Dealing with a client I’ve worked with for a while now, but they’ve got two invoices overdue. It’s tough since we have projects going on, and I don’t want to ruin the rapport.
For one-off jobs, I usually just let it go, but this client is different—the pay is good and I enjoy the work. How do you approach the money talk without it getting awkward?
Call them directly instead of sending another email. Most people avoid written reminders but will actually talk when you call.
Just say you need to clear up the outstanding invoices before moving forward with new work. Don’t make it personal or complicated.
I put new work on pause until overdue invoices get sorted. Been burned too many times continuing projects while chasing payments.
Here’s what works for me:
Yeah it feels awkward at first, but good clients understand. The ones who push back or make excuses usually aren’t worth keeping anyway.
If they’re truly good to work with, they’ll apologize and pay up quickly. Sometimes people just forget or have internal process delays.
I handle this during our regular project check-ins. When we’re discussing the current work, I bring up payment status naturally.
Something like “By the way, I need to get those two invoices cleared up - should I expect payment this week?” Works way better than formal emails that feel like collections notices.
I keep working on the current project but don’t start anything new until they catch up. Found this keeps the relationship smooth while protecting me from the balance getting too high.
Most clients appreciate the direct approach. They know they owe money and usually just need a gentle push to prioritize it.
Two overdue invoices would make me nervous. I’d probably mention it next time I’m there working.
Stop all work until they catch up. I learned this lesson after a client owed me three months and vanished. My rule now is simple: two overdue invoices mean everything halts. Send one clear email stating that work will resume when they settle up. Good clients will understand and pay quickly. Those who don’t were never worth keeping.
Just ask when you see them next time.