

✓ Prompt tested 14 Oct 2026: we ran it with gpt-5-mini on a synthetic sample and checked the output by hand.

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