Despite claiming to be interested in hiring the best people, most managers aren’t actually comfortable with the very best. They don’t feel at ease directing employees who understand the task at hand and what it requires better than they do. They worry that employees who are too gifted will make contributions that outshine theirs. They have no idea what to do with proposals from subordinates that are too original and unexpected. They may even fear being replaced by those whom they have hired and promoted. As a consequence, most managers will unconsciously choose second-tier talent, because it is easier to categorise and deal with. They usually don’t admit this to themselves, but they describe second-tier employees as first-class talent and write off first-class prospects as oddballs.

The imperious, ego-driven “Bossy Boss” types are extreme examples of this. The last thing such bosses are able to tolerate is anyone whose skills or aptitudes might rival their own. If someone does anything genuinely impressive in their presence, they need to belittle it. When someone shows sparks of real creativity, they treat them as a misfit. Working on a regular basis with anyone who may upstage them seems to be more than they can bear.

Superbosses – those exceptional leaders who have helped spawn many of the top people in their industries – have none of these problems. They are self-confident enough to feel completely unthreatened by extreme intelligence, mind-bending creativity, and forceful personalities. They are arrogant enough to be completely oblivious to the possibility of being outshone. They have no problem with subordinates who are better than they are, perhaps because they don’t entirely believe anyone is better than they are. There’s a famous joke about Oracle CEO Larry Ellison: “What’s the difference between God and Larry Ellison? God knows he isn’t Larry Ellison.” A similar joke could be told about almost any superboss, despite the fact that some of them are deceptively mild-mannered. They all feel supremely effective and completely comfortable in their respective domains. Their status is not founded on any outward trappings. So strong is their personal sense of self that they can never be seriously unsettled by any level of ability, no matter how remarkable. In fact, they enjoy being challenged by new employees, especially if the challenge is founded on a genuine insight. If someone working for them can provide them with an opportunity to improve their understanding, do better, or come up with a better solution, they usually find it irresistible.

John Griffin, who was second in command to hedge-fund legend Julian Robertson at Tiger Management before leaving to run his own fund at Blue Ridge Capital, told me in an interview that his superboss was so eager for new ideas that he was like a “Venus flytrap saying ‘feed me’!” Robertson delighted in hiring people who “saw things in often free, new, and different ways,” people who “didn’t worry about tilting the windmill.” Larry Ellison was likewise especially proud of employees he described as “driven by a drummer only they can hear.” His reason was that “they will constantly question my wisdom, and won’t be the least bit shy about challenging me, and I hope they’ll keep me from making mistakes.” Despite falling out with some Oracle executives who questioned his judgments, Ellison seemed to relish the sort of interaction that was possible only when people were willing to argue with him. Superbosses appreciate unusual talent, not just because of the benefits that talent can bring to their company but also because they enjoy the energy boost unusual talent can provide.

Most superbosses make sure that their comfort around other supremely skilled people is publicly known. This is partly because they are proud of it, but even more so because they want the most capable people available to seek them out. Restaurateur Norman Brinker was constantly and explicitly on the lookout for executives who knew far more about something than he did. Real-estate mogul Bill Sanders liked to talk about “how many people I have hired that were four times smarter than I was.” (Source: Interview with C. Ronald Blankenship, president and CEO Verde Realty.) When superbosses see their employees shine, they feel it reflects positively on them as leaders. If their employees gain a public reputation for brilliance, then it will be easier to recruit more employees like them.

CEOs, executives, and managers are no different than anyone else. They are vulnerable to the same weakness of character that gives rise to insecurity. And just as it can keep anyone from fulfilling their potential, so too can it hold leaders back from fulfilling theirs. Superbosses provide a great example of a boss, a manager, a leader who thrives by having the self-confidence to avoid debilitating fear and insecurity. The reality is that when we allow ourselves to truly feel unthreatened by other great talent and ideas, there is so much more we can accomplish. Why wouldn’t we want to do that?



Sydney FinkelsteinSydney Finkelstein is the Steven Roth Professor of Management and Director of the Center for Leadership at the Tuck School of Business at Dartmouth College, where he teaches courses on Leadership and Strategy. He is also the Faculty Director of the flagship Tuck Executive Program, and has experience working with executives at a number of other prestigious universities around the world. He holds degrees from Concordia University and the London School of Economics, as well as a Ph.D. from Columbia University in strategic management. Professor Finkelstein has published 20 books and 80 articles, with several bestsellers, including the #1 bestseller in the U.S. and Japan, Why Smart Executives Fail.