Three Traits of Successful ‘Superbosses’ – and One to Avoid

Sydney Finkelstein ’88 researched successful, high-profile managers to understand how they helped their businesses flourish. Here’s what he learned.

Ever since publishing Why Smart Executives Fail in 2003, Sydney Finkelstein ’88 has been asked the same question again and again by eager up-and-coming managers: “‘How do I avoid being in your sequel?’”

So Finkelstein, the Steven Roth Professor of Management at Dartmouth College’s Tuck School of Business, and faculty director for both the Tuck Center for Leadership and the Tuck Executive Program, decided to find an answer to that question. He researched various successful, high-profile managers and looked for clues as to how they helped their businesses flourish. “Over time, I came to realize that … the only way to survive as an organization, to thrive in the long term, is to generate and regenerate talent on a continuous basis,” Finkelstein says. “In one industry after another, I found a whole bunch of people who turned out to be tremendously good at spotting [and nurturing] great talent. I call them ‘superbosses.’”

In the resulting Superbosses: How Exceptional Leaders Master the Flow of Talent, published by Portfolio/Penguin in February, Finkelstein shows how a number of famous executives — from television producer Lorne Michaels to chef Alice Waters to football coach Bill Walsh to fashion icon Ralph Lauren — were acutely aware of the benefits of supporting their people and put a lot of thought into how they hire, motivate, inspire, and coach them. In short, these leaders would “help other people accomplish more than they ever thought possible,” Finkelstein says.

The good news is that everything in the superboss playbook can be taught, Finkelstein adds. “All it requires is a really open mind and a willingness to start thinking differently about how you manage people,” he says. It also entails a healthy dose of patience. “It’s not that somebody who wants to adopt what the Lorne Michaels and Ralph Laurens of the world have done is going to be able to do it overnight. But [those superbosses] didn’t do it overnight, either. It took years to get to where they are. You can start small, pick one, two, or three specific techniques or ideas, and learn how to apply them to your own particular business or context. Then go from there and keep growing.”

Here, Finkelstein shares, in his own words, three techniques of successful superbosses — and one behavior to avoid.

• Be open to finding your next employee anywhere.

Superbosses go about looking for talent in unique, creative ways. Most organizations follow standard hiring processes: you’ve got the job description, you collect a bunch of resumes, and you do some interviewing. You end up hiring the person who checks the most boxes. Superbosses will do that too, but they’re also always on the lookout for talent. In fact, they will create a job for someone without an initial job description, which in the world of HR is one of those no-nos, but they’ll do it if they see a tremendous talent. Ralph Lauren, for example, [hired] a woman that he and his family met at a burger restaurant in New York. They started talking and he was struck by how she was dressed and how she carried herself. He ended up saying, “Come by the office; I want to offer you a job.” Just like that. The woman worked for Lauren for five years as a creative muse, without a formal job title. Superbosses don’t get hamstrung by [conventional] HR methods.

• Champion the brand — and the people.

Everybody wants to be a winner, and superbosses absolutely instill that sense of confidence. They truly inspire people. They really make people believe that they can accomplish anything. They create this sense of, “I have a really great track record, and the fact that I picked you — or that I kept you, if I inherited you on my team — is because I think you’re special. I think you can accomplish unbelievable things.” Ralph Lauren used to say, “The whole world looks at us. They follow us. We set the standards.” He really believed it, and he conveyed that message, and that generated energy and excitement among his people.

• Take talent under your wing.

Superbosses have resurrected the apprenticeship approach, and that means that they’re going to roll up their sleeves and work with their people. They’re always teaching, and they’re customizing what they’re doing, in the sense that they spend the time to understand how everyone in the team is a little different and can be motivated in a different way. They’re really hands-on in how they interact with people.

• Don’t take your people for granted.

Bad bosses — smart executives who fail — have a tendency to look at their teams as people who they can use for their own benefit. They can just work them hard, claim all the credit, not worry about developing them or helping them get better, and just wash them out, burn them up, and go get some new ones. That game can only go on for so long before you start to gain a reputation in the company or in the industry, and it becomes tougher to hire that great talent. Because of your attitude, you end up making some really big mistakes.

Superbosses are not at all like that. It’s not that they can’t be demanding, because they are, but they really understand that to win, you need the world’s best teams. That’s their pathway [to success], and so they do everything they can to help other people get better. And one more thing: a lot of superbosses truly value this idea of legacy, of leaving something behind when you’re gone and of really making a difference. It’s a pretty powerful idea.

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