“Fred, you know, while you were in the hospital, I thought I would hold off on billing for the work I already did, out of respect for your situtation. I really hate to bring this up, and I know you’re dealing with a number of issues right now, but your account with me has some outstanding invoices.
Like I said, I wanted to wait until you were on the mend to trouble you about this, but I’d like to clear the backlog in your accounts before we press on with new business. Can we make some kind of arrangements to clear this old stuff out, so we can press on to do some new things together? I’m really flexible about the terms, just so we reach an understanding”
Aaron, I don’t think this is a moral dilemma so much as a social one of politeness and of business ethics. You are expected in most cases to ask for payment for work performed, and he is expected to pay. Now, there may be extenuating circumstances and hardships he’s facing, and you could, if you wish, choose to modify his debt or waive it, depending on your conscience. That’s a business decision on your part.
If you’re pretty sure he can’t afford to settle the old accounts in one go, and you can’t afford to just declare the loss, I would say, the gentlemanly thing might be to offer some easy, no-interest terms on a calendar of make-up payments, some schedule that he CAN meet.
Any time you defer payment until completion, you are extending credit. How much and for how long is up to you and the usury laws. If he’s in too bad of shape to pay up his backlog, it seems a poor investment to extend further credit for new projects. If you’re working in such a way that he’s always paying you Tuesday for a hamburger today, I think that’s not a very safe way to operate, even if he never misses a payment.
If you know this guy and he’s a long-time friend, you may feel it worth the risk, and if he’s truly a good guy, giving him the benefit of the doubt now, will often pay back multifold later in life, when he’s rich, because he knew you “back when” as loyal and fair.
…Or he may deny he ever knew you. That happens too.
We really don’t know your situation with this guy as well as you do. Decide how much you can afford to gamble and lose on this guy, if it doesn’t ever work out. Set that number down in writing in a note to yourself on the calendar. If he hasn’t made good on at least *some* of the debt by then, well, business is business. You are not a bank.