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Do You Have What It Takes to Become a Superboss?

Career Entrepreneurship
Do You Have What It Takes to Become a Superboss?


  • Which lesson all companies could learn from Saturday Night Live
  • How to become a talent magnet for your industry
  • How a legendary NFL coach chose an unknown player over a highly-touted one—and got it right

Sydney Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dart­mouth College and the di­rector of Tuck’s Center for Leadership. A consultant and speaker to senior execu­tives around the globe, he is listed in Thinkers50, the world’s most prestigious ranking of leadership gurus. Author and award-winning podcaster David Burkus recently hosted him on Radio Free Leader to talk about the surprising makings of a “superboss,” and what steps we can all take to become one ourselves.

David: How did you transition from studying the terrible decisions that people make to studying superbosses that attract and grow talent?

Sydney: After writing a couple of books on failure, I felt like there was more to the story that I hadn’t really gotten to. If there’s one thing that you need to do to thrive and live longer as an organization, it’s the ability to generate and regenerate talent on a continuous basis.

And that realization got me to think, “Well, who’s good at that?” That brought me to Alice Waters, the famous chef and restaurateur from Chez Panisse in Berkeley. She pretty much created, or resurrected, the organic, farm-to-table local sourcing of high-quality food, and if you look at the number of people that worked for her [and later] opened up their own restaurants, it’s in the hundreds. I said, “Okay, let me figure out what it is she did,” and then I started asking, “Well, who else is there?”

I started looking at one industry after another, from the National Football League, to jazz, to consumer packaged goods, to hedge funds, to advertising, to American comedy—really diverse industries. And in every industry I looked at, I was able to identify one, sometimes two, but mostly one person that had this outsized influence on the development of great talent. And those were the people that I came to call “superbosses.”

David: That’s an interesting insight, because I’ve found that the moment you lay out some best practices or evidence-based suggestions to people, one of the most common responses is, “Well, yeah, that works great for this, but it would never work in our industry.” One of the things I like about these superbosses is that they come from every industry, sector, company, and geography. There are things that are tried and true, regardless of where you find yourself in a leadership role.

Every industry is made of people, right? So people are a lot of times at the core of these problems. It’s not like your industry would be exempt from that, unless your industry is run entirely by robots. But if it was, we wouldn’t be talking about how to attract, retain, develop talent.

Speaking of talent, one of the traits of superbosses is that they look for talent in unlikely places, or they look for new, untapped pools of talent. Tell us about how you found that insight.

Sydney: Well, every large company has sophisticated HR practices and standard methods. But superbosses… They’re not against any standard methods, but they also add their own thing. They’re talent spotters, always on the lookout for great talent. I interviewed hundreds of people for this research, and you keep hearing the same story, in some version or another.

“They’re not stuck to following the job description and saying, ‘Who checks the most boxes?’ They’re looking for people that check boxes they haven’t even thought about.”

One story was about Bill Walsh, the San Francisco 49ers head coach who won three or four Super Bowls in his time. One year, he went to recruit a highly touted quarterback, and he went out to see him practice. The quarterback was throwing some passes to his roommate, who was just helping him out. The roommate was on the football team, but not a star or anything like that. Walsh is watching, spending a few hours with them. He goes back, and on draft day, he ends up bypassing that highly touted quarterback and picks the guy that was catching the ball for him. And that guy turns out to be Dwight Clark, the legendary 49er receiver who made the catch in the end zone to win a Super Bowl.

When [superbosses] find someone, they’re willing to create an opportunity for them. They’re not stuck to following the job description and saying, “Who checks the most boxes?” They’re looking for people that check boxes they haven’t even thought about. They’re looking for unusual talent, and to do that, you’ve got to look for it in different places—diamonds in the rough, if you will.

David: I love that insight, that when they find that talent, they’re willing to adapt the job, or even adapt a division of the organization, to fit that talent. They don’t see it as just, “We have this box on the org chart that is now empty because somebody left or got promoted, so we’ve got to find a carbon copy of that person.” Sometimes it’s, “Okay, there’s this vacancy, and there’s this really talented person. So let’s rearrange [things] to make the best use of this new talented person.” No new talent is going to be the same as the talent that created that opening. So every time there’s an opening, we have to kind of rewrite the org chart to figure out the best way to use that new source of talent.

One of the other insights I thought was really interesting in Superbosses was the effect of talent in teams, what you call “the cohort effect”—this idea that even though we’re encouraging teamwork and collegiality, we’re also encouraging internal competition. Superbosses navigate that balance perfectly, and it leads to far greater performance than if you stress one over the other.

Sydney: Yeah, within a team you want to create both collaboration and a degree of competition. One of my favorite examples of that is Lorne Michaels, the creator of Saturday Night Live. He’s been doing it for decades.

Think about that show—you have to collaborate with writers and other performers to create a skit. But as you get later and later in the week, all these skits—three hours of material—have to get winnowed down into an hour. And that, in a sense, is the definition of competition: When you have only so many seats around the table, and you’ve got way more people—or in this case, skits—[than will fit].

