Sydney Finkelstein on What Makes a ‘Superboss’

The influence of a boss can reach beyond simply managing people.

'Superboss'

Picture the most influential and successful leaders in a given industry, and it’s very likely that a great majority of them at one point or another were led by the same select set of special leaders.

To Dartmouth professor and author Sydney Finkelstein, these people have a special title: “superbosses.” Both Tina Fey and Jimmy Fallon, for example, have established themselves as leaders in the world of comedy thanks to the nurturing they received from “Saturday Night Live” creator and Superboss Lorne Michaels.

Oracle cofounder and former CEO Larry Ellison is another so-called Superboss, having developed the likes of Salesforce.com CEO Marc Benioff, among other executives in the technology industry.

Superbosses — also the title of Finkelstein’s most recent book — are different from regular bosses because they enable people to accomplish more than they ever thought possible. What’s more, these people in many instances go on to become superbosses themselves.

Talent Economy spoke with Finkelstein about the unique powers of superbosses. Edited excerpts follow.

What is a “superboss?”

A superboss is someone — a manager, a leader, a boss — who helps other people accomplish more than they ever thought possible. And as a result, they accelerate the careers of their protégés. What makes them stand out, of course, is their track record in spawning talent. In fact, if you were to look at the top 40 or 50 people in an industry or a sector, you would discover that a disproportionate number would have worked for the same person at some point in their careers. Those are the people that I ended up calling superbosses.

sydney finkelstein
Dartmouth professor and author Sydney Finkelstein

What qualities do they have?

Superbosses are very competitive. They are very high-integrity people. They can be uncompromising in their views of what they want to accomplish in their lives. They’re almost fearless. They’re not afraid of risks.

They have resurrected the master-apprentice approach to developing talent. If you think about it, it’s kind of fascinating because for hundreds of years, this is how people would learn their skill or their craft. Whatever it is you’re doing or that I’m doing, we would have learned it working for a master, and we would have started as an apprentice. For the most part, that system has gone by the wayside.

In the book, you say superbosses encourage protégés to rethink aspects of their jobs. How?

Superbosses themselves rethink their jobs in that the job of a superboss — the way superbosses define their own job and the way that a superboss works with people on their own teams — is to kind of try to take off the blinkers among people.

Most people have a job, they put their head down, they go ahead, and they do it. And if they do it, they get a pat on the back. Superbosses expect you to do whatever your job is, but they also want you to be redefining in the sense that you’re always looking for new things to do.

How do superbosses integrate innovation in their work?

One is kind of informal. Superbosses will work closely with people on their team. Let’s say you’re working for me. I will be periodically be sitting with you at your cubicle, your office, if you’re on the road, and I will be challenging your thinking. They’re always looking for something new, and they challenge and push people.

The other thing they do is everyone who works for a superboss really knows that that’s part of the job description in a way. It might not even be a formal job description. That’s part of the “job description” in that you’re expected to come up with new ways at looking at the world. And that becomes more of a cultural thing.

How do bosses become superbosses?

Superbosses take the time to work one-on-one periodically with people on your team. In other words, you don’t just delegate and forget. You are hands on.

The other thing that they do is they really do set a high bar, and that is part of mentoring in that they make sure you know that the expectations are significant. And they instill a sense of confidence into you.

And all of those things are part of helping other people get better. Some are a little bit closer to traditional mentoring, but most go beyond it by quite a bit. And by the way, when people use the word “mentoring” and “mentors,” I personally don’t think that’s the right word to describe what superbosses do.

It would be a mistake for people to think, well, superbosses are just mentors that do a little bit more than your typical mentor. They do so much more and in so many dimensions that it’s best not to frame somebody’s thinking as a mentor.

A mentor will periodically check in and see how you’re doing, answer some questions. A superboss will be there much more often and won’t just ask how you’re doing but will work directly with you and will sometimes create these tremendous one-on-one opportunities, where you might be working on a project or working on an assignment that could be very intense.

That’s a good word, actually, for you to highlight: the word ‘intensity.’ It’s one of the real differentiators of working for a superboss. And it’s one of the reasons why if you work for a superboss, even for a relatively short period of time, you still can learn a lot and still get a huge benefit because of the intensity of the experience.

Time is not measured the same way when it comes to working with a superboss.