How Leaders Learn: An Interview with Leadership Advisor Dan Holland

Although most of my articles on the Ken Kaufman Blog directly concern the state of healthcare, I am equally interested in the leadership qualities necessary in the contemporary socioeconomic environment—within hospitals and beyond.

To that end, I recently spoke, in depth, with a person I consider one of the finest minds in leadership.

Dan Holland has spent more than thirty years behind the scenes advising senior leaders at a wide variety of organizations, including TPG, Davita, Farallon Capital, The World Bank, Dell Technologies, Prologis, and Virgin Voyages.

A clinical psychologist by training, Dan has built his career coaching CEOs, founders, investors, and senior executives through consequential moments of leadership and life. Fiercely protective of client confidentiality, he has rarely spoken publicly about what he has learned from that work.

I met Dan in 2010 when he was introduced to me by Bain & Company. As an advisor to me and Kaufman Hall, I found Dan to be uniquely thoughtful in his analysis, direct in his approach, practical in his advice, and always far beyond the conventional wisdom about leadership.

I am grateful that Dan has agreed to allow me to share his insights with you.

Ken: How did you get into this line of work?

Dan: Pure luck. As a kid, I was fascinated by authority. As a teenager, I rebelled against it so thoroughly that I was sent to a therapist who literally saved my life and sparked a lifelong fascination with human nature.

I studied psychology in college, went on to earn a Ph.D. in Clinical Psychology, and along the way landed an internship at Wells Fargo Bank. That’s where I unexpectedly fell in love with the study of leadership.

Back in those days, the bank was led by a CEO straight out of central casting, Carl Reichardt. One day, I was sent to the executive floor to deliver a package. The elevator opened onto a serene, cathedral-like space. Thick, shag carpeting muffled every sound. Dark wood-paneled walls lined the floor. Eight executive offices were spaced evenly around the perimeter.

Something immediately caught my attention: None of the offices had doors. A lone receptionist sat behind a desk the size of a small boat, surrounded by ringing phones. I handed her the package, and she thanked me.

My curiosity getting the better of me, I asked, “Why don’t any of the offices have doors?”

She smiled and said, “Mr. Reichardt came in one day and found all the doors closed.” She paused. “So, he had them removed.”

I stood there for a moment, absorbing the answer.

I don’t remember much else about that day. But I remember thinking: That’s interesting.

I’ve been asking questions about leaders ever since.

After thirty years of listening to business leaders and the people they lead, what has surprised you most?

What has surprised me most is that the best leaders aren’t fundamentally different from everyone else. They have the same insecurities, blind spots, fears, ambitions, and capacity for self-deception as we all do.

What is different is their relationship with those things. The very best leaders I have met are confident enough to doubt themselves. Not their worth, capability, or every decision, but rather the completeness of their perspective.

They remain suspicious of their own certainty. They actively seek out people who disagree with them. They worry about what they might be missing. They are relentless in their pursuit of truth.

The very best leaders I have known never stop doubting themselves just enough to keep learning.

Can you give me an example?

One of the most confident and successful CEOs I have known subjected himself to feedback every year of his 20-year tenure. I collected it for 12 of those years and delivered the results to both him and his board.

Every year he would sort the feedback into three categories: Things he agreed with, things he wanted to explore further, and things he rejected.

Then he would test his thinking with me and with his board. Not because he lacked confidence. Because he respected the possibility that he might be wrong.

His mantra was simple, and he repeated it often with his executive team: “You have to respect the challenge.”

You’ve spent much of your career helping leaders hear and absorb difficult truths. What have you learned about the relationship between success and truth?

Success and truth have a complicated relationship. Success often makes truth harder to hear precisely when it becomes most necessary.

I can’t tell you how many successful leaders I’ve met who have inadvertently built force fields around themselves that invisibly repel unpleasantries. The forcefield isn’t malicious. In fact, most leaders don’t even know it’s there. But it doesn’t discriminate between noise and essential truths leaders need to hear.