So if you want to succeed at SNL, you’ve got to learn to cooperate, to work with other people. But at the same time, you can’t lose a bit of that edge that [makes you] want to win—you still want to get your skit out there on Saturday night. That’s the special combination.

“Within a team you want to create both collaboration and a degree of competition.”

David: One of the other insights I thought was really cool and counterintuitive was this idea of saying goodbye. In so many organizations, if you decide to leave, that’s the end of the relationship; you’ll probably never hear from anybody again. But superbosses say goodbye on good terms, not saying, “Farewell” but “Keep in touch.” Instead of responding with anger, [they] allow that relationship to continue, even if [the departing employee] no longer serves the needs of the organization.

Sydney: Managing the flow of talent is going to be one of the biggest differentiators in business over the next decades. We know that many people are going to be looking for new opportunities. And the best people, of course, are always looking to grow. So [it’s important to] not only develop and motivate people, but also manage them out of the organization.

And you get a big bonus, by the way, when you do this—you can become known as a talent magnet. Because if you’ve had people on your team that work for you for a while and then move on and are very, very successful, that’s not a secret. People hear about that. Especially today, with LinkedIn and so much data that’s out there, it’s not hard for us to figure out what the background is of the people that have done well. So [new talent can] look for where they came from and say, “That could be a good breeding ground for me. I’m going to go see if I can connect with some of those people.”

David: Yeah, I agree. And if you’re saying farewell on good terms, they can sometimes act as a source of new talent for you. If you let them grow and [take on] a leadership role in a different company, or even a different industry, you’re now tapped through that relationship to whole areas of new talent.

Sydney: That’s absolutely right. Superbosses will even rehire some of those people after they’ve had a tour of duty somewhere else for two, four, five years. But as you say, they can also tap into the community that their former protégé are now part of.

Because you helped them get better, there’s this powerful bond. All it requires is for the boss, the leader, to continue to interact and to manage that network as a key asset. And it’s not networking 101 where you just talk to people now and then—it’s looking for business opportunities, it’s continuing to help other people even when they’ve moved on. It’s a lot more than just staying in touch.

David: I wonder if we could switch a bit… What is the best advice you’ve ever received?

Sydney: The best advice I’ve received… Pretty early in my career, I had a master’s degree. I didn’t know what I was going to do, but I ended up being hired by my undergraduate institution to be an instructor. I wasn’t doing any research [or in a PhD program]—I was just a teacher. I loved doing it, and when my two-year contract was coming up, I’d done really well. And the department chair—I still remember this meeting—he says, “You know, we’re not going to renew your contract, Sydney.” And of course, [my] heart plummeted.

“I’m firing you, and it’s for your own good.”

He said, “The reason we’re not going to renew your contract is that if you’re really serious about this, you’ve got to go get a PhD. You’ve got to learn to do research, earn your stripes. You have to accomplish more than just coming here and teaching. Even though you’re highly competent at that, it’s not enough.” That, of course, pushed me in the direction of the career I ended up having, and it would not have been possible [without that advice about] getting your credentials, paying your dues, and doing what you need to do to become an expert at something.

So the advice was, “I’m firing you, and it’s for your own good.” And it was exactly right.

David: And, “I’m firing you on good terms,” right? Which is exactly the insight we were just talking about.

What do you believe that most people don’t?

Sydney: I believe that no matter who you are—whether you’re a CEO, a president, or a candidate for president—you are very, very similar to me and just about everyone else. And it might not look that way, because sometimes people are unbelievably wealthy, and [have] different skills, and intelligence, and experiences, but they’re just people. We don’t like to get criticized, we stick our head in the sand, we procrastinate, and we have certain biases and emotions that affect our decisions. Everybody is like that.

It’s a great equalizer when you realize that, because it means that no one is truly better than you. They may have accomplished things you’ve never dreamed of, but that’s not the point. The point is about who you are as a person and what you’re made of, and when we level the playing field, it [allows] everyone to say, “You know, I don’t need to be intimidated by someone that has this incredible résumé. That’s the path they chose. But I can choose my own path, and I’m going to have an impact in my own way, in my own community, over the course of my own life.” I find that very inspiring and meaningful.

David: I’m right there with you. Even from a young age, I remember my brother would make fun of me about this, because we’d go to different rock shows, and I never got starstruck, and he always did. I was always like, “He’s just another guy. He might put his gold pants on one leg at a time, but he puts them on one leg at a time.”

Sydney: We’re talking about rock stars and CEOs and presidential candidates, but the people who shovel snow or come in to clean your office are people too, and they deserve our respect. They deserve an opportunity to accomplish goals that are meaningful for them.

We’re all born with certain skills and capabilities from our genetic makeup, and it’s what you do with those that really means something to me. If you’re born with all kinds of advantages—high IQ, wealthy family connections—what are you going to accomplish from there? And if you’re born in much tougher circumstances, what’s your contribution to the world? It’s a different contribution, but it’s just as meaningful.


This conversation has been edited and condensed. To listen to the full version, click here.

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