Lessons I'm learning in leadership
Leadership is a complicated thing. It's easy to be a lousy leader. We've all dealt with them. We've all complained about them. But when you find yourself in that position, it's easy to see how they did so poorly. It's easy to doubt you are the right person for the job. Knowing if you're doing the right thing and making the right choices is more complicated. Your past becomes littered with mistakes, and it can be easier to wallow in them than to learn from them. I don't know what makes someone a good leader, but I read about, think about, and spend a lot of time working on it.
There's a cliche that the worst leaders are the ones who seek leadership. They aren't seeking leadership. What they are seeking are prestige, fame, and wealth. I like Orrin Woodward's assertion, "The greatest leaders are reluctant ones who lead because they realize that no one else seems willing to step up." That is the position I have often found myself in. Suddenly, I will look around, and people are looking to me for direction. It is rarely a conscious decision, but it is a pattern repeated throughout my life. But just because people are looking at you doesn't mean you are good at it.
When you are leading a team in something complicated, like building software, there are many things you need to do right. It starts with assembling the right team with the range of skills to solve the problems you will be facing. Understanding the strengths and weaknesses of each member and the complexity of each issue so you are giving the right person the right job is critical. Being ready to help people learn and understand something new to them is fundamental to their growth and yours as a team. That is not easy to do in practice, however. Those are all areas I am working to improve.
I have struggled to analyze people's skills and bring together the right group. I am still looking for an excellent way to reliably test a person's skills beforehand. Their results may look great up front, but cracks start to show as things get more complicated. Then, the quality of their work degrades. I often hear the advice to trust your first instinct when you don't believe someone is up to the task. I have yet to do that. I invest more, hoping to uncover what I saw there initially. It comes from caring about the person and wanting to avoid starting over with someone new. It would be easier to improve that person than find someone better qualified. That is a disservice to me. That is a disservice to everyone else on the team. That is detrimental to the outcome we are looking to achieve. I can only improve this through repetition (hopefully only a few) and mentorship. I need to follow the common wisdom. I need to find a sounding board who has made those calls before.
One area where I am confident is knowing what to do and how to do it. I always have a good idea of the work that needs to happen. I usually have a clear picture of how we can get that done. But this can be a problem. Knowing that I could do the work, how I would do it, and how long it would take me to do it causes me to have expectations. My expectations for myself are high, and I can be very critical of myself when I don't meet them. These high expectations become problematic when I pass the work off to others.
One of my favorite pieces of advice from Marcus Aurelius is to "be tolerant with others and strict with yourself." Holding others to the same standard you set for yourself is unfair. They didn't agree to that judgment from you. One of my favorite books on leadership, Leadership And Self-Deception, demonstrates how misguided and naive this judgment can be anyhow. It shows how easily you can narrow in on the weaknesses or failures of others while ignoring those same mistakes in yourself. It leads you to compare the times you were perfect to when they messed up. This results in a flawed picture of the other person, one with minimal basis in reality.
It is much more effective to recognize people's strengths and put them in a position to succeed. Of Marcus Aurelius, Cassius Dio wrote, "So long as a person did anything good, he would praise him and use him for the service in which he excelled, but to his other conduct he paid no attention." It would be best to find where they excel and put them in that position more often. The best path is to lean into their strengths. Asking someone to do a job they are not suited to is poor leadership. And if you don't need the work they are fit for done, don't put them in a position to fail and criticize them when they do. Find someone who excels in doing the work you need and let the other move on to somewhere that requires their unique skills.
When you are the leader, it is your job to guide people. Leading can be especially hard in a small company where it is always all hands on deck. You have a lot of responsibilities of your own to take care of. You are under a lot of pressure to complete your work. Everyone inside and outside the company is asking you for things. It is natural to feel overwhelmed. And then you are asked by someone you have hired to do a job how to do that job. At least it can feel that way. In that moment, it is easy to assume the worst of them. Are they not trying? Did they not think about it at all? Why do I always have to figure everything out for them?
This attitude is another lesson from Leadership And Self-Deception. You view other people as objects, as a two-dimensional version of them in your head, and not the living, breathing being they are. We all need help sometimes. The opportunity to talk through a complex problem with someone else is invaluable. Your needs are no more important than theirs. Because you're their leader, their needs are more important.
There is an excellent story about the Emperor Hadrian. While on an imperial tour, a woman blocked his path, asking for help. He attempted to move past her, responding, "I haven't got the time." She shouted back at him, "Well, stop being emperor then!" None of us are emperors by any stretch, but the sentiment is the same. As a leader, it is your job to lead and help the people you lead when they need it. You have to make time for that to be a successful leader.
I have a lot of work to do in this department. I have learned a lot of lessons so far, and I have many yet to uncover. Right now, I am focusing on being more lenient in my expectations of others and recognizing when they are doing a job that isn't right for them. I need to find someone who has been in my position to ask for advice. Learning from someone else's mistakes would be helpful rather than making them all myself.