A long-term client asked if they can pay their latest invoice in two weeks instead of this week. I want to be flexible, but where's the line between being helpful and being a pushover?

After a great year of timely payments, they’re now asking for a one-week extension.

I get it, life happens, but I can’t shake the feeling that this opens the door for more delays. How do you find that balance?

Let it slide this time since they have paid on time before. Just remind them that late fees kick in after 30 days. Good clients can get a break, but make sure to reinforce that the payment terms stay the same with future invoices.

One week isn’t worth burning bridges over. Just say yes but track it.

When clients ask for extensions:

  • Grant it without drama - good payment history earns goodwill
  • Write it down - I keep a simple list of who asked and when
  • Watch for patterns - if they ask again in a few months, that’s conversation time

The real test is the next invoice. If they’re back to paying on time, you made the right call. If they keep pushing boundaries, you know they were testing you.

Don’t overthink one request from a reliable client.

A week’s delay works if you trust them.

Good clients earn some slack. Just mention payment terms when you say yes.

One extension’s fine for good clients, but make it clear this isn’t becoming the norm.

I say something like “sure, but we’re sticking to original terms going forward” when I agree to delays. Sets the boundary without being a dick about it.

Same thing happened to me. Regular client asked for an extra week to pay.

I said yes but asked why - turned out their big contract payment got delayed. Made me feel way better knowing the reason.

Now I always ask what’s going on when someone needs extra time. Most people are straight up about cash flow problems. If they dodge the question, that’s when I worry.

Since your client’s been reliable, I’d give them the extension. Just ask what’s happening - you’ll know pretty quick if it’s a one-off thing or something bigger.