A client who won’t pay is a client who has stopped treating your invoice as a real obligation, and the fix is a sequence of steps rather than one hard conversation: check your contract, stop future work, revoke access to what you’ve delivered, and add a late fee.
Somebody wrote into the Idea Slam mailbag with this exact situation: a client they actually like is two months behind and keeps saying the check is coming.
What does “the check is coming” actually mean?
In eight years of running my own business, “the check is coming” has almost never been true. When a check is genuinely coming, people tell you the details without being asked. They say they cut it Tuesday through their bank and it should land in three to five business days. That’s a real answer, and you can plan around it.
“The check is coming” with no bank, no date, and no amount usually means the check hasn’t been written yet. It’s a way of ending an uncomfortable conversation without giving you anything. Once you learn to hear the difference, you stop waiting on the vague version and start acting on it, which is the whole point.
When should you stop being nice about a late payment?
Two months is well past the line. At 60 days behind, something has changed, and it isn’t a filing error. Either they no longer value the partnership, or they’re drowning, or they’re out of money. All three of those are their problem and not yours, and none of them get better because you waited another month to say something.
Being direct here isn’t being unkind. You can be warm to somebody and still tell them they owe you money, and the people worth keeping as clients will respect you for saying it plainly. The version that damages the relationship is the one where you say nothing for four months and then explode. Thirty days past due is worth a direct conversation. Sixty days is where you stop new work and start the steps below.
What are the steps when a client is behind on payment?
Go in order. First, read your contract and find the payment terms, because that document tells you what you already agreed to and what happens when it’s broken. Second, stop all future work immediately. There’s no reason to keep producing for somebody who is 60 days behind. Third, revoke access to the work you’ve already delivered. If you’re sharing Google Docs, unshare them. If they’re in a Slack channel or using skills and files you built, turn that off and tell them access comes back when the account is current. Fourth, start adding a late fee. Something changes when a 10 percent late penalty enters the conversation, and checks that were mysteriously stuck in the mail tend to arrive before the deadline.
All of that works better when it was agreed to in advance. If you don’t have a contract that spells out due dates, late fees, and what happens when an invoice goes unpaid, that’s the actual takeaway. Get one in place before the next project starts.
Should you keep working with a client who pays late?
Sometimes, if it’s a one-time thing with a real explanation and they make it right. But if you’ve run the steps and they still aren’t paying, that relationship is finished, and continuing it just costs you money and attention.
One more note worth saying out loud, since it applies to all of us as buyers too. There’s rarely a good reason to be two months late paying a vendor. Credit cards exist for exactly this. Owe Visa, owe American Express, and leave your small vendors out of it. When a client is 60 days behind on me, I’m the one with a payroll problem. I’m not a bank, and neither are you.
Questions owners ask
How much should a late fee be?
Ten percent is a common figure and it’s large enough to change behavior. Whatever you choose, it should be in your contract before the invoice is late, and you should apply it consistently.
Can I take back work a client hasn’t paid for?
You can revoke access to anything you control, like shared documents, shared workspaces, and ongoing services. What you can do about work already fully handed over depends on your contract and your local law, so ask your attorney.
How do I ask for money without damaging the relationship?
Be specific and unemotional. Name the invoice, the amount, the original due date, and what happens next if it isn’t paid by a date you choose. Vagueness is what makes these conversations feel bad, not directness.
Should I offer a payment plan?
If the client is honest about being in trouble and you want to keep them, a written payment plan with dates is better than an open-ended promise. Put it in writing, stop new work until they’re caught up, and treat a missed plan payment as the end of it.
Here’s the homework. Open your invoicing and find anybody past 30 days. Send one specific email with the invoice number, the amount, and a date. Then watch the full episode for the whole conversation.
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