Just came across that tricky situation with a client who’s overdue by three weeks on a good invoice. Following up feels like a balancing act—trying to stay professional yet firm.
If I come off too strong, they’ll push back. If I’m too lenient, it drags on. Anyone else relates to this challenge of juggling assertiveness and maintaining a good relationship?
Just call and ask them about payment.
Three weeks is too long. You’re being too lenient.
I give clients one week maximum before I call them directly. Forget emails. Phone calls work better.
They owe you money. Stop worrying about hurting their feelings.
Been there with clients who drag out payments. Setting up a payment schedule from day one saved me.
I send invoices with clear terms - net 15 or 30. Automatic reminders go out the day before it’s due, day of, then weekly after.
Make it feel automatic, not personal. I tell clients upfront my system sends these so they know it’s just business.
For late payments, direct but friendly works: “Hey, checking on invoice #123 from last month. Any issues on your end?”
Usually they forgot or AP is swamped. Clients who get defensive about polite follow-ups? They’re problem clients anyway.
Just stop working until they pay. That’s the way to handle it. Can’t do work for free.
I add late fees to my contracts. They start after 30 days. It makes those payment conversations easier. Most clients pay up when they know there’s a penalty. The ones who don’t? They may not be worth keeping as clients.
I used to stress about this until I found my rhythm. Here’s what works:
Week 1 overdue: Quick email - did you get the invoice?
Week 2: Direct follow up with amount and due date
Week 3: Phone call or final notice
After that I stop new work for them. Not aggressive, just practical.
Biggest lesson? Don’t take it personally. They’re not trying to hurt you - could be cash flow problems, messy accounting, or they forgot.
I ask new clients about their payment process upfront now. Some companies have crazy approval chains that drag on forever. Knowing this saves headaches.
Most clients respect polite persistence. The ones who get pissy about reasonable follow ups? They’ve got bigger problems anyway.