Confessions of an Entrepreneur: Some of My Biggest Regrets as a Leader

I have plenty of accomplishments over the course of my career that I’m proud of. But I also have plenty of regrets. While I don’t let my many mistakes take up too much of my mental real estate, I do believe that one has to acknowledge them so they can learn and not repeat them in the future. Especially when it comes to leadership. 

Since the title of this series of blogposts is “Confessions of an Entrepreneur,” it’s probably time to make that title real and offer up some of my confessions. So here we go, in no particular order of importance:

1.  I wasn’t open enough to new thinking brought to me by my team.

I was so certain of our mission and strategies, that I was very intolerant of anything that contradicted or conflicted with those in any way. I was also just resistant to changing systems that I felt worked well as they were. Our prior, consistent growth and profitability was always my justification for my resistance to change. I’m sure I turned off some good people and shut out some good ideas because of that.

2. I was too judgmental and quick to write off certain employees.

In some cases, just a single infraction of the rules—written or unwritten—was all it took for me to decide that someone was not good and shouldn’t be on our team. That was probably too harsh.  I should have been more tolerant and less quick to pronounce a sentence. 

3. I was way overcommitted and failed to do many of my jobs properly.

This was undoubtedly one of my greatest sins. My philosophy was basically this—I would never have to motivate myself as long as I overcommitted and was a responsible person. I figured I would always “rise to the occasion.” But the problem is I wasn’t always able to devote adequate time and attention to things that were the highest priorities for the business. I tried to do everything but ended up doing nothing very well.

4. I did not give anyone my full attention—ever!

I was one of those people who would often be in a meeting and yet constantly looking at or responding to people on my phone. Or if someone was in my office, I could be simultaneously doing stuff on my computer.  It’s so rude. It’s embarrassing that I was so disrespectful. I rationalized that I had to multi-task because I was so busy. But the fact is you can’t treat other people like that and expect them to think you really care about them.  As a wise person once said to me, “Your actions are so loud I can’t hear what you are saying.” Apropos in my case, for sure!

5. I let some managers who were destroying the morale of their people go on too long.

You might ask why I would do this?  There are three reasons. One, the manager could have been a high performer in terms of the revenues they and their team were bringing in. Two, I always felt that I had to let managers run things the way THEY wanted to, or they would no longer be accountable for the performance of their team.  And three, I avoided confrontation with my managers. None of these is a valid justification for letting them mistreat someone or making people feel bad such that they were demotivated or would leave the company.

6. I let some of my top leaders run off other good people because of favoritism.

I never should have let this happen. You cannot allow managers to have a popularity contest. Promotion has to be based on merit, not how much your boss likes you—especially when there are other people in your unit who are outperforming you. I will never forget losing one of our highest performers in a department because the manager simply liked someone else who worked for him better. The other guy was more fun to hang out with whenever they were in the same city together but wasn’t as good of a performer as the one who quit in a rage when the other guy got promoted to a role he should have gotten.

7. I was way too hard on some people.

Combined with my typically laissez-faire management approach, I also occasionally went the other way and micro-managed those people who had done something that made me lose confidence in them.  That not only took up too much of my time and mental energy, I also ended up demotivating the person I was doing it to.

8. I let some cancerous high performers stay on too long.

This is always a toughie—you have someone who is bringing in a lot of revenue, but they are damaging the morale of everyone else in the organization because of either their negativity toward the company and management or because they were credit and glory hogs. Either way, it’s not worth it. I would rather have a good performing team of ten with generally happy and motivated people than a “rock star” and nine discouraged and unhappy people, any one of whom has the potential to infect ten other people with their attitude!  It’s just bad business.

9. I was down on anyone who left the company and could have spoken disparagingly about them, especially if they wanted to start their own business or go to work for a competitor.

In my mind (at that time), those people were joining the enemy.  But that was a bad approach. The fact is, any one of those people could have also brought work back to us in the future, or even come back to the company at some point if I ever acted like that could be a possibility. I never went to the “going away” lunches for anyone; it made me mad they quit and upset that we were celebrating their departure. I thought we should be having “staying lunches or parties” instead. It was a mistake. 

I’m sure if I kept this blogpost in my drafts, I could probably list another nine (or more) mistakes I frequently made as a manager or leader over the last 40 years! The important thing is, however, to learn from one’s mistakes so you don’t repeat them in the future!  And that, my friends, is something that I AM fully committed to!