Discovery Conversation

When Your Strength Becomes Your Weakness

Jul 28, 2026

 

The salesperson whose confidence has tipped into arrogance. The leader who reacts to negative feedback with contempt. The one who treats every disagreement as a personal attack. The leader who always has to be the center of attention. The one who believes the rules don’t apply to them. The leader whose confidence intimidates the room. The leader who forgets their employees are human beings. The one whose office is full of people who learned a long time ago not to speak up.

I’ve watched these leadership styles for forty years. They are familiar to anyone who’s worked with one of these leaders. The cultural conversation around narcissism has gotten loud enough that there’s no shortage of voices ready to diagnose. That’s not my work. The pattern is what I’m interested in, not the diagnosis. And the pattern matters more than any one person who fits it.

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Here’s the coaching concept that names what’s actually happening. Strengths overused become weaknesses. It’s not a new idea. Marshall Goldsmith built a career on it. The Hogan assessment maps it as derailers. Any executive coach worth their fee has watched it play out over and over again. But naming a thing isn’t the same as recognizing it in yourself.

The trait that helped someone achieve a high leadership position or start a company can become a detriment if overused. Because the trait can be beneficial, it often gets missed as the culprit when problems arise.

The decisive leader who built the business by making fast calls eventually becomes the reckless one who moves without a full plan. The confident leader who carried the team through hard quarters becomes the arrogant one who remains certain even though the conditions have changed. The visionary who could see a bigger and brighter future is the leader whose view has narrowed into tunnel vision. High standards harden into perfectionism that breaks the people trying to deliver them. Charisma curdles into a cult of personality where no one says no.

Same strength. Different setting. The first is what got the leader to the top. The second is what eventually takes them out.

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This pattern shows up at the top more than it shows up anywhere else, and the reason is wired into the conditions. The traits we screen for in senior hiring — confidence, decisiveness, comfort with attention, willingness to dominate the room, tolerance for risk, likeability, the grit to move past criticism — are the same traits that, in excess, produce the failure modes. We don’t accidentally promote leaders who lean toward these traits. We select for them. So these traits cluster at the top.

This spotlights the complexity of leadership. It’s not that people are all good or all bad. Many of these individuals are highly effective, until — through a blindspot or an abuse of power — they overuse the gifts they have.

Research confirms what I see in practice. People who score high on narcissistic traits advance to CEO roles roughly twenty-nine percent faster than those who don’t. Whether or not they meet the clinical threshold for a diagnosis is a question for somebody else. The pattern of behavior is the part I’m interested in.

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In a recent session, I asked a client to name a leader in our present time that they admired. A simple question that produced a complex answer. With each name mentioned, the discussion included remarks about what the person does well, along with the criticism that is swirling around that person at the moment. Our leadership examples are complex right now. The inner workings of companies spread quickly now — Reddit threads, Glassdoor reviews, conversations that used to stay inside a building. What was once insider information is now widely known. Who would you name?

Details abstracted. The pattern is real; the person is not identifiable.

Run the pattern through some of the most celebrated leaders of the last forty years. Each one was held up for a strength that was real. Each one was eventually criticized for the same strength taken too far.

Jack Welch ran GE from 1981 to 2001 and grew its profits by four thousand percent. Fortune named him Manager of the Century. The same decisive performance focus that produced those numbers also produced rank-and-yank, a culture of fear, and a generation of protégés — Bob Nardelli at Home Depot and then Chrysler, James McNerney at 3M and then Boeing, Larry Johnston at Albertson’s — each one following the same arc. Real early results. Then overuse of the tools that produced them. David Gelles eventually wrote a book about him called The Man Who Broke Capitalism. Strength: performance discipline. Weakness: the same discipline applied without humanity.

Steve Jobs brought Apple back from near-collapse and built it into the most valuable company in the world. His perfectionist vision is what made the products. The same perfectionism produced extensively documented patterns of public humiliation, screaming at employees, and a culture of fear inside Apple while those products were being built. Strength: uncompromising taste in the work. Weakness: the same uncompromising posture applied to the people doing the work.

Jeff Bezos turned a bookstore into the dominant infrastructure of modern retail. The disruption reached markets everywhere. His executional intensity and customer obsession became the standard for what disciplined founder-leaders look like. The same intensity produced a workplace culture that the New York Times and dozens of other publications have documented as one that systematically breaks people. Strength: executional rigor. Weakness: the same rigor applied to human beings who struggle to live inside it.