People become more deferential. Bad news gets softened. Disagreement becomes riskier. And over time, leaders gain the ability to outsource many of life’s unpleasant realities. They can hire people to manage conflict, solve problems, clean up messes, and insulate them from consequences.

Every layer of insulation creates more distance between the leader and reality.

This sounds paradoxical. What is it about success that can make truth harder to hear?

Success changes us and the environment around us. It changes the whole weather system. Over the decades I’ve spent interviewing leaders and the people they lead, I’ve observed three things about this topic.

First, success subtly breeds contempt for dissent. Not because successful people are bad people, but because success itself is seductive and reinforcing. The more often your judgment is rewarded, the easier it becomes to trust it unquestioningly.

Second, nobody tells the whole truth. People filter. They edit. They protect. They spin. Sometimes to advance an agenda. Sometimes to avoid conflict. Sometimes to preserve a relationship. Sometimes because they’re afraid.

Third, success creates distance from consequences. The higher people rise, the less likely they are to experience the immediate impact of their decisions, and the more likely they are to receive information that has been filtered by others.

The result is a dangerous paradox. The more successful a leader becomes, the more dependent they are on other people to tell them the truth, precisely as that truth becomes harder to obtain.

You mention character. In a world that celebrates performance and results, does character really matter?

I don’t think character matters just because it’s virtuous. I think character matters because it determines whether a leader can hear difficult truths, tolerate dissent, admit mistakes, and change their mind when the evidence requires it.

I’ve met brilliant leaders who stopped growing because they couldn’t do those things. And I’ve met less gifted leaders who kept growing because they could.

It’s one thing for leaders to avail themselves of honest feedback. What they do with feedback is another. Some are injured and offended by tough feedback, others are curious, while others embrace it and figure out what to do with it.

To me, character is made up of curiosity, honesty, humility, and mature confidence. It matters because it determines whether success deepens and enriches wisdom or calcifies certainty.

Aside from delivering honest feedback, what else do you do with leaders you coach and advise?

I’ll answer with a story. I was at a dinner party years ago, one of those events where you’re not allowed to sit next to your partner or anyone you know. I was seated next to a man who looked as uncomfortable as I felt.

We made polite conversation while I scanned the table for people having more fun than I was so I could draw pity. Finding none, I gave up.

“So, what do you do?” I asked between bites of Caesar salad.

“I’m the pitching coach for the Mets,” he replied, as casually as if he worked at the corner store.

Immediately embarrassed by my initial lack of curiosity, I sat up straighter. I was instantly interested.

“What exactly does a pitching coach do?”

I imagined mechanics, drills, strategy, and the transmission of ancient baseball wisdom.

He shrugged. “I keep their head in the game.”

“Huh?”

“These kids have too much money, too much fame, too much of everything. Their personal lives are a trainwreck. I keep them focused on what matters.”

I’ve thought about that conversation often. When I really think about what I’ve done for the last thirty years, it’s remarkably similar.

I help leaders keep their heads in the game. I help them stay focused on what matters. I help them hear truths they might otherwise dismiss. And when the moment is right, I remind them who they’re trying to become.

Have you ever misread a leader and revised your thinking?

I have. Years ago, a CEO invited me to attend his executive leadership team meeting and provide him feedback. His ELT was made up of all men.

That evening, during a group dinner, I overheard the CEO make a joke about the physical appearance of a senior woman in the company. Several of the men around him laughed in agreement.

My internal reaction was swift. I didn’t like what I heard and felt it showed something profoundly true about the CEO. My respect for him evaporated. I decided I didn’t want to work with him, which paradoxically enabled me to do what I needed to do.

The next morning, I sent him an email. I told him what I had heard and reminded him he had made public statements about the need for more women on his ELT and the board.

Part of me hoped he would say thanks for the feedback, I’ll call you if I need anything in the future. What he did surprised me.

He forwarded my email to his entire executive team and told them, “I regret this, and I apologize.”

