It’s that time once again, Loyal Leaders, for another rummaging expedition into the Leadership Toolbox! As always, I am Captain Fletch, your loyal host, and I am very excited about this month’s topic. This month, I would like to do some self-evaluation of what kind of leader we are within our organization. At the heart of the matter, are we simply seeking to climb the corporate ladder, or are we willing to accept lesser ambitions in favor of the team’s success?

What is Your Endgame?

It is no secret that most people have ambitions. For leaders, our ambitions are directly tied to how we operate and how our people perceive our actions. There is nothing wrong with having a goal to make it to the highest levels of leadership in an organization. In the early years of my leadership development, people often told me that I would be a general officer someday.

While it was a nice compliment, it was not my primary ambition to have stars pinned on my shoulders. On the contrary, I just wanted to be a leader with whom people respected and enjoyed working. Having witnessed my father come home from work on the railroad every day and listening to him air his grievances about bad leaders, I decided I wanted to be the kind of leader my dad would have enjoyed having around. I wanted to be a leader that was known for caring for the team first and foremost. That was my endgame. 

Admittedly, as a young man, I did not realize the compromise that often accompanies that endgame. The truth is that it is rare for a leader to both rise to the top and also be a revered team player. The reason is that rising to the top involves some degree of gamesmanship to get there. This is evident in the fact that general officers in the military are tied directly to congressional review and approval. 

Although all military officer promotions are approved by Congress, general officers are at a level beyond the normal review and approval process. This means that you have to have some level of connection with those who will review and approve your promotion. This is what many like to call “being a member of the club.” So, how do you maintain a membership in the club while also being a leader of the people? 

In my opinion, this is a rather new conundrum because if we look historically, some of the most notable leaders rose through the ranks because of their achievements rather than their connections. It would seem that this system developed when the mainstream ideology about operational control shifted from decentralization to centralization. In other words, when operational control was taken from the hands of those in the field and given to those in the office, it became more difficult to determine the quality of leaders deserving of promotion. This forced leaders to resort to making themselves visible to those who determine their fate. 

Which Path is Better?

The previous discussion leads to further questioning with respect to leadership as we must ask ourselves, can we make a greater difference by climbing the ladder or playing for the team? In a perfect world, the true answer is a balance of both, maintaining our humility and connection to the people as we rise through the ranks. This would enable us to make decisions with the full scope of their impact on the organization versus simply deciding in a vacuum of senior leadership. But, as I also highlighted previously, leaders who can navigate both paths are few and far between. 

I have worked for both types of leaders: those who rose through the ranks to satisfy their ambitions and those who were leaders of the people. In all my years of experience, I can count the number of leaders who could do both on one hand. In actuality, many organizations promote individuals by attrition as good leaders depart organizations that fail to change. Again, referring to the military, many senior leaders found themselves in higher ranks in the last 20 years because the better-quality personnel departed as they were burned out or jaded by an organization that refused to listen. In my experience in the civilian world, the puzzle is not really that different. 

I recognized that I could make the greatest impact on my teams by being the leader who cared more about the mission and the people than with my own personal successes and achievements. In other words, I refused to join the club…which cost me over the years. I watched many others receive accolades and promotions, some slightly senior to me, who received credit for work that I had done. I accepted the fact that I would never be able to navigate both paths. The reason is that I did not want to compromise who I am and what I meant to my people to partake in the gamesmanship. I would not be able to sleep at night if the people in the organization perceived me as a member of the club. 

What is the Right Answer?

I realize that this discussion can seem like a rant about an organizational problem revolving around political gamesmanship and how everyone should be a team player first. That is not my main goal in this conversation. Rather, I believe there are some people bound for senior leadership, some bound to lead where they are among the people, and a rare few who can do both. The truth is the right answer lies in the structure of our organizations. Let me ask you: does your organization do performance evaluations? If so, do leaders write performance evaluations for their personnel, or do they have them write their own to form the basis of the employee discussion? I ask these questions because it goes back to the concept of centralized control. How can we claim to be organizations that promote the most qualified and talented leaders in our teams if we lead from the office chair? 

This means that we as leaders have to make a dedicated effort to get out and see our people in action. As a company grade officer, I made it a point to spend as much time in the field as possible. This enabled me to see those troops who were leading and getting the job done with my own eyes. Many of my peers spent the majority of their time in the office, and our office work could easily be done in a minimal amount of time each week. Why? Because they were visible to the senior leadership in the office regularly. 

It seems that being in the field has become equated to not being an effective leader simply because you are not visible in the office. In reality, however, it should be the opposite. It is 2024, and a leader today can easily execute a large part of their administrative tasks from the cab of a truck. 

Parting Thoughts

People often ask me if I regret leaving the military. My response is always the same, “I miss my troops and the work, but I don’t miss the game.” As you already know, I never became General Fletcher, and that is okay! I do not regret my career decisions because I feel I made more of an impact as a Captain than some people do in their entire careers. Since leaving, I have continued to help former troops transition and find their way to meet their goals and ambitions. I see this as a greater honor than a medal or promotion, and I see that these people continually seek my input and support in their lives. I have always believed that captains were the coolest officers in the chain of command anyway, and I will forever be a captain in my heart. 

So, what kind of leader are you? Did you make a career climbing the ladder as high as possible? Are you stalled in place because you care most about the team? Or are you one of the few that has been able to do both? Understanding yourself in relation to this complex puzzle can definitely be a game changer to your organization and one of the most advanced tools in your box. Until next time, Captain Fletch over and out.

P.S. The Driller is starting a Spotify playlist called ‘Fletch’s Favorites.’ It will be an ongoing selection of songs I enjoy on the job site, and I will include a track title with each article! 

I think this one is fitting this month: “Things That Matter”  by Jameson Rodgers.