Bob Iger acquired Pixar, Marvel, and Lucasfilm during his first run at Disney. He published a celebrated leadership book in 2019 that positioned him as the model of taste-driven, principled leadership. He handed off to Bob Chapek in 2020. Within two years, the Disney board brought him back to fix what had broken. Strength: visionary taste. Weakness: a leadership posture so concentrated in one person that the next generation couldn’t carry it.

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The case that has been studied most carefully is Travis Kalanick at Uber. The strength was real and consequential. He took an idea and built it into a global network in seven years. The growth was not luck. It came from a kind of competitive drive most leaders don’t have access to.

The same drive produced what is now one of the most-cited examples in management literature of how a toxic culture takes hold. Susan Fowler’s 2017 blog post laid out the harassment patterns. The internal investigation that followed forced the board to remove him. Charles O’Reilly at Stanford has studied this case for a point I keep coming back to in my own work — once a toxic culture takes hold, removing the leader doesn’t always remove the culture. The damage outlasts the founder. Once you create these cultures, it’s very hard to change them. There are long-term consequences.

Dara Khosrowshahi has been running Uber since 2017. He inherited a company that grew because of Kalanick’s strength and broke because of the same strength. That’s the pattern in its sharpest form. The trait that built the empire was the trait that hollowed it out.

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Here are a few indications I trust most.

If your team can’t function when you’re not in the room, your strength has already tipped. If your organization needs you back two years after you left, you didn’t build the leadership underneath you. Iger’s first run at Disney is one version of this test running into difficulty. The reality is more complex than a clean failure. Iger picked Chapek when the two were close, the relationship strained over time, the board brought Iger back, and now the succession process looks different with outside advisors helping shape the current transition. Iger has stepped into an advisory role. Other internal leaders have been elevated to balance the efforts of the new CEO. The honest reading is that succession is rarely clean. But the question worth sitting with is whether the strengths that made Iger’s first tenure work also crowded out the development of leaders who would be called to the work next.

I don’t know the answer. But the question is the test. The succession test is the strongest single indicator I’ve watched in forty years of coaching senior leaders and founders who sell their companies or pass the baton. The leader whose strength is still in proportion can step out of the room and the work continues. The leader whose strength has tipped into weakness can’t.

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Brené Brown spent several years studying senior leaders before she wrote her best seller, Dare to Lead. The frame she ended up with is the one I go back to when I work with people striving to become a better leader. So much so that I’ve gifted this book countless times. (I was building my own book club community with each one sent.)

Brené calls it the difference between armored leadership and daring leadership. Armor is the strength locked into its defensive setting — the decisive leader who has stopped listening, the confident leader who has closed off, the visionary who can’t hear another voice. Daring is the integrated version — strength held alongside vulnerability, decisiveness held alongside listening, vision held alongside doubt. 

Brown and Adam Grant took a deep dive into this argument this month on their podcast, Curiosity Shop. (I’ve quickly become a fan — worth checking out.) Strength and kindness are not opposites. Treating them as a tradeoff is the mistake that produces the pattern this piece has been describing. The leader whose strengths don’t tip into weaknesses is the one who learned, at some point along the way, to hold them in deliberate proportion.

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This isn’t a piece about narcissistic leaders. It’s a piece about how strengths work.

Every leader I’ve ever coached has at least one strength that has the potential to tip. The ones who do the work watch for it. The ones who don’t watch for it find out the hard way.

Leadership isn’t a fixed type. It’s not who you are at any single moment. It’s who you become through accumulated choices — each meeting, each conversation, each decision, each email. Your leadership style is the running sum of those choices. Strengths used well, day after day, build the kind of leader people trust. The same strengths overused, day after day, build something else. Same gifts. Different proportion. The difference shows up over time, not all at once.

Worth sitting with a question. Which of your strengths is becoming your weakness right now? The one that built your career. The one that got you to the room you’re in. The one you’d name first if I asked you to tell me what you’re good at. What does it look like when it’s tipped? Who in your life would tell you if it had?

Build something you can live inside. The architecture isn’t only the systems and the strategy and the team. It’s the daily work of keeping your strengths in proportion. The leader who can do that is the leader the next generation is actually asking for. Worth the work.

Ambition With Integrity™

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