Entering the Arena: The Four Positions That Define Leadership Identity

Dec 9

When do you take the opportunity to step back and assess how you’re truly performing? I often find myself wrapped up in the navigation of “need to dos,” “have to dos,” and “want to dos,” just like anyone else. In that pace, it becomes easy to lose track of my own progress. I’ve said before that misplaced priorities can derail purpose-driven leadership, and that hardship alone is not always a badge of progress. With that in mind, I want to talk about the battles we face—personal and professional—and how they shape our leadership identity.

Every leader has a unique style, or at least they should. That style becomes the lens through which colleagues, subordinates, and administrators understand who we are as leaders. I believe there are four themes of leadership identity, and three of them have value depending on the situation.

I keep two quotes posted in my office. One reminds me that no event in my life has ever fully defeated me. The second is President Theodore Roosevelt’s “The Man in the Arena,” which I revisit often:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

This quote is the foundation for the leadership themes I use. The arena is a place of triumph and defeat, but more importantly, it is a place of accountability and transparency. In the arena, a leader stands exposed—owning both victory and failure. Every battle is different, and every challenge requires a different angle of approach. Within that arena, leaders can place themselves in three positions.

Leading From the Front

This theme positions the leader at the forefront of chaos. They are the first to act, the first to bear the weight of the challenge, and often the first to fall.

Pros: Leading from the front sets the tone. It communicates “follow me,” inspires through action, and models tenacity. This approach can ignite collective motivation.

Cons: A leader can become hyper-focused on a single task, losing sight of the bigger picture and leaving their team vulnerable. It may also inadvertently signal distrust by overshadowing the expertise of the team.

Leading Side-by-Side

Here, the leader is shoulder-to-shoulder with their team—fully in the trenches.

Pros: The message becomes “I’m with you.” This theme promotes equality and shared ownership. Decision-making becomes collaborative, and the team moves in unison.

Cons: The downside is the potential creation of a leadership vacuum. Without clear direction, dissenting opinions can fracture the group. What begins as unity can quickly become a cluster of individuals competing for identity rather than cohesion.

Leading From the Back

This position elevates the leader just enough to see the whole field. From here, they delegate, allocate resources, and ensure blind spots are covered.

Pros: The message becomes “I have your backs.” This theme empowers the team, allowing them to leverage their strengths while the leader oversees and supports.

Cons: When used poorly, this style can morph into unilateral decision-making or paralysis through insecurity. Communication can falter, and the team may interpret the leader’s distance as disconnection or indifference.

The Fourth Position: Skybox Leadership

Earlier, I said four themes exist—three with purpose, one without. Skybox Leadership has no rightful place in effective leadership.

Leading from the Skybox removes the leader from the arena entirely. Their vantage point is wide but detached. The work below becomes a spectacle—something to cheer or boo. Praise is given only in victory. Criticism is loud, reactionary, and delivered without context.

Skybox leaders become the “could have,” “should have,” and “would have” crowd—the ones who cast blame for failures and claim credit for victories they never touched. We’ve all encountered them. They can exist at any level of an organization, and their presence corrodes culture. Ego thrives. Humility disappears. The organization suffers.