Superbosses | Book Review

Sydney Finkelstein’s meticulously researched masterwork, subtitled How Exceptional Leaders Master the Flow of Talent, is a necessary resource for anyone concerned about developing people and teams.

Tracing talent sources, Finkelstein notices (p. 3) genealogical “trees:”

“If you looked at the top fifty people in these industries, you would find that perhaps fifteen or twenty had once worked for or had been mentored by one or a few talent spawners – or ‘superbosses.’”

Found in numerous industries and fields, Finkelstein focuses on a primary list of eighteen: Lorne Michaels, Ralph Lauren, Jay Chiat, Larry Ellison, Bill Walsh, Jorma Panula, Bob Noyce, Bill Sanders, Miles Davis, Michael Milken, Michael Miles, Alice Waters, Norman Brinker, Roger Corman, Julian Robertson, Gene Roberts, George Lucas, and Tommy Frist.

Rather than Bossy Bosses (e.g. Donald Trump), superbosses look fearlessly in unusual places for talent and lavish responsibility on inexperienced protégés, taking risks that seem foolish to others (p. 6). Finkelstein notices many of the best bosses today tend to think of themselves as professional managers (p. 7), not leaders, and confesses his biggest discovery over time studying organizations is it really is about the people (p. 9). Finkelstein’s work systematically and empirically studies what really motivates, inspires, and enables others to achieve their full potential.

Chapter one defines superbosses and the following seven chapters (p. 9) offer a “superboss playbook – or the techniques, mind-sets, philosophies, and secrets the world’s best bosses use and other’s don’t.” Each playbook chapter concludes with useful application (…like a superboss) ideas.


Superbosses (pp. 14-15) fuel the talent for an entire industry by making other people successful. They can make any organization attractive (p. 18), quantitatively (tally successful protégés) and qualitatively (boss’s reputation). Finkelstein cites Bill Walsh as an excellent controlled environment case study (pp. 16-17), producing a dominant number of National Football League (NFL) coaches.

“If you’re a senior leader interested in creating a never-ending pipeline of world-class employees, these are the kinds of bosses you want to seek out, support, and multiply in your organization.” (p. 21)

Superbosses fall into three distinct patterns: Iconoclasts, who care about their work and their passion, such as Miles Davis, and are often artistic. Next are the Glorious Bastards, who care solely about winning, and know they need the best people to win, such as Larry Ellison, who has spawned a breadth of talent in Silicon Valley. Last, are the Nurturers, or activist bosses, who consistently guide and teach their protégées, such as Bill Walsh (pp. 25-29).

All superbosses hold common character (leader) traits including extreme self-confidence (fearlessness), competitiveness, imagination (visionary), integrity (core vision or sense of self) and authenticity (pp. 30-31). Finkelstein discovers they had their own unique and often counterintuitive (p. 34) behaviors – a clear, powerful “playbook.”

Showcasing the common habits of superbosses, Chapters 2-7 align strongly with coaching and use of one’s Personal Leadership Philosophy, and form this review’s focus.


Finkelstein recognizes superbosses deeply know their employees or team members, in stark contrast to (think Undercover Boss) clueless, distanced bosses, their complete antithesis (p. 110). Similarly, traditional managers (p. 111) often talk about coaching, but don’t actually spend their time that way. At a minimum, any leader must include coaching as a High Payoff Activity. Going further, superbosses disdain anything that might create (p. 113) physical or even emotional distance (e.g. corporate perks) from those in their charge.

What superbosses give protégés, then, is something quite rare in professional life, an opportunity to rebrand themselves (p. 133), or the ultimate alignment of one’s traits and abilities (think Energize2Lead, or E2L profile) with not just a job, but also a lifetime path. In the deepest sense, superbosses blend coaching with mentoring (mastery advocate), finding a third path between micromanagers, who are afraid to delegate because they don’t trust their subordinates, and free riders, who (p. 140) delegate without control because they are lazy or incompetent. Finkelstein shares a major theme: They [superbosses] will ultimately push protégés to step up and take responsibility for their own development (p. 143).

Another was to think about superboss coaching is lifetime coaching, in part because it’s a two-way street (p. 178), leading to networking long past working in the same organization. Finkelstein shares that some superbosses create completely new businesses for them [protégés]  to run (p. 182). Frequently this results in a hodgepodge of formal and informal relationships that can only be described as idiosyncratic (p. 185).

Personal Leadership Philosophy

Imagine amplifying your Personal Leadership Philosophy with a superboss vision, in Finkelstein’s terms; without exception unique, authentic, and consistent. Like Dan Pink, Finkelstein finds money doesn't (p. 75) fully motivate most people. Instead, as leaders we should answer questions such as: Why does [our] organization exist? or Why does [our] team exist? (p. 77), essential elements of a Leader’s Compass, with concepts such as continuous improvement or insatiable curiosity.

On page 84, Finkelstein notes that aside from their primary vision, superbosses encourage rethinking virtually everything else about their jobs, or put another way, protect the “Why,” while everything else may, if not should, be changed or discarded. Not surprisingly, innovation is the DNA of superbosses (p. 88), as they energize (p. 98) people around them, just as we find in our Leadership Philosophy Workshop. Finkelstein identifies a mindset of change (pp. 98-99), rather than a process or reaction (e.g. Kotter or Collins).

Operating principles and priorities are clear to a superboss, exemplified by “There’s something special about an environment (p. 151) in which nobody is more important than the show.” Likewise, superbosses ardently support and reinforce their protégés sense of themselves as a “chosen people” by constantly reminding them that they can accomplish anything if they set their minds to it (p. 154).

“Get It”

Chapter two, Getting People who “Get It,” warrants special mention and reinforcement. We cannot be coaches, live a Personal Leadership Philosophy, or become a superboss, without a fundamental understanding of people. Envision understanding a person’s E2L profile as a starting point, never stop learning more, and make it a top priority:

 “If your schedule is filled with meetings, how much time do you actually spend asking opinions, affirming abilities, establishing employees’ status as members of an A team, alerting them to the underlying purpose behind short-term priorities and objectives, and so on?” (p. 77)

Final Thoughts

Finkelstein’s concluding reference chapter contains numerous ideas for adopting superboss strategies into our personal leadership philosophy, our organizational culture, and our day-to-day lives. A great list of ten questions for both seasoned managers and younger, first-time managers is found on pages 201-202.

Note: Sydney Finkelstein generously provided a copy of his book for review.

JE | April 2016