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By Sydney Finkelstein

(Portfolio, 261 pages, $36)

When Michael Miles was in various leadership roles at Kraft during the 1980s – serving as chief operating officer and chief executive officer – he would, on arrival at work, pick somebody at random, invite the individual into his office and, despite the pressures on a senior official, speak with the employee for about an hour. It wasn't chit-chat. Mr. Miles asked quite precise questions about Kraft's operation and the person's work, mentoring in the traditional master-apprentice style. Beyond that, he made it a point to have lunch with employees two or three rungs below him – in the cafeteria – where it would be noticed by all.

Michael Miles was, in the opinion of Dartmouth College management professor Sydney Finkelstein, a superboss, an unconventional leader we can learn from, along with a clutch of others delineated and studied in a 10-year research project. Superbosses are talent magnets, drawing people to work at their side, teaching them, and then when the protégés are ready to leave, helping them to make their mark elsewhere.

Indeed, if you study the leading lights in an industry, often they spent time with a superboss, time that was hugely influential in their career when they developed deep loyalty to their former leader and a tight bond to others who worked under their mentor, even during different time periods.

The late Bill Walsh, former coach of the San Francisco 49ers, was a superboss. As of 2015, he produced almost twice as many active National Football League coaches from his players and assistants as the next most prolific talent spawner. Other superbosses include Alice Waters, who founded the legendary Chez Panisse restaurant in Berkeley, Calif.; Lorne Michaels of Saturday Night Live fame; advertising honcho Jay Chiat; filmmaker George Lucas but also, interestingly, B-movie and sexploitation filmmaker Roger Corman, for whom many great directors and actors worked; hedge-fund notable Julian Robertson; newspaper editor Gene Roberts; comic book king Stan Lee; celebrity chef Julia Child; and U.S. presidential hopeful Hillary Clinton. Prof. Finkelstein's list tilts toward white men, but he expects that in a decade or so we'll see a better racial and gender balance.

Superbosses differ from good bosses – competent, well-meaning and effective leaders – by embracing certain practices those regular leaders don't and by doing even more of the productive things good bosses do. Superbosses don't just give employees a chance to advance but personalize those experiences rather than organizing them in a standard or lockstep way. They don't need metrics to measure engagement because they are working so closely with employees they know the engagement levels intimately. They have little interest in best practices, which seem to codify ways of doing things; they are always coming up with new ways to operate. They have intuition, drive, and magnetism that is unusual.

The superbosses differ in style and personality but Prof. Finkelstein divides them into three categories: Iconoclasts, glorious bastards and nurturers. The iconoclasts don't set out to inspire or teach others but are instead fixated on achieving their own vision, with teaching a natural outgrowth of their passion. Miles Davis was singlemindedly focused on his music, but he needed other talented souls to contribute and help him to advance – and they, in turn, learned enormously from their time in his musical hothouse.

The glorious bastards were intent on winning, not on developing others. They were selfish, mercilessly chastising others and driving them to work inhumane hours. In some ways, they reminded him of the spectacularly unsuccessful executives he identified in his excellent previous work, Why Smart Executives Fail. But although egotists – he notes it has been said the difference between superboss Larry Ellison and God is that God doesn't think he's Larry Ellison – they perceive the success of others around them as crucial to their ultimate glory and teach their people how to win.

He distinguishes the third group, the benevolent nurturers, from traditionally helpful mentors by the deep, intense relationships they develop with their younger, less experienced protégés. They are activist bosses, consistently present to guide and teach. "Would your typical corporate mentor check in with you at one in the morning to see how your big project is going? A nurturer would," he writes.

Superbosses all possess extreme confidence, even fearlessness – people for whom there are no problems, just solutions. They thrive on competition, and seek it out. They are imaginative – visionaries, who he notes "think intensely about what could be and are fired up to turn their dreams into reality." They all have integrity, not just honesty but a core vision or sense of self, avoiding playing games as some bosses will.

They are a fascinating lot, well chronicled in the book, which will inspire you to re-evaluate your bosses over the years and how you can improve your own leadership. It's engaging and easy to read, driven by stories of the superbosses he studied, but at the end he tries to tease out lessons that we lesser folks can apply.


Driven to Delight (McGraw-Hill, 282 pages, $33.95) is another in a series of books by consultant Joseph Michelli looking at highly successful companies, this time Mercedes-Benz and how it delivers its celebrated customer experience.

Consultants Robert Anderson and William Adams share their integrated framework for becoming a more successful executive in Mastering Leadership (Wiley, 342 pages, $36).

Consultants Warren Shiver and Michael Perla explain how to improve your sales performance in 7 Steps to Sales Force Transformation (Palgrave, 197 pages, $44.95).

Harvey Schachter

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