How a 'superboss' turns employees into bosses

Most of us just want a decent boss. Someone who doesn't take credit for our work. Who doesn't mind if we don't immediately respond to an email sent after 11 p.m. Who actually asks us once in a while how we're doing.

But Dartmouth business school professor Sydney Finkelstein decided to study what he calls “Superbosses” — leaders who not only get their people to achieve great things, but also go on to become great leaders themselves.

In the process, he examines the protégés and careers of leaders such as Bill Walsh, the former San Francisco 49ers coach who launched the careers of so many other National Football League coaches; fast-casual dining pioneer Norman Brinker, whose employees went on to found many similar restaurant joints; and fashion magnate Ralph Lauren, who helped along designers such as Joseph Abboud and Vera Wang.

But don't get the wrong idea, Finkelstein says: Superbosses are not necessarily nice, generous mentors. Rather, they tend to be motivated by their own goals, whether it's to win, improve their legacy, or better their own work or their own art. We spoke with Finkelstein about what we can learn from these “talent spawners.” This interview has been edited for length and clarity.

Q: How did you come up with the idea for the book?

A: I'm really into food. An article I read showed a graphic of a famous French chef — I wish I could remember who it was — which talked about all his sous-chefs and former sous-chefs. It graphed out this tree of how everybody went on after a period of time and worked at all these other really great restaurants, who used to work for this great chef.

I thought, ‘That's really kind of cool,' and I wondered whether that's true anywhere else, so I started to poke around. I wanted to know who's the best of the best, and that's what got me to [Chez Panisse chef and founder] Alice Waters. The evidence is pretty overwhelming — the number of chefs and bakers and restaurateurs who worked for her.

I'd also heard stories in the past about coach Bill Walsh and how a lot of former assistant coaches had become head coaches.

Q: How do you define this?

A: A superboss is a leader who helps other people accomplish more than they ever thought possible. They become incredibly capable and, as a result, become highly sought-after leaders in their own right.

That's the most counterintuitive part of what I found. The best people will want to move on to bigger and bigger responsibilities. It would be great if you were growing enough as an organization to keep all those people. But they want to run the show. They want to create a new business. They want to be the CEO. Why do we run organizations as if we have control over what people do for their entire careers?

If you know that the best people are going to go at some point, then why not create an organization that doesn't try to optimize on talent retention but optimize on talent flow?

Q: And superbosses think about this differently?

A: For example, Tommy Frist, who was the longtime CEO of Hospital Corporation of America, ended up spinning off and creating all these businesses. He was a very entrepreneurial guy, and he would create an opportunity with an individual in mind. That worked for him — he knew [the protégé] was ready to go on to something better, but he stayed in his orbit.

You see it in comedy, too. Lorne Michaels — he's now executive producer of the Jimmy Fallon show, the Seth Meyers show, he invested in Tina Fey for “30 Rock.” You're going to lose some of those people. But you want to lose them because it makes room for other great people.

Q: Many General Electric executives under Jack Welch went on to lead companies elsewhere. Was Jack Welch a superboss?

A: No, I would not list him as one. GE and PepsiCo and some of these companies we used to call “academy companies,” they bore me quite a bit. GE has had very mixed results from a lot of people who came out of the Jack Welch era. I was more curious about the individuals and not the company. That's what makes it so much more teachable. If you read about GE or McKinsey as an individual, how are you going to re-create that yourself?

Q: Superbosses, as you define them, are not all these nice, generous types. How do you categorize them?

A: A lot of people throw around the word “mentor,” but it's such a common word now that it doesn't have a ton of meaning. What superbosses do is just on a different scale. When I look at who these people were, I tried to figure out what their motivation was. So that's what the three categories are based on.

You have people like [Oracle chairman and founder] Larry Ellison, who are really tough, cutthroat characters. They are not easy to deal with. They have giant egos. These are the “glorious bastards.” What motivates him is winning. He wants to win, and he wants to win above all else. One of the things he understands is if you want to win, you need to have the world's best teams, and that's the big driver. He'll do everything he can to find great people.

“Nurturers” are the ones we might think about more often. Why do they care about doing this? Because they care about legacy. They enjoy the fact that they are helping other people advance their careers.

The third category are the creative types — I call them “iconoclasts.” Miles Davis is the most unusual of those examples. These are people who become real magnets in and of themselves. They attract really good people to their circle who want to keep learning, and because they want to learn, too, they end up teaching other people at the same time. For them, the motivation comes out of the natural activity of performing and creating — whatever their art happens to be.

Q: But what distinguishes these folks from those who are simply a good manager?

A: While good bosses do some of the things superbosses do, they very seldom do so many of them. They don't go as deep, they don't go as far.

It's one thing to be a mentor and provide a little guidance, but the degree of involvement of a superboss with someone on their team is much more intense and long-lived than the typical mentorship experience.

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