Should You Do Business With Friends?

As more people do business from home, I’m seeing an increase in friends doing business together. Many of them have asked me my thoughts on whether they should – or should not – do business with friends. A case in point is the reader who recently sent me an email saying that she did business with a friend, and now there are problems with the expensive item she purchased. She goes on to say that she hopes her friend will “step up to the plate” and make it right, but if she doesn’t, it would end their friendship or at least make things awkward. What started out as a pleasant interaction has now become an uncomfortable situation.

So let’s walk through this: Why are we friends with people? Usually it has something to do with trust and respect. You don’t initiate and maintain a healthy friendship with somebody unless you have trust and respect for him or her.

In answer to the reader’s email: Your friend sold you something that malfunctioned or isn’t a good product. If you judged her correctly in making friends with her, and she deserves your trust and respect, then she will be just as disappointed in herself (or whoever made the product) as you are. Keep in mind that for you it’s only one purchase. But for her it’s her livelihood and the reputation of her store or service. By the way, all of this would still be true whether or not you were her friend.

If something about her made you want to be friends in the first place, then she deserves even more benefit of the doubt than if you weren’t friends. My suggestion is that you don’t let any more time pass before you approach her and simply tell her what happened. If she’s the friend you assume she is, she’ll jump at the chance to show you that she’s worthy of your trust and respect.

I say all this because it sounds like you’re worried about losing the friendship over this. Your letter suggests that if she doesn’t handle this right, it will be the end of your friendship. But, wait: If she handles it badly, why would you want to be friends with her anyway? Isn’t it just as likely that she holds your friendship in high enough regard that she’ll do everything possible to make things right? Unless you’re a terrible judge of character, it seems reasonable that she’ll most certainly “step up to the plate,” as you say.

The two of you will come out of this with one of two outcomes: Your friendship will either be stronger, or you will experience a disappointment deeper than a normal bad business experience. Why? Because you’re not only stuck with a bad purchase, but you saw your supposed friend’s true colors when it mattered most and realized that you judged her incorrectly.

I know that everyone says you should never do business with friends, and that might be true. After all, friendship and business relationships are two completely different things, with a completely different set of expectations. But I suspect what’s closer to the truth is that doing business with friends is risky. Money stirs up primal feelings and emotions as basic as self-preservation. These emotions don’t normally come into play in a friendship, but when you’re dealing with money you learn more about people than you otherwise would. As they react to those primal emotions within the context of friendship, you see their true character and personality for what they really are – or are not.

Again, that would be true whether or not you were friends. So I urge you to politely confront her and give her the opportunity to show you her true colors and demonstrate just how important your friendship is to her. Sure, that’s risky, and there’s a lot riding on it. But if you picked your friend wisely, then both of you will be better for it.