What You Can Learn from My 5 Biggest Leadership Mistakes
I’ve had the privilege of leading teams of 12, 50, and 160 people in the last ten years. Throughout these leadership roles, I’ve made my share of mistakes that have taught me lessons I won’t forget.
My hope is that the lessons below enable you to avoid stepping in the same holes I did.
Mistake #1 — Bobby Makes a Unilateral Decision
The first lesson comes from my college days. After a fierce campaign and some cringeworthy campaign slogans like “With great Powers (my last name) comes great responsibility,” I became student body president of my alma mater, The College of Idaho.
Shortly after starting in my new role, I found a way to piss off the ski and snowboard team, basketball team, swimming team, and several other student contingencies in one fell swoop.
At the time, the college had two long semesters with a short, six-week “winter term” sandwiched in between. Partway through the year, an academic higher power made an arcane change to the college accreditation guidelines that put my school in jeopardy of losing accreditation if we didn’t make a speedy change to our trimester schedule.
After meeting for several weeks with the college’s board of trustees, faculty, staff, and administration, we came to the realization that the college would need to shorten its winter term from six weeks to four weeks in order to maintain accreditation.
By this time, I had survived hours of nuanced discussions about the ins and outs of the new academic guidelines, and I was fully convinced that we needed to make this winter term change. All that was left was for me to discuss the matter with the college’s student senate and draft a student resolution supporting the proposed semester adjustment.
I drafted the resolution and shared it at the next senate meeting. The general tone of my pitch could have been described as, “We have no decision but to make a change. Please support this.” I probably spent less than five minutes explaining the reasons behind the change and flippantly assumed everyone would be on board.
They weren’t.
Several senate members voiced that the semester change would impact our sports teams’ schedules. The timing of our “winter break” after the conclusion of winter term would now conflict with several sports team tournaments, which meant student athletes couldn’t go home to their families during the break. Same issue with various clubs: their big event of the winter season would now be in conflict with our break schedule.
A litany of unforeseen conflicts shattered my blissful ignorance that this would be an easy scheduling change. I had brazenly assumed that the schedule change would have little to no impact upon the student populous, but I could not have been more wrong.
Within minutes, I became Public Enemy #1 at The College of Idaho.
It sucked.
However, I learned a valuable lesson. Looking back on the prior month of discussions about the term schedule, I realized I should have involved the student body in the discussion weeks prior. I should have come to the student body with an articulate description of the problem that we collectively had to solve rather than coming to them with a dictate to be rubber-stamped.
No one likes to be told what to do. No one likes to be told there is only one option for how to move forward. No one likes to be a bystander while the decisions are made behind closed doors.
Lesson #1: Loop in your team early. Ask for their help and ideas. Whenever possible, don’t make decisions on behalf of others without their buy-in. Ask people how a change will impact them rather than making assumptions. Even if you know an unpleasant change needs to be made, explain the full situation to everyone involved. Explain the WHY and let others develop the solution with you.
“Leadership, it turns out, is not about being in charge. Leadership is about taking care of those in your charge.” -Simon Sinek
Mistake #2 — Bobby Clips His Team’s Wings
I completed my MBA in 2011, then accepted an assistant store manager position at Target, running a 50-person logistics team.
After soaking up all the knowledge I could in my first few months, I finally felt like I had my feet under me. My confidence buoyed, I began to tell others what to do. Sadly, my instructions often took the form of micromanagement.
I told my one of my team leads how she should run her backroom process. I made decisions about the truck unload process when another team lead was out of the office. I told people how to do things rather than trusting them.
Thankfully, the backroom team lead Karen eventually gave me feedback that I had overstepped. She explained the various things I had recently done that made her feel micromanaged.
During this conversation, I experienced a wave of emotions: surprise that I didn’t recognize myself making these mistakes, frustration at myself for not trusting the team, and thankfulness to Karen for having the courage to call me out. It was a valuable lesson to learn which has followed me throughout my life.
Lesson #2: True leadership is not telling others what to do. Leadership is supporting your team and occasionally giving them enough room to fail. Leadership is trusting that oftentimes others know better than you. Leadership is telling people WHAT needs to be accomplished without telling them HOW. Leadership is giving your team the latitude to amaze you with their ingenuity.
“Don’t tell people how to do things. Tell them what to do and let them surprise you with their results.” -General George Patton
Mistake #3 — Bobby Sugarcoats Feedback
In my first couple months in my assistant store manager role, I had the unpleasant task of firing a tenured team lead whose performance was not meeting expectations.
