Do the Right Thing: Have the Hard Conversations - David DeWolf

Do the Right Thing: Have the Hard Conversations

800 533 David DeWolf

I’m the kind of guy who hates sending my food back to the kitchen when it’s not done the way I like it.

I get the argument that you’re in a restaurant and you’re paying for service and it should be done right, but there’s something about me that doesn’t want to complain. I don’t want to make the other person suffer because they didn’t do something perfectly or didn’t meet my expectations.

Maybe it’s the fact that I’m in the services industry and I get it. Sometimes there are just missed expectations, and they’re nobody’s fault, I just had a different idea than what they had. Every now and then, you overcook a steak a little bit. So what? I can still be grateful for it. I can still enjoy it, even though it’s not perfect.

Unfortunately, I have a situation right now that takes this to the next level. I have a good friend who, after years in technology, decided to start his own business. His business is one that I typically wouldn’t engage with, but this is a guy I really like. He’s personable, professional, does things well, and is a good all-around guy.

He’s a custom clothier. That’s right: he makes custom clothes. He helps you build a wardrobe that fits you well, feels good, and looks right. To be honest, I have no sense of style, so several months ago, I reached out to him. I said, “It’s finally time.” He’s never tried to give me a hard sell, but after seeing a couple of my suits fall apart, I thought, “You know what? Because I wear them so often, maybe it would be best to get something custom that will last a little longer.”

Unfortunately, this has turned out to be a disaster. I paid a good bit of money and a couple of the suits I purchased are good and solid, but several of the pairs of pants and a couple of the sports jackets are just falling apart. I’ve already had to send a couple of them back, and I’ve had buttons fall off pants and coats. I’ve had snags in the pants that just make them look bad. One of the pairs of pants, when I got them back after the snag was fixed, the butt was hanging to my knees.

It was ridiculous.

I do not have the guts to call this guy. I just do not want to send the stuff back.


In business I’ve learned to have blunt, hard conversations. I truly believe that by building a trust relationship and by openly discussing issues and problems, we all get better and we all solve problems. But for some reason, when I’m paying for a service, I struggle to take that same mentality.

On one hand, I know that this friend really needs to hear the feedback. On the other hand, I don’t want him to take the financial loss, and to do what is right would require a financial fix. Maybe it’s that I fear that he won’t do the right thing, but I know that he will. Maybe it’s that I fear that I’ll put him in a very difficult spot.

Whatever the case, I’ve found that, over and over, brutal honesty, with transparent and open communication, don’t just help you, they help the person you’re having those communications with.

I’m going to reach out and I’m going to take the action to go ahead and talk to my friend, to give him the feedback that he needs. I don’t need to be irate or upset, but I need to let him know that his business is not meeting expectations. I expected a superb product, and while I may have gotten it for a couple of suits, I sure didn’t get it for the rest.

This is beneficial for him just as much as it is for me. Sometimes you just have to will things over the line. Sometimes you just have to suck it up and do what’s right. In this case, it’s not about doing what’s right for me, it’s about doing what’s right for him.