Mistakes of a Young Leader

There are few things better than sitting around, eating food and sharing crazy stories.

I was hanging with some friends over lunch a couple years ago and I heard a great story about a bad boss. Our friend worked on staff at an organization where the leader was just an absolute tyrant. People were afraid of him and he was known for verbally shaming people in public. Few, if any, people in the organization stood up to him.

One day, there was a theft in the building and some items were stolen. In the next meeting, he went on a tirade, talking about the lack of trust in their team. Finally one person stood up and called him out saying, “There are 3 people who have a key to that room – me, him (pointing to another staff member) and you. I didn’t take it, he said he didn’t take it. So that only leaves you!” I’m not sure who was more shocked the leader or the rest of the room, but the leader stood down and moved on to another subject.

That story reminded me of many leadership habits I hope to never embrace. In the moment, I thanked God for the great individuals I’ve worked for in recent years. But it also reminded me of how many mistakes I’ve made in my life as a leader. While I’m in the first half of my leadership life, I can already look back and identify some missteps along the way.

Mistakes of a Young Leader

I recently sat down and identified five mistakes I made as a young leader, which made an already difficult task even more challenging. If you’ve made these, I hope the following helps you dig the lesson out of the frustrating experience. If you haven’t made these, I hope you can learn from my missteps.

1. I underestimated the gap between my taste and my talent.

Ira Glass of NPR fame has this brilliant perspective on what happens in the life of a young artist and I think it applies to leadership as well. You can watch this typography video to get his whole perspective, but he challenges young creatives to embrace the gap between their taste and the quality of their work. He encourages us to do a huge volume of work, put ourselves on a deadline and keep showing up.

I’m a speaker and my first presentations were just terrible. I remember I once gave a talk where my handout covered the front and back of an 8.5×11 sheet of paper with size 12 font. The talk was 55 minutes long and I can’t even remember how many slides I had. I mean, it still pains me to think about it!

We often know what good is but we struggle in the beginning to be good ourselves.

2. I misunderstood the difference between getting things done and leading a team to get things done.

One of my greatest struggles as a young leader has been rejecting the lie that it is easier to just do it myself. Many leaders function as doers instead of catalysts, being very productive rather being very empowering. The old adage is true – if people aren’t following you, you aren’t leading; you’re just taking a walk. Productivity is not the goal as a leader; building a high-performing team is. I learned as a leader that my way of working was often the lid for the teams and projects I led.

3. I shortchanged myself by valuing short-term gains over long-term potential.

Our world is completely stuck in the present moment. We don’t plan ahead and we struggle to see today in the context of the past (see the current discussion of Steph Curry’s ability in the context of basketball history). As a result we end up valuing talent over character, shocking ourselves when the really gifted person is terrible to be around. We lead too stridently, sacrificing long-term success for the sake of some short-term wins. We become stuck in the moment and fail to lead the people we lead.

Instead, we must push back and counter-culturally practice patience, steadfast endurance, focus and sacrifice.

4. I missed out on opportunities to build relationships.

In his book, Do Over: Rescue Monday, Reinvent Your Work and Never Get Stuck, Jon Acuff helps readers build a Career Savings Account to navigate the crises moments in your career. One such crisis is what Jon calls a “Career Bump,” which comes when you get fired or laid off. In this moment, it is the power of our networks which will help is handle a career bounce.

The problem is when we prioritize getting ahead over making friends, we miss out on the opportunity to build a network before we need it. Whenever I speak on the subject of community, one of my favorite lines is “you don’t know how much you need people until you need people.” While many people will encourage a focus on building skills early on (see the Ira Glass comment above), it is also imperative to build our network of relationships – both deep and superficial.

5. I miscalculated how much I could learn from bad leaders.

If we can only learn from good examples, we’ll miss out on a lot of lessons. The truth is we can learn what to do and what not to do from a bad leader. Having served under plenty of good and bad leaders, I sometimes wonder if I didn’t learn more from the bad leaders than the good ones.

Being under a bad leader forces you to think what you would do differently. I’ve made several pacts with myself to not repeat a pattern I observed in someone else. The determining factor for learning under a bad leader is attitude. Being teachable and learning and growing are far more about your attitude and your posture than they are your environment and your supervisors.

In his book, The Lives of George and Robert Stephenson, Samuel Smiles wrote, “We learn wisdom from failure much more than from success. We discover what will do, by finding out what will not do; and probably he who never made a mistake never made a discovery.”

Mistakes, when mined for wisdom, can lead us to incredible discoveries!

What is one mistake you’ve made recently which taught you an invaluable lesson?