Late Invoice Chaser

Late-Invoice Chaser

Freelancers and small businesses lose more to unpaid invoices than to bad pricing — and the reason is usually awkwardness, not the client's cash flow. A calm, escalating sequence removes the awkwardness: each message is warmer than you feel and firmer than the last, so you get paid without torching a good client — and you have a clean paper trail if it comes to that.

What This Skill Produces

• The staged sequence — 4 messages tuned to how overdue it is: friendly nudge → firm reminder → final notice → next-steps letter
• The timing plan — when to send each, based on your terms and days overdue
• The levers — when to mention late fees / interest (if your terms allow), pausing work, or withholding deliverables — and how to phrase them without a threat
• The record note — what to keep (invoice, terms, delivery proof, every message) in case it goes to a formal demand or small claims

Required Inputs

Ask for these if not provided:

• The invoice — amount, invoice date, due date / payment terms, and how overdue it is now
• The relationship — long-standing good client, new client, or already rocky
• Your terms — do they allow late fees/interest? Is more work in flight you could pause?
• What's happened so far — any replies, promises, or silence
• Your goal — keep the client and get paid, or get paid and move on

Framework: Warm, Then Firm, Then Formal

1. Assume the best first. The opening nudge treats it as an oversight — most late payments are. A friendly "just floating this to the top of your inbox" often works alone.
2. Escalate tone on a schedule, not on emotion. Each step gets firmer and more specific (invoice #, amount, days overdue, a clear pay-by date) — driven by the calendar, not by how annoyed you are.
3. Make paying the easy path. Re-attach the invoice, restate the amount and methods, and give a specific new due date in every message. Remove every reason to delay.
4. Introduce consequences factually. Late fees (only if your terms allow), pausing active work, or holding final files — stated as policy, not punishment: "per our terms, invoices 30 days overdue accrue…".
5. Keep the record clean. Save the invoice, the agreed terms, proof the work was delivered, and every message. If it reaches a formal demand or small claims, this is your case.

Output Format

Chasing: invoice [#] · [amount] · due [date] · [N days overdue] · [relationship]

Send schedule

1 · Gentle nudge

[Warm one-liner, invoice re-attached, amount + new pay-by]

2 · Firm reminder

[Invoice #, amount, days overdue, specific date, payment methods]

3 · Final notice

[Clear pay-by, the lever: late fee / paused work / held deliverables — as policy]

4 · Next steps

[Factual: what happens next — formal demand / small claims / collections — with a final chance to resolve]

Keep for the record: invoice · signed terms/agreement · delivery proof · every message + reply.

Quality Checks

• The first message assumes good faith and is genuinely friendly
• Each step is firmer and includes invoice #, amount, and a specific new pay-by date
• Late fees are only invoked if the stated terms allow them
• Consequences are phrased as policy, not threats
• Timing is tied to days overdue, not emotion
• A record-keeping note is included for the formal path

Anti-Patterns

• Opening angry — a hostile first nudge burns a client who simply forgot.
• Vague reminders with no invoice #, amount, or date — easy to ignore.
• Empty threats — mentioning small claims you won't pursue weakens every future message.
• Inventing late fees your contract never specified.
• No paper trail — chasing by phone only, with nothing saved for a formal claim.

Example Trigger Phrases

• "A client is 3 weeks late on a £2,000 invoice — write me the reminders."
• "How do I chase an unpaid invoice without losing the client?"
• "They keep promising to pay and don't. What's my next message?"
• "Invoice is 45 days overdue and they've gone silent — what now?"
• "Write a firm final notice before I take this to small claims."