We’ve all had one — a boss who seemed hopelessly ineffective, a leader who inspired eyerolls rather than loyalty. And most of us, at some point, have quietly wondered: are they just… bad at this? Or is there actually hope?
It’s a question I’ve been asked many times. And while I always have an answer ready, it’s one of those questions that keeps nagging at me. Because it’s not really about the leader in question. It’s about how we think about leadership itself.
The Mythology We’re Up Against
Our culture mythologizes leadership. The names we reach for — Churchill, Gandhi, Lincoln, FDR, Martin Luther King — all seem to share the same impossible qualities: perfect judgment, iron will, unshakeable moral clarity. No wonder real leaders feel like they’re failing by comparison.
As I’ve written before, the idea of the perfect, all-knowing, endlessly strong leader is an illusion. Trying to perform that ideal is, paradoxically, one of the fastest paths to failure.
So when someone asks me whether a leader is “bad,” I find myself immediately rejecting the premise and reframing it.
It’s not about who a leader is. It’s about what a leader does.
On Character vs. Behavior
I want to spend a moment with the first half of that sentence. I don’t believe there is such a thing as a fundamentally bad person — one who is entirely without redemptive qualities. We all share common humanity. Each of us has the capacity for both generosity and harm, for wisdom and blind spots.
(I do make an exception for sociopaths, psychopaths, and others whose conditions genuinely prevent them from functioning with integrity in organizational life. They should not hold leadership positions. Full stop.)
But the vast majority of leaders who seem “bad” are not morally deficient. They are behaviorally misaligned and that is a very different problem, with very different solutions.
Leadership Is a Set of Behaviors — Not a Personality Type
In my coaching practice, I use the Enneagram extensively — a rich framework for understanding core motivations, fears, and internal dynamics. People often ask me: which Enneagram type makes the best leader? Or conversely, which types are disqualified?
The answer is: none and none. Any type can reach full potential and lead with genuine effectiveness. The Enneagram doesn’t rank people. It illuminates them.
Leadership skills, mindsets, and behaviors can be taught and learned by anyone willing to do the work. Which means the real question is never “is this person a bad leader?” It’s: “does this person have the desire and capacity to grow into the leader this role requires?”
That means asking: Is there real self-awareness? An openness to identify blind spots? A willingness to be vulnerable to ask questions before acting, to sit with uncertainty, to trust others enough to be challenged by them?
If the answer is yes, the path forward is open. If the answer is no — no coach, no colleague, no amount of feedback will move the needle.
When Ego Becomes the Mission
Sometimes it works in reverse. A leader who once had genuine strengths sees them slowly eroded — not by incompetence, but by ego.
This is one of the most common tragedies in organizational life, and anyone who has spent time in the nonprofit sector has witnessed it. A person arrives humble, mission-driven, effective. And then, gradually, the mission becomes secondary to their image of themselves as the person delivering it.
The tells are not subtle, once you know what to look for:
• They care more about their personal brand than the organizational mission.
• They position themselves as the primary or sole contributor to the work.
• Their circle of trusted advisors has shrunk to a small group of people who won’t challenge them.
• They’ve lost the capacity to genuinely care about the people doing the work alongside them.
• They cannot see or won’t look at their own blind spots.
Brené Brown, in Dare to Lead, describes ego as armor — a way of protecting a fragile self-image at the cost of authentic connection, honest self-assessment and accountability. A leader overtaken by ego can’t do the fundamental work of leadership: question their own worldview. And without that, no external intervention will help.
The One Question That Actually Matters
Here’s what I’ve come to believe, after years of working with and coaching leaders across sectors: the distinction between a leader who grows and one who stagnates is rarely about talent, intelligence, or even experience. It’s about orientation.
Do they have a growth mindset, or a fixed one? Are they defined by who they’ve decided they are, or by what they’re actively learning?
Many business school case studies and organizational behavior authors write about the power of intellectual humility. Leaders who define themselves by what they’re doing and learning, rather than by a fixed identity, are far more likely to keep developing. They hold their assumptions lightly. They stay genuinely curious about themselves.
That curiosity, more than any single skill or quality, is the foundation of good leadership. Leaders are not set in stone. You can teach an old dog new tricks. The best leaders are in a constant state of evaluation, evolution, and honest self-inquiry.
The leaders who grow aren’t the ones who have it all figured out. They’re the ones who stay genuinely curious about themselves. That’s the whole job.
