Five Lessons from the Long Game
Last month, I attended the Forbes Iconoclast Summit, where I had the opportunity to hear from leaders, investors, founders, cultural icons, and athletes whose careers have shaped industries and expanded possibility.
One of the conversations that stayed with me was with Derek Jeter.
There are many reasons to admire Jeter’s career: the discipline, the championships, the consistency, the leadership, the pressure of performing at the highest level, and the rare ability to become both a sports icon and a respected business leader.
But what stayed with me most was not simply the story of winning. It was what he revealed about intentional leadership.
1. Even Greatness Can Feel Out of Place
One of the moments that stood out to me was Jeter reflecting on being at the World Economic Forum. Here was Derek Jeter, one of the most accomplished athletes of his generation, describing a moment where he felt out of place in a room filled with global leaders, executives, and people shaping business and policy at the highest levels.
That stayed with me.
Because it is easy to assume that once someone reaches a certain level of success, they no longer experience discomfort in rooms of power. But access does not always erase uncertainty. Achievement does not always eliminate the question, “Do I belong here?”
Many leaders know that feeling.
Walking into a room where the language is different, the networks are already formed,
the assumptions are unspoken, and where people seem to know the rules before you have even found your seat.
That kind of discomfort does not necessarily mean you do not belong. Sometimes it means you are entering a room that is stretching your sense of identity, influence, and possibility.
And that is part of leadership too.
Leadership often requires entering rooms before they feel familiar. It requires learning the language, building relationships, asking better questions, and allowing yourself to grow into spaces that once felt intimidating.
Jeter’s reflection reminded me that belonging is not always immediate. Sometimes it is built through presence, humility, curiosity, and the willingness to remain in the room long enough to learn from it.
2. Know the Person, Not Just the Performance
When Jeter talked about leadership, he did not begin with ego, status, or command. He talked about people.
His lesson was simple: Get to know your people.
Everyone needs something different to perform at their best. Some people need encouragement. Some need challenge. Some need space. Some need accountability. Some need confidence. Some need clarity. Some need to feel seen before they can fully contribute.
That sounds simple. But it is not always how organizations lead.
Too often, leaders manage roles instead of people. They evaluate performance without understanding context. They expect consistency without cultivating trust. They apply the same leadership approach to everyone and then wonder why some people disengage, underperform, or never fully step into their potential.
Intentional leadership requires more. It requires proximity, curiosity, and for leaders to ask:
Who is this person?
What do they need to do their best work?
What brings out their confidence?
What shuts them down?
What motivates them?
What causes them to hesitate?
What kind of environment allows them to contribute with both excellence and authenticity?
The best leaders do not simply demand performance. They create the conditions for it.
3. Failure Is Built Into the Game
Another leadership lesson from Jeter was his relationship with failure.
In baseball, failure is not an exception to the game. It is built into the game.
A .300 batting average is considered excellent. That means a batter does not get a hit 70 percent of the time.
Derek Jeter finished his career with a .310 batting average. So even one of the most accomplished players of his generation did not get a hit nearly 69 percent of the time.
And still, he built a Hall of Fame career.
That is what makes baseball such a powerful leadership metaphor. The game does not require perfection. It requires discipline, adjustment, recovery, confidence, and the willingness to step back into the batter’s box after missing.
That is a lesson many organizations need.
Too many workplace cultures claim to value innovation while punishing every misstep. They ask people to take risks but reward only perfection. They say they want creativity, candor, and experimentation, but create environments where people learn to protect themselves rather than stretch themselves.
A culture that cannot tolerate failure cannot produce sustained excellence.
It may produce compliance, carefulness, and performance theater, but it will not produce courage.
Jeter’s career is a reminder that excellence is not the absence of failure. Excellence is the ability to learn, adjust, return, and keep playing with discipline and belief.
For leaders, the question is not whether people will fail.
They will.
The better question is:
What does our culture teach people to do with failure?
Do they hide it?
Do they learn from it?
Do they become smaller because of it?
Do they receive support and correction?
Do they get another opportunity to step back into the box?
4. Be Careful What You Focus On
Jeter also offered a small but powerful lesson about attention. He used the example of golf: when you tell yourself, “Don’t hit it left,” the mind often locks onto the very thing you are trying to avoid.
That is true in leadership too.
When leaders are driven by fear, they often create the very conditions they are trying to prevent.
If the dominant messages are:
-“Don’t fail,” people become less innovative.
-“Don’t make us look bad,” people become less honest.
-“Don’t challenge leadership,” people become less courageous.
-“Don’t fall behind,” people become more anxious than focused.
Intentional leaders understand that attention shapes behavior.
People move toward what leaders consistently name, reward, measure, and model.
So the leadership question becomes:
Are we orienting people toward fear, or toward purpose?
Are we constantly naming what we want to avoid, or are we clear about what we are building?
5. Learn to Appreciate the Moment
One of Jeter’s reflections that felt deeply human was his admission that he did not always appreciate the moments as much as he wished he had. He was always looking ahead, always focused on what was next, always preparing for the next game, the next goal, the next achievement.
Many leaders understand that tension.
Ambition can be a gift. It can create discipline, drive, and extraordinary results. But unchecked ambition can also keep us from experiencing the meaning of what we have worked so hard to build.
There is a cost to always looking ahead.
We can achieve and not absorb. Win and not celebrate. Arrive and not notice. Lead and not feel the fullness of the journey.
Intentional leadership asks us to practice presence, not as a retreat from ambition, but as part of sustainable success.
Because if leaders never learn to appreciate the moment, they may teach everyone around them that nothing is ever enough.
The Leadership Reflection
What I carried away from Derek Jeter was not simply a sports lesson. It was a reminder that intentional leadership is built in the everyday practices that shape how people experience the rooms we lead.
These five lessons offer a useful reflection for any leader:
1. Belonging: What room is stretching me right now, and how am I allowing myself to grow into it?
2. People: Do I truly know what the people I lead need in order to do their best work?
3. Failure: What does my culture teach people to do when they miss, fall short, or make a mistake?
4. Focus: Am I orienting people toward what we fear, or toward what we are building?
5. Presence: Am I moving so quickly toward the next goal that I am missing the meaning of this moment?
The strongest cultures are not built by leaders who only know how to demand excellence.
They are built by leaders who know how to develop people, make room for learning, focus attention with intention, and remain present enough to recognize the growth happening along the way.
An Invitation to SHIFT
If your team is navigating change, pressure, or a season where excellence requires more than performance, I would welcome a conversation.
My work helps leaders and organizations create cultures where people feel seen, supported, challenged, and equipped to do their best work.
Let’s talk about what intentional leadership could look like in the rooms you lead.