Developing Our Character
“When leaders live out their deepest and most personal commitment to excellence, they bring out what is great in others as well.”
Peter Koestenbaum
Leadership development is broken.
To be sure, organizations spend countless hours buying books, hiring speakers, organizing retreats with the stated aim of “developing” the next generation of leaders.
But all of these initiatives share a fundamental flaw — focusing on developing the wrong things.
Most leadership programs revolve around skill-building—tactics, decision-making frameworks, performance management strategies.
The underlying assumption? That better techniques make better leaders.
But author Peter Koestenbaum offers a deeper insight: leadership isn’t just about competence (technical proficiency) — it’s about character—authenticity, attitude, and depth.
In other words, the real challenge of leadership isn’t what you do as much as how you show up when you do it.
Given this, it’s worth wondering — why do organizations show little interest or aptitude in developing high character leaders?
Simple. Companies train and develop what can be measured, scored, seen, gauged, and easily evaluated. Hard skills.
And what we’re left with is countless technically competent but uninspiring executives. Leaders who can optimize performance but cannot inspire trust.
The Competence Trap
When leaders struggle, their instinct is to double down on what they know—efficiency, strategy, problem-solving. They throw more tools at the problem instead of stepping back and assessing the bigger picture.
Example: A failing company hires an efficiency expert to cut costs instead of addressing the real issue—a lack of trust and vision at the top. The spreadsheets look better, but morale collapses.
Koestenbaum argues that true leadership requires wrestling with life’s more difficult questions:
Who am I as a leader?
What do I truly stand for?
Am I willing to take responsibility for the bigger picture?
But these questions are uncomfortable without the clarity of definitive answers. So however important it may be to wrestle with these foundational ideas, tactical solutions will always be easier to address. So, most leaders avoid the ambiguity of introspection and stick to what they can measure. We optimize for competence at the expense of building our character.
Shifting from a “Technical” to a “Philosophical” Approach
Koestenbaum argues that leaders should commit towards developing a leadership mind—one that embraces ambiguity, paradox, and self-awareness.
Instead of just learning new spreadsheet shortcuts, leaders must deepen their ability to think expansively and act with wisdom.
Koestenbaum believes true leadership requires balancing four key dimensions:
Vision – Seeing beyond immediate results to long-term impact.
Reality – Facing the world as it is, not as we wish it to be.
Ethics – Leading with principles, not just efficiency.
Courage – Making hard choices and owning responsibility.
Additionally, leaders need to ask hard questions:
Where am I avoiding discomfort in my leadership?
What fears are driving my decisions?
Am I leading in a way that reflects my deepest values?
This isn’t “soft” leadership work. It’s the kind of self-awareness that allows leaders to make clear, high-stakes decisions without being clouded by ego or insecurity.
Koestenbaum’s insight is deceptively simple: Leadership isn’t about knowing more. It’s about being more.
You don’t become a great leader by accumulating another skill. You become a great leader by having the courage to develop your character.
Because in the end, people don’t follow leaders because of their technical expertise. They follow them because of who they are.
Good luck out there.
Patrick
PS - Much of this blog pulled from Koestenbaum’s 2000 interview with Fast Company “Do You Have The Will to Lead?”