What's the best way to handle unpaid invoices without upsetting your clients?

I’ve got a client who’s 45 days late on a significant invoice. They’ve generally been great to collaborate with, so I’m hesitant to push too hard.

I tried a gentle reminder, but it feels like I’m talking to a wall. Am I being too lenient here?

Money talks louder than feelings. Call them instead of more emails.

45 days is way past gentle reminder territory. Send a firm but professional email stating payment is overdue and include a specific due date, like 10 days from now. Add late fees if your contract allows it. Good clients pay their bills on time. If they don’t respond to the firm notice, start considering whether this relationship is worth keeping.

You’re not being too lenient, you’re being normal. Most of us hate confrontation when it comes to money.

Here’s what works for me:

  • Send one more email with a clear subject line like “Invoice #123 - Payment Required”
  • Give them an out by asking if there are any issues with the invoice
  • Set a deadline - something like “Please let me know by Friday how we can resolve this”
  • Stop all new work until they respond

Sometimes good clients just get overwhelmed or their accounting department is a mess. But 45 days means something is wrong on their end.

If they ignore this email too, then you know where you stand. A client who won’t even acknowledge an overdue payment isn’t really a good client.

I learned this the hard way after a client owed me for three months. Now I have a process that keeps things professional but gets results.

First invoice gets sent with normal 30 day terms. At 15 days overdue, I send a “just checking if you received this” email. At 30 days overdue, I call and ask when I can expect payment. Most people pay after the call.

If they hit 45 days like yours, I send what I call my “business decision” email. I explain that I need to put the account on hold until we get current, and ask them to help me understand their payment timeline. This lets them save face while making it clear I’m serious.

The key is having your next steps planned out. Don’t just send one more email and hope. Good clients will work with you once they know you mean business.

I just show up and ask for payment directly.