Business leaders will often write thought-leadership pieces about mistakes they made earlier in their careers, and usually end with a positive outcome. But sometimes mistakes are just mistakes. And one of my biggest mistakes was holding on to an employee for too long. In hindsight, I’m confident I didn’t make some hires — while this individual worked for me — I should have for the fear of offending him, or was too concerned about what he was going to think. There were really strong candidates I should have hired because they could have driven our business, but I was hesitant to have them report to him. I had a great, young staff that was temporarily stunted while reporting to him.

He was a really good individual producer. He could sell, he could recruit, and was an overall good employee. However, he never evolved with my business. Despite the negatives that came with employing him for far too long, there was one positive that came from it: It showed my staff I was extremely loyal, and that goes a long way. This experience compelled me to create a training department because I truly wanted this employee to remain at my company. He was a good worker, but just in the wrong department. So I took a chance and opened a branch office for him to lead a new project. It failed, but it taught me that failure is okay, and it showed me how to go about doing the same task differently in the future.

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Holding on to employees — especially those that become friends — for too long is a huge challenge entrepreneurs face, because it’s not really a “business” issue. It isn’t about sales or marketing. It isn’t about expansion or operations. It’s about one salary. That’s how entrepreneurs always justify holding on to a pain in the you-know-what. It’s just “x” amount of money, I can afford it and it doesn’t affect the business. But it does.

Employees see you playing favorites. Even if you complain about the person, they see that person as having immunity — and that’s not fair. You spend countless hours at work and sleepless nights thinking about this person and what you “can do with them.” At the end of the day, if a relationship is severed because you had to do what was in the best interest of the company, then the relationship wasn’t strong to begin with.

I didn’t fire this person. He fired himself. He didn’t want to learn from younger staff who were faster and smarter than he was. I begged him to. He didn’t want to put in extra time to learn new skills and create new plans. I challenged him to. My biggest mistake? Thinking that everyone wanted to grow — including him — and hoping things would change. Hope isn’t a plan. It was tough to cut him loose; however, it taught me a valuable lesson and made me a better leader, manager, and person.