Teamwork Lessons I Learned The Hard Way ... So You Don't Have To

For any entrepreneur, management skills can make or break a business. These tips will help you keep your team engaged and productive.

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By Mike Kappel


Opinions expressed by Entrepreneur contributors are their own.

Early in my career, before I became my own boss and the CEO of Patriot Software, I was a hard charging mover and shaker. I did whatever was necessary to get the job done. I took no prisoners, offered no quarter to failure, and if my co-workers couldn't keep up, I left them behind.

However, in the process of getting the job done, I often ran over my peers. I had no patience for people who learned slower than I did. I had no patience for people who worked slower than I did. I deemed them to be lazy, ignorant, and a waste of the company's resources. I'd show my intolerance in my day-to-day actions by being short with them, not listening, and trumping their ideas with my own.

Instead of building up my coworkers and giving them encouragement to do better, I "wouldn't waste my time with them." After all, my time was much too valuable. I had places to go, and they didn't, or so I thought. I was the superstar, a self-given title that I measured with my own internal metrics, most of them woefully flawed.

How you get results matters.

I felt that it was only my results that mattered, and they were so good that people would see them, and them alone. I didn't realize it at the time, but, my personality was a problem for my peers, my department, my company, and for myself.

You see, I was excellent at smaller projects that I could do alone. However, projects involving other people were a problem because I either steamrolled them, ignored them, or didn't help them. These projects weren't fun for me nor for my peers. Worst of all, the project, the department, and the company suffered because our "team" couldn't function as a team— because of me. I wanted to be the quarterback, the front line, and the tight end. Although my intentions were good, this was bad for everyone. I got results, sure, but at a great cost. When promotion time came, I was passed over for lesser performers who could work with and manage people.

I needed to learn how to collaborate, delegate, and most of all trust my coworkers, even if I didn't think they could perform at the level I could. That's a fear many workers have, and it reflects arrogance and insecurity. The best way to deal with this fear is through helping and empowering teammates by building them up and supplying them with the tools, information, and resources they need to perform. A well-performing team is always more productive than a well-performing individual.

Related: The 6 Secrets for Turning Hard Work Into Elite Results

Anchored to the work.

I learned another lesson after my team projects ended. Since I was "THE star" with "THE knowledge" (which I didn't share with anyone else), no one else could support the project after it was completed. Hence I was tied to the project for a long time and couldn't move on to other projects.

When I say I didn't share, I mean I didn't document things, and I didn't help others understand what the project was all about. I ran so far out in front of everyone else that I was the only person who understood the project. Which means I was the only one who could fix it when it broke. After I worked on several projects in this way, I had no time to work on anything new because all of my time was spent maintaining the older projects. I thought I'd made myself invaluable, and irreplaceable, but I had really just painted myself into a corner.

You might think that if you're the only one with all the answers, you have job security and a golden ticket to a higher salary. Wrong. Just the opposite is true.

In my experience, people who covet information and don't or can't share with other employees are bad for business, and eventually are replaced or moved into less critical functions. They create bottlenecks that can choke the whole company.

Related: The 10 Communication Skills Every Entrepreneur Must Master


I think I started learning this lesson when something unusual happened to me. The company hired a younger, brighter, harder-working superstar than me. He was a better programmer, and he worked longer hours. He quickly caught the eye of management, and he was able to run circles around me. I figured, no problem, I'll catch up with him and regain my status. Well, he didn't give me the chance. He did to me exactly what I had done to my peers, only worse.

This new star didn't communicate to me the things he was learning. He hoarded knowledge. He ran over top of me. He made me feel inferior. He treated me poorly, ignored me, and chastised me. He basically gave me a taste of what I had given to other people. As if that wasn't bad enough, he went further. He actually sabotaged my work and sometimes played tricks on me with my work-related projects. Doing this was about as unprofessional as it gets, and management felt the same way.

He also talked down about me to my peers. He talked down about me to my bosses. He successfully made me look stupid and lazy to many people. Yet, at the same time, he made himself look like an immature, inflexible liability to management.

Management is always watching.

The best lesson learned through all of this was realizing that my bosses knew what was happening. Even though they only saw me a couple times a day or week, they knew my true nature and my true potential. They recognized how immature this new superstar was, and they were watching me to see how I was going to react. They wanted to see if I would be immature enough to stoop to his level and sabotage his work and play tricks on him, or if I had grown up a little. Fortunately, I had. I minded my own business, worked hard, and I let the new superstar be a jerk until he cornered himself in a dead-end position within the company. He later quit the company when he had burned every bridge.

Related: 19 Regrets Most Entrepreneurs Eventually Face

The benefit of hindsight.

20/20 hindsight is an amazing thing. Now, after 30+ years of aging (gracefully, I might add) and having hundreds of employees work for me at Patriot Software, I have had time to reflect on the people issues detailed above. I now realize those team players that I steamrolled or ignored had much to offer but I judged them too quickly. I hurt these people, our relationships, my department, my company, and my own career. Now I do my best to make sure that my young employes at Patriot Software don't display the same shortsightedness I did. I want them to have long and productive careers, with people they care about, and care about them. I want you to have the same.

I learned the hard way. Hopefully, you won't have to. Good luck.

Mike Kappel

Entrepreneur Leadership Network Writer

Serial Entrepreneur, Patriot Software Company CEO

Mike Kappel is a serial entrepreneur, and the founder and CEO of Patriot Software Company, and its subsidiaries.  Patriot Software, LLC is a developer of online payroll and accounting software for U.S. small-business owners.

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