The customer only ever pays after being chased

The scenario

This customer always pays — eventually. But never on time, and never without a phone call. The pattern is so consistent it has become a routine: the invoice goes out, the due date passes, you ring, they apologise, and a few days later the money arrives. You have stopped expecting anything different. The balance always clears, so it never feels like a crisis, but you are effectively running this customer's payment schedule for them, and every chase is time and cost you absorb for the privilege of being paid late for work you already did.

What's really going on

A customer who reliably pays only after being chased has worked out something important: your due date is not a real deadline, and the only deadline that matters is the one attached to your phone call. They are managing their own cash flow by holding your money until the last possible moment — using you as an interest-free source of working capital. It is rarely malice; it is simply that paying you late carries no cost to them, so why would they stop? The crucial insight is that this is structural, not occasional. Nothing in the current arrangement rewards paying on time, so nothing will change until you change the incentive.

Your options

Because the cause is structural, the fix has to change the underlying incentives:

• Make late payment cost something. Apply late-payment interest or fees where your terms allow, so delay is no longer free.
• Tighten the terms for this account. Shorter terms, a deposit, or payment on delivery removes the gap they have been exploiting.
• Reward early payment instead. A small prompt-payment incentive can shift behaviour where penalties feel too blunt.
• Automate the chase. Scheduled reminders that go out before the due date reduce your cost and pre-empt the lateness.

Recommended approach

Treat this as a terms problem, not a chasing problem. Have a direct, friendly conversation that names the pattern without blame: payment has consistently been a little late, and you would like to put the account on a footing that works for both sides. Then change something concrete — typically by enforcing your late-payment terms so delay carries a cost, tightening the payment terms for this customer, or asking for payment on delivery if the lateness is chronic. Pair that with automated reminders timed just before the due date, so the prompt arrives before the habit kicks in and you are no longer the customer's accounts-payable department. Watch the next two cycles closely; if behaviour improves you can relax, and if it does not you have a clear basis to tighten further. For the broader playbook on stubborn late payers, see handling stalls and excuses.

What to avoid

Do not simply accept the pattern as "how they are" — every cycle quietly transfers the cost of their cash management onto you. Do not keep relying solely on the manual chase, since that rewards the very behaviour you want to stop and consumes your time indefinitely. Do not apply interest or fees you never disclosed in your terms; charges must be grounded in the agreement the customer accepted. And do not escalate straight to harsh measures for a customer who does ultimately pay — the goal here is to reset incentives, not to rupture a workable relationship.