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How Superbosses Can Transform Your Talent Strategy

For Dartmouth professor Syd Finkelstein, “glorious bastards” such as Larry Ellison, “iconoclasts” such as Alice Waters, and “nurturers” such as Jon Stewart are models for the next generation of leadership development.

What did the renowned San Francisco 49ers head coach Bill Walsh, who passed away in 2007, have in common with leading fashion magnate Ralph Lauren? Both are examples of what Syd Finkelstein, management professor at Dartmouth College’s Tuck School of Business, calls superbosses: leaders who help their own subordinates realize their own leadership potential. The ability to attract and develop great people is a fundamental requirement for any organization, and in his book Superbosses: How Exceptional Leaders Master the Flow of Talent (Portfolio/Penguin, 2016), Finkelstein explores why some people seem to have a knack for it.

It turns out it’s not a knack; it’s the natural result of habitual on-the-job practices. By interviewing hundreds of people over a 10-year period about the bosses and mentors who changed their lives, Finkelstein developed a list of 18 people who had advanced the careers of other people. As he sought out the common elements in their cases, he uncovered a template for bringing out the best in the organization around you. Besides Walsh and Lauren, the superbosses include Alice Waters, founder of the legendary California restaurant Chez Panisse, where many well-known chefs began their careers; television producer Lorne Michaels, whose Saturday Night Live has long been a launching pad for celebrated on-camera and behind-the-camera talent; and Intel cofounder Robert Noyce, who mentored many of Silicon Valley’s celebrated entrepreneurs. Rounding out the list are restaurant format designer Norman Brinker, advertising legend Jay Chiat, filmmaker Roger Corman, jazz trumpeter Miles Davis, Oracle CEO Larry Ellison, Hospital Corporation of America cofounder Tommy Frist, Star Wars creator George Lucas, the late Kraft Foods CEO Michael Miles, Milken Institute founder Michael Milken, Kuopio Symphony Orchestra conductor Jorma Panula, Philadelphia Inquirer executive editor Gene Roberts, hedge fund titan Julian Robertson, and real estate developer Bill Sanders. (The list is heavily weighted toward men, says Finkelstein, because women have only recently become executives in large numbers. Only a handful of women bosses have produced a chain of protegés. The book does mention several women superbosses besides Alice Waters, including chef Julia Child, pop musician Lady Gaga, Texas politician Ann Richards, Facebook executive Sheryl Sandberg, Snapchat executive Emily White, and television magnate Oprah Winfrey.)   

Finkelstein sorted the leadership styles of superbosses into three categories, based on their personalities. Glorious Bastards (such as Chiat, Corman, Ellison, Milken, and Robertson) do anything to win, and thus raise the bar for others who work with them. Nurturers (Brinker, Frist, Miles, and Walsh among them) lead through direct mentorship, paying close attention to their direct reports and helping guide them to more lasting careers. Iconoclasts (including Lauren, Lucas, Michaels, Noyce, Panula, and Waters) lead by example, and are most often found in the creative industries.

According to Superbosses, each of these three personalities has its own style of coaching and relationships, but all three can foster talent on an ongoing basis. If you can understand how to replicate their abilities, then you can create a new organizational playbook in your company. In that way, understanding the attitudes and impact of superbosses could lead to a new concept of learning and development. “There’s a real need for a new look at the world of competency models and how to identify — or even better, create — high-potential talent,” explains Finkelstein.

For this interview, Finkelstein sat down with strategy+business and PwC global retail and consumer leader John G. Maxwell in New York to discuss how to scale up the superboss premise. The result of doing so could be an organization full of superbosses, following a playbook based on unbridled commitment — whether to the people (nurturers), to the intrinsic value of the work (iconoclasts), or to building a wave of success (glorious bastards) that sweeps everyone in the enterprise along with it.

S+B: How did Superbosses come to be written?
About 12 years ago, I wrote a book called Why Smart Executives Fail and What You Can Learn from Their Mistakes [Portfolio, 2003]. After it was published, I met many businesspeople who wanted to know how to avoid the problems I had talked about. I realized there was a theme I had not fully appreciated: What really differentiates an organization that thrives over a long period of time? For me, this was the ability to generate and regenerate talent on a continuous basis. So I started thinking, “Who is really good at that?”

I began with the high-end restaurant business, which is an interest of mine. I knew Alice Waters at Chez Panisse. I realized just how many people who have been through her kitchens as assistant chefs, bakers, and even busboys have gone on to run hugely successful restaurants. Of course, it’s not shocking that a sous chef might leave a restaurant to open up his or her own, so I looked at the National Football League [NFL].

Because of the amount of data collected about sports, you can be more precise [in your research] than in most other industries. I identified the head coaches of teams that made it to the Super Bowl, and did a genealogical-style study of their careers — to see who they had worked for. Bill Walsh from the San Francisco 49ers was the primary spawner of talent in the sport — more successful than any of the other famous coaches in his era or even after him.