I had judged him quickly. He responded with more humility than I expected. Within a year, he had added three women to his leadership team, and two had joined his board.

What kind of leader still challenges your objectivity?

Funny enough, I am less dazzled by fabulous wealth and celebrity than I am by charisma, intelligence, and a sense of humor.

Who doesn’t love a charismatic leader? They’re fun. They’re magnetic. When they’re shining on you, it feels like standing in the warmth of the sun. They radiate confidence, optimism, and possibility.

And if they are funny, smart, and charismatic? That’s a trifecta for me.

And despite spending decades studying leaders and followers, despite knowing full well that charisma and humor do not necessarily translate into effective leadership, I still find myself drawn in.

At first. Then I do what I’ve always done. I ask questions. I interview people. I collect data. I observe and listen.

And eventually, the truth emerges. It always does if I pay attention.

You seem very loyal to the clients you serve. What have you learned about leadership and loyalty?

I once told the CEO of a very large global company that a member of his leadership team was actively undermining the high-performance culture he was trying to build.

His response was immediate: “I love all my children equally.”

It was such a human answer. He had hired every individual on his leadership team. He trusted them, invested in them, and had given them all extraordinary responsibility.

The problem was that the rest of the executive team experienced the individual as dishonest, manipulative, and divisive. Worst of all, the individual regularly invoked the CEO’s name to force his own agenda rather than the team’s.

He was eventually fired, but not before significant damage had been done to the CEO’s credibility as an assessor of all dimensions of executive team member performance, objective and subjective.

CEOs constantly receive competing and inconsistent feedback on the people they have selected for their leadership team, especially on subjective topics like honesty and collaboration. They know how to measure results, but loyalty can cloud their ability to see and confront destructive behavior that isn’t directly visible to them.

What techniques have you developed for delivering tough feedback?

The one I like best is also the hardest for me to do because it always feels risky: use myself.

I recently worked with a CEO who fit my trifecta of attraction: funny, charismatic, and smarter than everyone in every room he entered. That was also his Achilles heel. Half his leadership team hated working for him because every conversation eventually became a debate he needed to win.

Over months of working with him, I noticed a pattern in our interactions. No matter what I challenged, suggested, pointed out, or asked, he always had a rebuttal, an excuse, a reason why something would not work, that he had already thought of the question.

I grew increasingly frustrated working with him, and more importantly, realized he had no idea how to effectively leverage me: precisely what was preventing him from realizing his full potential as a leader.

So, I told him one day that as much as I enjoyed working with him, I found it impossible to have collaborative dialogue with him, that everything felt like a debate to be won or lost, that I was out of moves.

He sat quietly. He didn’t get mad, push back, or do his usual thing. Then he said the magic words: “You know, if you are feeling this way, I can only imagine how my team must feel. I obviously need to work on this.”

You clearly love your job. What’s your favorite part?

Hands down, after all these years, it is collecting and delivering feedback to leaders.

It’s like a treasure hunt. You have to earn the trust of the person you’re interviewing and ask just the right questions, which you can never know in advance. You’re not checking boxes on an interview guide. You’re talking to another human being about someone who is one of the most important figures in their life.

Every interview has a moment when you hit a vein of gold. Something honest. Something surprising. Something that can actually change the trajectory of how a leader leads.

Once you find the gold, the job is to make something of it – to shape it into a narrative so clear, so honest, and so compelling that the leader can’t help but be moved by it.

The challenge is to tell the truth without leaving the person defensive or hopeless. To create enough psychological safety that they can look at themselves honestly and feel inspired to grow.

That’s the moment I’ve been chasing for more than thirty years.

You can learn more about Dan and his background at https://www.danholland.org

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Ken Kaufman is Managing Director and co-founder of Kaufman Hall.

Disclaimer: The views and opinions expressed in this newsletter are those of the author and do not necessarily reflect the views or positions of Kaufman, Hall & Associates, LLC, Vizient, Inc., or their affiliates.