I had numerous conversations with the employee to share my concerns about his performance. But when the fateful day came to let him go, he was surprised, angry, and resentful.
Looking back, most of this was on me. Although I had been sharing feedback with him, I often sugarcoated it. I hemmed and hawed. I made things sound better than they really were. I sandwiched tough feedback between compliments and niceties.
In short, I didn’t do a good enough job of ramping up my feedback as the situation became more dire.
Termination shouldn’t be a surprise. Sure, some people will continue to deny that they are struggling in their role, but as a leader, my job is to make the state of affairs crystal clear before we get to that final conversation.
Lesson #3: Problems don’t get better on their own, and feedback doesn’t magically become easier to give the longer you wait. Be firm and direct when sharing tough feedback. Avoid surprises. Explain what is on the line. Don’t sugarcoat.
“One of the most important insights anyone in business can have is that it’s not cruel to tell people the truth respectfully and honestly.” -Patty McCord
*Click here to see my full article on giving feedback.
Mistake #4: Bobby Rolls Shit Downhill
Later in my career, I had a boss whose personality and style significantly differed from mine. She emphasized metrics over almost anything else, exhibiting a “Just get it done, I don’t care how” management style. I admired her spunk, but disagreed with her approach.
As a leader, I also value metrics; objective measurement is mandatory if you want to track progress. However, my leadership style definitely skews toward people over profit, meaning over metrics, and reasonability over rigidity.
Numerous times while I worked for that boss, I noticed myself taking on the persona of my boss when team members asked me questions.
When my team received an extra truck to unload in a given week or they weren’t sure how to complete their work in the allotted time, they came to me to ask for my guidance. Rather than staying true to my leadership style by putting people first and working together to find a solution, I found myself parroting back the “Just get it done” message on several occasions.
Every time afterwards, I had a hole in the pit of my stomach. I knew I had taken the easy way out — demanding the team hit the metrics without working together with them to do so. It was the moral equivalent of Pharaoh forcing the Egyptians to make bricks without straw.
Once I realized I had been doing this, I remembered the old phrase “shit rolls downhill.” If you’re unfamiliar, here’s an apt definition from Urban Dictionary: “In military parlance it means anything crappy coming from the top of the chain of command will hit everyone down to the bottom. This includes dumbass decision making, disciplinary actions, or simply a superior taking his frustrations out on subordinates.”
I had compromised my leadership style and values by mimicking the behavior I disliked in my boss. I eventually realized the error of my ways, although it was probably too late to salvage my relationships with a few team members.
Lesson #4: Shit really does roll downhill. You are responsible for stopping it. As a leader, part of your job is to absorb the stress from above and reflect confidence and determination to your team. Relentlessly push to exceed your company’s metrics, but don’t compromise your own values in order to do so.
“As a leader you are expected to be able to deal with an overwhelming workload and not be overwhelmed. That’s the job.” -Patty Azzarello
Mistake #5 — Bobby Loses a Massive Client
A couple years ago, I was appointed as the client services director for a multinational SaaS company. The company handled investment reporting for over $2.2 trillion in client assets, and I was responsible for ensuring we provided exceptional service to those clients.
Nine months into my new role, we lost a large client. It was a client I hadn’t personally spent much time with, but I had made several department changes that indirectly impacted that client and pulled resources away from the team who supported them.
When I received word that this client had decided to leave, my mind whiplashed through several feelings.
I was shocked. How did this happen?
Then I was sad. We let this client down. We dropped the ball. We promised “world-class service,” but we didn’t provide it.
Then I was scared. Losing a client like this was a big knock on me and my leadership of the department.
Then I was frustrated. Why did this situation come as a surprise to me? Why didn’t someone tell me things had gotten this bad?
Our brains are adept at crafting narratives that paint us as the “good guy.” We cling to stories that exonerate us of wrongdoing. For that reason, I clung to my feeling of frustration: someone should have told me that this client was having so many difficulties.
Then I stepped back. It was my responsibility to know about this. I should have asked better questions when I moved employees off the client’s support team. I should have instituted better mechanisms for tracking “at risk” clients. I should have seen the warning signals when we made prior mistakes with this client.
One of the demands of leadership is owning your mistakes and taking responsibility for what happens on your watch. This issue was on me.
Lesson #5: As a leader, you are ultimately responsible. Whenever an issue arises, retrospect on what you personally could have done to prevent the problem. Own it.
“When you are a leader, most things that go wrong are not directly your fault, but they are always your responsibility.” -Elena Botelho and Kim Powell
Thanks for sharing so candidly! I know this will help others.