Leadership Lessons From My Own Mistakes — And How You Can Avoid Making Them.
In this blog post, you will learn about three mistakes I made in my 20-year leadership career and how they’ve influenced my approach today. I’m a West Point graduate, Army combat veteran, and 4X entrepreneur. I’ve led teams of all sizes from winning championships as an NCAA Division I athlete, deploying and leading 100+ Soldiers in Iraq, and leading teams for the multiple companies I’ve created.
Leadership to me consists of three simple principles: Effectively communicate your vision and expectations, lead by example, and just simply care for people. I grew into embracing these principles as my own through various experiences on my journey, good and bad. This post is not just about the lessons I’ve learned; it’s also to share that nobody is perfect and some of the most important lessons unexpectedly come from mistakes that you will inevitably make.
Lesson #1: Communicate Consistently and Transparently
The people you are leading need to know where the team is headed and what is required to get there. As a leader, it is your job to get them to buy in with full dedication to accomplish the vision and it’s important you ensure they understand how they contribute in their role. Feedback loops are also important — in the military, we did monthly, quarterly, and annual reviews for every Soldier and I continue this with teams I lead today.
One of the mistakes I made as a young lieutenant was signing off on a poor annual review of someone on our team who was never formally counseled on her poor performance. She was not a direct report to me, but I was part of her leadership team so my signature was included even though I did not write the review. She was taken off guard and had no idea she was performing poorly because her direct supervisor did not give her any of this feedback. Perhaps the 23-year-old in me was intimidated since she was so much older and had significantly more experience in the Army so I just avoided her and left it to her direct supervisor. As a result, the bad review led her to retire and there was always a part of me that wondered if she would have turned it around if we would’ve formerly counseled her prior to completing her review.
Lesson learned? Looking back I wish I would have at least ensured there was proper documentation and that she was formally informed of her poor performance. Today, I take every step to be transparent with poor performers, and sometimes those conversations are hard, but they are absolutely necessary. Lack of trust and resentment starts to grow when this type of necessary feedback is missed. A lot of people will sometimes delay these conversations or avoid them completely because they don’t like feeling confrontational or are worried about what people will think of them. The reality is that leadership isn’t a popularity contest and I will tell you the longer you wait to confront the behavior the bigger the negative impacts it will have on your team.
Lesson #2: They Are Always Watching You
As a leader, your presence matters and your team is always paying attention to your actions. How would it make you feel if you were instructed by your boss that every single person on the team has to show up to an event by 9 AM, but the boss doesn’t stroll in until 10 AM and obviously just woke up? It sucks huh? There’s that resentment and negativity that could sneak in again.
My ah-ha moment with this lesson was when I was a 19-year-old at West Point. I played the number one line for our tennis team, but I was only a sophomore. We had a captain who was a senior so my mindset was that I just needed to play and my worries were only my own. I was still struggling (like everybody else) adjusting to life at West Point and found myself late to practice a few times. I was late to an early morning practice again where I found my team captain, Annie, and my coach were waiting for me — both arms crossed. Annie told me “You are only a sophomore but everyone looks up to you since you are the top player on this team. You need to step it up and can’t be late because they are paying attention. I need your help with this.” Now, we all looked up to Annie immensely so these words coming directly out of her mouth (instead of my coach’s)carried a lot of weight on me. From that moment on, I knew I had to get my shit together and grow up a bit to support her. Fast forward to my senior year, I found myself having similar conversations with younger classmen — the torch had been passed!
Lesson learned? Never underestimate how much people look to you as a leader — you must emulate the example of what they should follow. They need to feel like you are with them every step of the way and not just there to carry power, protect your ego, and bark orders. At the end of the day, leadership is service to others.
Lesson #3: Boundaries Are Important
The relationships you develop with your team may become some of the strongest bonds you will have in life. There is something truly special when several individuals grow in trust and respect to become one kick-ass cohesive unit. Some activities for team bonding may pass on to some personal aspects of life - like you begin to know and perhaps even become friends with them and their families. Dining together or participating in fun activities outside of the work environment may serve as great ways to strengthen the bond of your team. However, be mindful of how crossing into more personal relationships may impact your professional one.
Five years ago I was growing another company and we were in startup mode. We’d recruited some teammates from outside the state (one moved to Texas from another country) so to save some money for the company, I ended up hosting them at my house. What was originally thought to be a temporary arrangement (maybe a few weeks) became a year-long roommate situation — one of them flew in once a month and lived with my wife and me for a week or so at a time. At first, it was super fun — I truly enjoyed and respected these people and we had a lot of things in common. However, the boundary between work and personal started to disappear, which started to even take a toll on my marriage. Ultimately, the professional relationship came to an end in a very awkward way. It’s quite uncomfortable to tell someone you no longer want to work with them when they are scheduled to live with you for a few more days.
Lesson learned? Needless to say, my wife and I will not be opening our home to any more roommate situations with coworkers. My cofounder did this as well and we are all in full agreement with this policy. I’m lucky that despite the awkwardness we still maintained good relations with those coworkers that stayed with us — we wouldn’t hesitate to hang out again if we were in the same city. You have to be mindful and ask yourself — “in the case that shit goes wrong in any part of my relationship with this person that works for me, am I going to prioritize the friendship or professional relationship?” You will ultimately have to choose one.
Becoming a good leader is a work in progress and doesn’t happen overnight. As with anything else, there are always going to be mistakes made and it’s important for leaders to learn from them in order to grow. Your team is always watching so you want to make sure they know where the lines are drawn between what’s acceptable behavior versus unacceptable behavior at work. It’s important to understand that you can always learn and getting better at anything requires time, effort, and humility.
