Best strategies to send payment reminders for overdue invoices

I’ve got a client who’s 45 days overdue on a significant project. I’ve already sent two reminders, but it’s like I’m talking to a wall.

I can’t help but think if I’m being too nice or not assertive enough. How do you guys manage the tricky balance of pursuing overdue payments without ruining the relationship?

At 45 days I would add interest charges to the next invoice if your contract allows it.

Some clients need to feel consequences before they take you seriously. I also mention that future projects require payment upfront when someone goes this far overdue.

The relationship is already strained when they ignore you for weeks.

Most people wait too long to make the call. Phone beats email every time when money gets involved. I call after 30 days, not 45. When you get them on the phone, ask for a payment date right then. Not ‘when can you pay’ but ‘can you pay by Friday or do you need until Monday.’ Make them pick a date. If they miss that date, you know they’re playing games and can move to collections without feeling bad about it.

Stop being nice about it. 45 days is way past reasonable.

Here’s what I do when clients go radio silent:

  • Send a final notice with a clear deadline (like 7 days)
  • Add late fees if your contract allows it
  • Put all other work on hold until they pay
  • Be direct: “Payment is now 45 days overdue. Please remit immediately.”

If they don’t respond to the final notice, start looking into small claims court or a collections agency. The relationship is already damaged if they’re ignoring you for this long.

Don’t chase bad clients. Your time is better spent finding ones who actually pay.

After 45 days I’d call them directly. Email gets ignored too easy.

I would just keep sending reminders until they pay.

Had this happen with a client who owed me $8,000. Went 60 days without paying.

What finally worked was changing my approach completely. Instead of asking for payment, I started asking what the problem was. Sent an email saying “I’m concerned there might be an issue with the invoice or the work. Can we talk?”

Turns out they were having cash flow problems and were embarrassed to say anything. We worked out a payment plan and I got paid in full over 3 months.

Sometimes clients go quiet because they’re stressed about money, not because they’re trying to screw you over. Worth one conversation before you go nuclear on them.

If they still won’t talk after that, then yeah, time to get tough.