Dear Dave,

My husband and I have run our own small business for nearly 10 years. Our largest client, who is also a friend, is almost three months behind on the bill. He has always been good in the past about paying on time, but we work on a 30-day payment period. Can you give us any advice on how we should handle this?

Melissa

Dear Melissa,

In my mind, there’s no reason to level accusations or make threats in a situation like this. There are personal dynamics involved, and my guess is he’s probably not trying to outright cheat you.

If it were me, I’d go to his office or ask him out to lunch, and then have a friendly sit-down talk. Listen to what he has to say about being so far behind with his bill, but at the same time you need to let him know that you can’t function as his bank. You’re a small business, and you need your money. Some kind of understanding and agreement have to be reached.

For starters, a fair request would be asking him to help things along by trying as best he can to get current on his bill as soon as possible. At the very least, he needs to do something to reduce the amount owed within 10 days. You’ve provided services for him, and you’re owed money that’s long past due, so there’s nothing wrong with this. I’d also establish an understanding that once he’s caught up on the past due amount that all payments for services going forward will be due within 14 days after delivery.

Now, he may not like this. If he pushes back too hard, you may have to switch to a cash-only basis with payment due on delivery. If it were me, and he didn’t like any of these options, I’d politely suggest he take his business elsewhere.

Like I said, he’s probably not a bad guy, just another small business person who’s disorganized. That’s not an uncommon thing. But you definitely need to correct this behavior before it gets any further out of hand. You’ve got a business and a livelihood to think about, too!

-Dave