How to chase a late payment

Most late invoices are not being refused. They are sitting in an inbox behind four hundred other emails, or waiting on an approval nobody told you about. The people who get paid fastest are not the most aggressive — they are the ones who make paying easy and ask early.

Here is the sequence, with the emails.

Before it is late: the day you send it

Two things move an invoice from 60 days to 15, and both happen at the start. Put an actual due date on it — “Due 14 September 2026”, not “Net 30” — and send it the day the work finishes rather than at month end. An invoice that arrives while the work is still fresh gets approved by someone who remembers it.

Three days after the due date

Assume it was missed, because it usually was. No apology, no accusation, and reattach the invoice — asking someone to go and find it is asking them to do work.

Subject: Invoice INV-0042 — due 14 September

Hi Sarah,

Just checking this one reached the right place. Invoice INV-0042 for $2,400 was due on 14 September. I have attached it again in case it is easier.

If it is already in the run for this week, ignore me and thanks.

Best, Shishir

“If it is already in the run, ignore me” does a lot of work. It gives them an easy reply and keeps the relationship intact.

Two weeks late: find the blocker

By now the question is not whether they saw it. Something is stuck, and your job is to find out what. Ask a question that can be answered in one line.

Subject: INV-0042 — anything you need from me?

Hi Sarah,

INV-0042 ($2,400) is two weeks past due. Is there anything outstanding at your end — a PO number, a different billing address, or someone else I should be sending this to?

Happy to reissue it in whatever form is easiest.

Best, Shishir

This one surfaces the real reason more often than anything else, and the reason is almost always administrative: the invoice needed a PO, or it went to a person who left.

Thirty days late: go around, politely

Your day-to-day contact is often not the person who releases money. Ask them to introduce you to whoever does, rather than escalating over their head — you want them helping you, not defending themselves.

Hi Sarah, this one is now 30 days over. Could you point me to whoever handles payments directly? Happy to take it up with them so it stops landing on your desk.

Forty-five days: change the register

Now it is a business matter and the email should read like one. Short, factual, dated, with a specific next step. State the interest if your terms carry it.

Subject: Overdue account — INV-0042

Hi Sarah,

INV-0042 for $2,400, issued 14 August and due 14 September, is now 45 days overdue. Our terms carry 2% monthly interest on overdue accounts from today.

Could you confirm a payment date by Friday? If there is a dispute about the work I would rather hear it and resolve it.

Best, Shishir

Inviting a dispute is deliberate. If one exists you need to know; if none exists, saying so removes their last comfortable reason to delay.

Sixty days and beyond

Options, roughly in order of cost to the relationship: a formal demand letter, a collections agency (typically 20–40% of what they recover), or small claims court, which in most of Canada and the US handles amounts up to $25,000–$35,000 without a lawyer.

Before any of that, weigh it honestly. Chasing $600 through court costs more in your time than the $600. Chasing $12,000 does not.

What actually prevents this

• A payment link on the invoice. Retyping bank details is friction, and friction is measured in days.
• Deposits on anything substantial. 50% up front filters out the clients who were never going to pay.
• An invoice number they can quote. Untraceable invoices sit.
• Written terms before you start. Not a contract necessarily — an email saying what you will do, for how much, payable within 30 days, is enough to hold up.

The Bindery invoice generator puts a real due date and a payment button on the document, which are the two things that move it up the pile.