The Secret Sauce of Superbosses

What looks solid and unassailable from a distance may actually be a lot more fragile than we like to think.

I had been a university professor for 10 years by the time I met Alan Elkins.  Alan was very different from most of my MBA students. He was a psychiatrist and knew how to ask better questions than I did. He was also 68 years old. Most students are in their twenties.

At the time I was in the midst of an intensive research project on CEO failure and had compiled dozens of case studies about leaders who failed at a company, such as Stephen Wiggins of Oxford Health Systems, George Fisher and Gary Tooker at Motorola, and William Smithburg of Quaker/Snapple. Perhaps unsurprisingly, Alan was interested in the project, and encouraged me to interview these leaders, and others, to find out what really caused these leaders and companies to go astray in such a spectacular fashion.

I couldn’t imagine why these CEOs – high-profile and already pilloried for their incompetence – would ever consider going on record discussing how they had screwed up. But Alan was persuasive, and offered to help in organizing and conducting the interviews.


Oh, the humanity

It turns out, if you want to really understand why companies do what they do, you have to pay attention to the leaders running those companies, and recognize that they are human too. It’s not an accident that the great strategy treatises of history, from Sun Tuz’s The Art of War to Shakespeare’s Richard III, take readers into the mind of the leader – their frailties as much as their power.

What was said by the executives Alan and I spoke to brought home to me a basic truth about CEOs – it turns out they’re no different than you and me. Rather than being unfeeling technocrats, they’re real people, with all the warts and biases and emotions that go along with that.

For example, have you ever messed-up something in a big way but when called-out on it, proceed to blame everyone else? That’s just how one CEO evaluated a corporate meltdown that cost him his job. In our interview, he proceeded to tell me that there were “seven reasons” why the company fell apart. First, my chief financial officer let me down; second, our customers were not smart enough to grasp what we were trying to do; third, the regulators were out to get me; and on and on. You get the picture.

For others, however, speaking to Alan and I was almost cathartic; an opportunity to talk freely about what went wrong.


The heart of the matter

Some of the most revealing insights in to how senior executives think emerged when I interviewed protégés of great leaders who had spawned a generation of talent in their industries, people who I call the superbosses.

Of course, it’s easy to fall into the trap of believing that the captains of industry are heartless, just in it for the money. And I’m not suggesting there aren’t people like that around. What I learned, however, is something quite different. Time and again senior executives and CEOs who had worked for a superboss talked about what their former boss had meant to them, personally. I heard about support, loyalty and emotional bonds.

When I interviewed Chase Coleman, billionaire hedge fund investor and protégé of superboss Julian Robertson (founder of Tiger Management and directly responsible for spawning dozens of successful investment companies), Coleman described how Robertson, with just a slight nod, could provide a powerful affirmation of Coleman’s work. He was attuned to the approval of his superboss, just like a son to a father.

This paternal or maternal relationship was reflected in other interviews I did. For example, Stevan Alburty, a manager at advertising agency Chiat/Day (famous for creating the Apple 1984 advertisement announcing the launch of the Macintosh), told me that his former boss Jay Chiat “had a bigger impact on my life and value system than my own parents did. He was an incredibly impacting person, and I consider myself fortunate to have worked with him”.

Jean-Pierre Moullé, a longtime Chez Panisse chef who was fired by superboss Alice Waters, put it this way: “Her employees will give and do anything for her. But sometimes they can be annoyed . . . like when your mother tells you over and over to clean up your room, clean up your room, clean up your room. And she’s right. So that’s it.”


Loyalty and regrets

I even heard about love and regret.

Several former managers under fashion impresario Ralph Lauren used that word, love, to describe their feelings toward their superboss. Sal Cesarani, an award-winning designer who worked for Ralph Lauren in the early years, put it this way: “If you were to talk to [any other former employees of Ralph Lauren], they would tell you the same thing: they would have given him their lives.”

Yet when it came time to leave, Cesarani remembers it as an excruciating decision: “Lauren never jumped up and down, but he would shake his head in disbelief that I would have betrayed him, because he always felt that I was there for him. And I really took enormous amounts of stress to decide what I wanted to do.” Even years later, the memory of leaving Lauren seemed to provoke sadness and regret in Cesarani; his voice hung heavily during our interview.

We put CEOs on such a high pedestal – especially now in places like Silicon Valley – but we sometimes forget that they’re human, and therefore, emotional. Many of the same vulnerabilities we have, they have too. Many of the same emotional bonds that govern our lives, they have too.

Alan Elkins is gone now, but his insight in to people – no matter how rich or famous – has stayed with me. So many people build these fabulous constructions about the leaders around them, and about themselves. What looks solid and unassailable from a distance may actually be a lot more fragile than we like to think.


Sydney Finkelstein is the Steven Roth Professor of Management, Director of the Leadership Center, and Director of the Tuck Executive Program at the Tuck School of Business at Dartmouth College. His new book is Superbosses: How Exceptional Leaders Manage the Flow of Talent (Portfolio/Penguin, 2016). An earlier version of this article appears on BBC Capital.