Lessons in Failure

When I was an officer, I struggled deeply with failure. Not just the act of making mistakes, but the way a mistake would cause me to see myself as fundamentally flawed. Perfectionism had followed me my entire life, showing up in the way I approached my work, my goals, and my own self-worth. When I became a leader responsible for ten new officers, I assumed that drive for perfection would serve me well. Instead, it got worse.

I started projecting my perfectionism onto my team. Every small mistake felt like a reflection of my leadership, so I began hovering, correcting, and controlling. I told myself I was just holding the team to a high standard. In reality, I was creating an environment where people were more afraid of getting something wrong than they were motivated to get something right. The result was a team that avoided me rather than sought out my guidance.

I knew something had to change, but I could not figure out what. I was doing everything I thought a leader was supposed to do. I was present, I was engaged, and I cared deeply about the outcome. What I did not realize was that caring too much about the outcome, in the wrong way, was exactly the problem.

Around that time, I went bass fishing with my dad.  Between casts, I started telling him what was going on. I walked him through the mistakes my officers were making, the frustration I was carrying, and the growing feeling that I was failing as a leader despite all my effort. He listened without interrupting. When I finished, he looked at me and said something I was not expecting.

"You have to let them fail."

I pushed back immediately. My whole approach to leadership had been built around preventing failure, not allowing it. I told him that my job was to set my people up for success. How could stepping back and watching them make mistakes be a good thing? That felt like neglect of my duty.

He was patient with me. He explained that leadership is far more nuanced than simply making sure people do not make mistakes. He told me I needed to give people the space to work through problems on their own, to struggle a little, and to find solutions without me standing over their shoulder every step of the way.. He told me I needed to decide how I was defining failure in the first place. Did someone fail because they made a mistake? Or did they fail because they did not handle something exactly the way I would have?

Those two questions changed how I approached leadership.

I began to realize that I had been treating my own preferences and habits as the universal standard, and my team had been silently paying the price for it. When an officer handled a situation differently than I would have but still got a good result, I had been counting that as a problem. That was not fair to them, and it was not good leadership. I had confused familiarity with correctness.

I was also not allowing them to make mistakes and then learn from them.  Some of the best lessons I learned in my life came on the heels of a major failure. I wrote a blog about learning from mistakes that you can read here.   I was robbing my people of the opportunity to learn from their own mistakes.  This is a balance, because I needed to identify what mistakes could significantly impact someone’s career, versus those that would be good learning experiences. 

In the end, I learned that real leadership is not about producing copies of yourself. It is about giving people the room to grow, to make mistakes, to stumble, and to find their own footing in the process.

After that fishing trip, I made a conscious effort to step back. I started asking questions instead of giving answers. I let my officers work through problems and only stepped in when something truly required my involvement. The dynamic on my team shifted. People started coming to me again because they were learning to trust me.

If you lead people, I would encourage you to sit with those same two questions my dad asked me. How are you defining failure? And whose standard are you actually holding people to? The answers might be uncomfortable, but they might also change the way you lead for the rest of your career, just like they did for me.