Chasing payment badly costs more than the payment. A customer handled aggressively over a small late installment will not return, will not refer anyone, and may well dispute the debt out of resentment rather than inability.

Firmness and courtesy are not in conflict. Here is how to hold both.

Make the first contact early and neutral

Contact on day one or two, before the amount feels serious to either side.
The tone: Assume it was an oversight, because usually it was. A short factual message naming the amount and the date resolves the majority of late payments with no friction at all.

Ask before you assume

The second contact should be a question, not a warning.

• Ask: Has something changed that makes this schedule difficult?

• Then listen: A customer who tells you their income dropped is giving you the information you need to recover the money. Rescheduling at that moment usually recovers far more than enforcement started three months later.

Escalate on the written path, on time

When escalation is warranted, follow exactly the steps set out in the agreement and no others. Predictability is what makes escalation legitimate , the customer agreed to these consequences, in this order, at signing. Improvised pressure outside that path is what turns a recoverable debt into a dispute.

Keep the door open

State plainly what would resolve the matter and how to do it.

• Confirm in writing when a customer settles, and say so plainly.

• Restore a good customer's terms once they are back on schedule.

• Most people who fall behind intend to pay. Treating them as though they do not is the fastest way to make that untrue.