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Are You a Superboss? Here’s How to Tell

You’re a good boss. You care about your people. You have vision. You inspire others. But do you have what it takes to be a “superboss”?

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October 13th and 14th, 2016, Cincinnati, Ohio
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“A ‘superboss’ is a whole different kind of leader,” says Dartmouth business school professor Sydney Finkelstein, who studied leaders in a variety of industries—football coach Bill Walsh, CEO Larry Ellison, television executive Lorne Michaels, to name a few examples—for his 2016 book, Superbosses: How Exceptional Leaders Master the Flow of Talent. He discovered a certain type of leader to be remarkably proficient at finding, nurturing and inspiring outstanding people, who then go on to become highly sought after leaders themselves. Like other CEOs, these “superbosses” are smart, driven, confident. But there are also very specific characteristics that set them apart:

  • They hire differently. These honchos are always on the prowl for talent and have a preference for the unusual candidates, those individuals who may not check all the formal qualifications boxes but who have unique backgrounds or experiences, who’ve shown they excel at innovation and out-of-the-box thinking. “You see this pattern of people working toward creating a science of talent and identifying standard best practices,” says Finkelstein. “Superbosses fight against that.” Rather than hiring to a job description, the superboss will create a position to fit the talent, often selecting people he or she has met via some unusual channel. “HR will say that’s a no-no,” adds Finkelstein. “But then, why wait for this talent to walk through our door? Why not go out and seek it?”
“Rather than hiring to a job description, the superboss will create a position to fit the talent, often selecting people he or she has met via some unusual channel.”
  • They inspire at a whole different level. Like other managers, superbosses set high expectations and put plenty of pressure on their direct reports to achieve them. But they also add one other critical ingredient: they’re able to inspire their people to believe they’re special and that there’s nothing they can’t do. “When people believe that, they perform better,” says Finkelstein. “We have somehow forgotten that very basic principle of human nature. But superbosses haven’t.”
  • They’ve resurrected the master/apprentice relationship. This once-popular method for learning craft and trade went by the wayside following the industrial revolution, but superbosses have brought back a version that leads to greater autonomy for protégés and more time for CEOs to focus on the big picture and see the disruptive influences coming around the bend in their markets. “They look for big opportunities for their people and they’re unafraid to delegate,” says Finkelstein.
  • They’re hands-on—but in a good way. The average boss typically fits into either the big-picture mold, having no knowledge of the day-to-day, or in the micromanager mold, living in the weeds with direct reports. The superboss will do both, periodically. But when he or she does dig into the details, it’s with the goal of teaching, cajoling and motivating rather than controlling, says Finkelstein.
  • They assemble competitive-collaborative teams. Again, while the average CEO would inspire people toward either collaboration or competition, the superboss manages to elicit both. The result is teams of outstanding people working in concert to achieve the boss’s vision, but also individually driving forward to be the best of the pack.
  • They say goodbye nicely. The classic response when top talent leaves for another opportunity is to lament the company’s investment in that person and to experience it as a betrayal. Not superbosses. They wish their protégés well, maintaining close ties with them and viewing them as potential assets to be leveraged in the future. They know they’re creating world-class talent, says Finkelstein, so they know those individuals may seek new opportunities. “What we’ve found is when you stop fixating on retention and focus more on pushing people and accelerating their careers, even if it means they’re going to leave at some point, you end up retaining talent longer than you otherwise would have.”

Professor Finkelstein will dig deeper into the differentiators that turn bosses into superbosses at the CEO Talent Summit on October 13 in Cincinnati. Following his talk, he’ll lead a panel on “Improving Employee Alignment and Engagement Across Generations,” featuring top executives from Vonage, Sealed Air, and KPMG. For more information and to register, visit To learn more about Professor Finkelstein’s work, visit To order his book on Amazon, click here.

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