Michael Riley | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Michael Riley


Boxter helps companies build web traffic online through targeted content marketing.

The Mistake:

Not going with my gut feeling about firing someone. It was the first time I had ever built a sales team. I really wasn't sure of myself. I read as many articles as I could, but you can't really understand the process until you've done it. One person, in particular, I felt that I would not buy what he was selling.

If I didn’t trust this guy and really believe what he was saying, why would anyone else? That was a real problem, but we still kept him around for another three or four months after that.

Another person was a designer we had. Even though he was a nice guy and everyone liked him, he was disruptive. He wouldn't shut up. He kept interrupting meetings with random ideas. We realized once we let him go that everyone was much more productive.

Growing a business is about relationships.

The Lesson:

As soon as you start to feel like it isn’t going to work out, it's best to go ahead and fire them. You can't waste time micromanaging employees. You need to have faith that they're going to get work done.

I've wasted so much time, money and effort on some people that weren’t a good fit. You want to have faith in them, you want to support them and think that they can learn, but if several months go by and there hasn’t been improvement and you're still feeling that way, you should cut your losses. You need to listen to your instincts.

Growing a business is about relationships. If you have someone that people don’t want to be around because they're annoying or because they seem slow, it’s not a good fit. 

You need to weigh things based on the role that needs to be filled. It's not so much whether you think they are going to perform well or not; we found that having a checklist of points doesn’t really work. Because they can meet all those and, at the end of the day, it still comes down to personality.

It’s not whether they have 20 years of experience or they worked for this company or what have you, it's more about, do we want to hang out with these people? Are these the people that we want to go have a beer with?

Follow Michael Riley on Twitter at @itsatechworld.