Confessions of an Entrepreneur: Leadership Lessons Learned

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I certainly understand the adage that the older you get, the more you realize what you don’t know. I am painfully aware of that in many different areas of my life. But that said, the last 40-plus years as a student of business, management consultant and business owner have taught me something. Leadership — the quality of it — is the special sauce that makes everything in the organization come together.

Here are some of my thoughts on leadership that may be helpful to anyone who owns a business or who is running one:

• Selecting who will be formally assigned a leadership role is never easy. But it may be easier than you think if you approach it differently. Instead of basing your decisions on seniority or the existing organizational hierarchy and who is next in line, do so instead on who is already demonstrating an ability to lead other people. I was reminded of this recently when a client in the professional services business skipped over all of their existing partners and elevated a younger and more dynamic person to the president’s job when the current president died suddenly. The person they picked is more energetic, committed and a better communicator than anyone in the partner ranks and is already taking the company in new positive directions.
• A person who is good at doing something is not necessarily going to be a good leader. The best salesman may not be the best sales manager, or the best engineer may not be the best leader of a team. On the other hand, try leading people who do something that you aren’t good at doing yourself and you will have problems! People do want to work for people who have been in their shoes and have some deeper understanding of the work itself.
• Good leaders realize that no one has to do what they are told to do. People have free will. You can own the business entirely or even be majority owner, or someone can report to you officially as their manager, but none of it matters in the end because people have free will. If they don’t like or respect you, they will not listen to you, and they won’t do what you want them to do. More people in leadership roles should understand this.
• No one will respect you as a leader if you yourself don’t do everything that you expect them to do. For example, in the architecture and engineering industry that I come from, firm partners are often frustrated when their people won’t turn their timesheets in on time. Billing of clients is based on these time sheets and if they aren’t completed, the firm cannot get paid. In spite of this fact, do you know who I find are usually the worst offenders? The partners themselves! No wonder their people don’t see how important timely timesheet completion is. There are many more examples of this in every business. “Do as I do” has to be part of the leadership culture.
• Good leaders talk to people. They say “good morning” cheerfully to everyone. They ask the people they see in the hall or coffee room how their weekends were and how their family members are doing. They call and text their key people to check in when out of the office. They ask people out to lunch who are way below them in the pecking order. They walk around the office or store or shop floor. Talking to people is how you form relationships with other people. Sam Walton was a master at this!
• Effective leaders are good listeners. They focus on what someone is saying and devote their full attention while doing so. Try putting your phone down and actually listening to someone for 15 minutes. Odds are — if you are a busy business owner or manager like me — that this will be difficult at first. But you have to do it if you want people to think you care about them.
• Good leaders aren’t afraid to confront someone who needs confronting. This includes customers who are abusing employees, employees who aren’t doing their jobs and fellow partners or owners of the business who aren’t carrying their weight. They understand that other people need them to do this dirty work, and if the leader doesn’t do it, no one else probably will. If you are a leader, you may have to be the bad guy occasionally, and not everyone will always love you.
• The best leaders are helpful. They are willing to pitch in and do what is necessary for the organization to fulfill its mission and meet its goals. They help other people do their jobs. They clear roadblocks for other people. They get the resources and tools their people need to be more effective. They will do low-level tasks such as cleaning up the kitchen, or even a bathroom. There’s nothing quite like showing everyone nothing is beneath you if you want to endear yourself to them.
• Real leaders are hard workers. They are often the last person at the office each night. They also are sensitive to others who are putting in extra effort and working hard. They acknowledge those workers with thanks. Again, they have no expectation that someone else will do something that they won’t do.
• The best leaders develop other leaders. That takes a lot of time and coaching and demonstration of how to do things, and it doesn’t always work out. When it doesn’t work out, a smart leader will reallocate his or her time to help someone who may be able to learn from the lessons they have learned. No one will be as good as you are at doing some of the things you have to do — at first. But given proper time and direction and coaching — that is another matter. The person you are working with may actually become a better leader than you are!