In the 2015–16 season, for example, out of the 32 teams in the NFL, 20 had a coach who came from the Bill Walsh tree of talent. That’s stunning. He left the NFL in 1989 and has been gone since 2007. Yet his legacy as a superboss remains.

Then I started systematically studying the genealogy of other industries, advertising, fashion, consumer packaged goods, hedge funds, and news media among them. In every industry I studied, I found there was almost always just one person who had tremendous influence in the development of talent over time. The proof was in the chain of other great bosses and performers who mentioned them as pivotal figures.

Once that pattern emerged from the data, it raised fundamental questions. What did these people do to account for their tremendous success as talent spawners or superbosses? What were the key elements that differentiated what they did from what other leaders did?

S+B: You ended up dividing them into three personality types. Would you agree that the three types share an unusually strong emotional connection to their work?
Yes, that’s right. The differences among them were mostly in the type of motivation they had.

For example, nurturers care about developing other people; they are thinking about their own legacy. The iconoclasts, like Miles Davis, don’t really think in those terms, but they organically attract interesting, ambitious people who want to learn from them and with them. Iconoclasts welcome these talented people into their circle because it improves their own work. Developing talent is a side effect.

Then the third type, the glorious bastard, typically couldn’t care less about developing other people. But they are totally driven to win, so they need the world’s best people and teams. They do everything they can to make that happen.

So the reasons for being a superboss varied significantly among the three types, but they all did pretty much the same things.

S+B: What were those things?
In the book, I describe what they did as the “superboss playbook.” It includes an intensive and idiosyncratic kind of recruiting; they look for people who “get it,” who are so skilled or smart they can teach the boss something, rather than people who fit the formal requirements of a job posting. Superbosses take chances on people, and tolerate more churn if it means finding the right people later. They drive themselves and their people hard, inspiring people with huge aspirations, and they expect world-class excellence from themselves and everyone around them. They create safe spaces where people feel free to try out ideas, even if they fail. To do this, they have to build close-knit, collaborative, mutually supportive teams, but they also encourage fierce competition among the people who work for them. They’re open to change and willing to break with industry norms, and if an employee makes a suggestion that works, they consider it and often take it forward. They embrace an apprenticeship model, making sure that promising junior employees get close exposure to the way they work and to other masters on the team. They’re always teaching. They downplay executive perks. They continuously prowl around their own organizations, looking for people who can take on more responsibility, and giving it to them. And they network relentlessly, especially with people who have moved on to other organizations.

S+B: Can you scale these ideas? Can you institutionalize superboss-style habits in a company?
I think you can. Just as you can grow palm trees in a heated greenhouse, you can scale these practices by creating a business environment that’s especially amenable to them.

Step one would be doing an audit of where you are today to find out whether your managers or leaders are already superbosses. Look for strong and capable people, and ask them who in the organization has helped them build their careers, or who they’ve learned from. Consider doing a more formal assessment of the strengths and weaknesses of your managers, using the key attributes of the superboss playbook. Also look for your existing barriers and accelerators — not just to mentorship, but to close engagement in the work, in the manner of an iconoclast or a glorious bastard.

Then build a coalition of people who are superboss-like and have them meet and learn from one another. Develop a curriculum that can be cascaded into the organization. Don’t forget to build incentives that recognize and reward superbosses. For example, if the rewards are driven only by financial performance, it is more difficult for some leaders to employ superboss techniques.

“If the rewards are driven only by financial performance, it is more difficult for some leaders to employ superboss techniques.”

If you do all this, it opens the door to broader impact than one-on-one coaching has.

You also need to pay attention to the criteria used to hire people and make sure you’re including factors that superbosses have found to be particularly valuable, such as creativity, open-mindedness, flexibility, and competitiveness.

S+B: What’s the ideal number of superbosses for a company to have?
There’s no maximum percentage. Of course, you’re better off with more rather than some. Superbosses get far more out of their teams than other leaders do, in terms of performance, innovation, creativity, and teamwork. Thus, the more superbosses you have, the stronger your teams will be.

S+B: Would you want to report to a superboss yourself?
Yes. A superboss creates a world in which each individual manager has a gigantic opportunity to make a difference. People talk about how exciting and energizing it is to work for a superboss, how much opportunity and challenge they are given, and how much is accomplished. Personally, I would love the creativity and open environment that a superboss makes possible.

“If you’ve had a superboss yourself, you have more experience with effective management, and you’re likely to do better as a leader.”

The benefit of reporting to superbosses is particularly evident when people become supervisors for the first time. This is often a stage at which people wash out. So many problems crop up: micromanaging, often by taking over a subordinate’s work because you know you can do a better job; not having sufficient interpersonal skills; or lacking understanding of just what an effective manager should do. This is another place where assessing first-time managers against the superboss playbook could pay big dividends. If you’ve had a superboss yourself, you have more experience with effective management, and you’re likely to do better as a leader.

In most companies, when people are identified as high-potential leaders, there should be some element of the superboss playbook in that selection. There’s a real need for a better concept of leadership competency, and I think the superboss model, injected into talent development and recruiting, could be particularly helpful.

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