The result was that my team worked day and night to build a technology that became the foundation of the company’s information systems. It gave Credit Suisse First Boston a competitive edge and led IBM to invest $20 million in a spinoff company that was formed to market the tools we had developed.

I was a lowly computer programmer — analyst when Birdie hired me: a computer geek who didn’t own any three-piece suits, white two-ply cotton shirts, or wing-tipped Oxford shoes — the uniform of investment bankers. Yet I was hired on the spot. I had some far-out ideas about how computer systems could be built — but didn’t believe for a second that I could implement them. My boss did: he believed in me more than I did, and he bet a $100 million project on my vision. He allowed me to expand my team from four to fifty-five people and shielded me from criticism by other teams who had to use my tools to build their systems — and who thought I was crazy. There were a lot of problems along the way, and Birdie allowed me to learn from my mistakes. And then he promoted me to vice president of Information Technology when I achieved success.

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Birdie was what Sydney Finkelstein, a Dartmouth business professor, in his new book, Superbosses: How Exceptional Leaders Manage the Flow of Talent, calls a “superboss.”

As Finkelstein explains, superbosses take chances on unconventional talent. Oracle’s founder, Larry Ellison, hired candidates who had accomplished something genuinely difficult, rather than those with formal qualifications, because he believed they would rise to the technical challenges. Designer Ralph Lauren offered jobs to strangers whom he met while dining in New York City restaurants. Superbosses take raw talent and build self-confidence. They hire for intelligence, creativity, and flexibility — and are not afraid of people who may be smarter than they are.

Under Finkelstein’s definition of superbosses, Birdie would be categorized as a “glorious bastard”: someone who cares only about winning. Deep down, he had a good heart — but was ruthless in setting expectations and driving people to work extremely hard. I’ll never forget him telling me that “Christmas was an optional holiday.” These bosses realize that to get the very best results, they need to drive people to perform beyond what seems reasonable and achievable.

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Even though I achieved a lot, I hated working for Birdie, because I had to neglect my family for months on end. This isn’t something I would ever do to my employees. My next boss, Gene Bedell was very different. He left his job as managing director of information technology in order to found Seer Technologies, the start-up that IBM had funded. Bedell convinced me to leave my high-paying investment-banking job to join him in a number-two role, as chief technology officer, at the low-paying, high-risk, startup.

Bedell was what Finkelstein calls a “nurturer”: someone who coaches, inspires, and mentors. These superbosses take pride in bringing others along and care deeply about the success of their protégés; they help people accomplish more than they’d ever thought they could.

Bedell managed by a method he called “outstanding success possibilities.” He challenged his executives to set ultra-ambitious goals and then find unconventional ways to achieve them. Instead of managing to what was achievable and possible, we shot for the impossible. And then did whatever it took to get there — without worrying about failure or looking back. It is amazing what you can achieve when you have a single-minded focus. We took Seer Technologies from zero to $120 million in annual revenue and an IPO in just five years — faster than any other software company of that era, including Microsoft and Oracle.

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Superbosses create master–apprentice relationships. They customize their coaching to what each protégé needs and are constant fonts of practical wisdom. Bedell taught me how to sell. A year after the company was formed, he sent me to Tokyo to sell IBM-Japan on an $8.6 million deal to fund the creation of a Japanese version of our product. I didn’t think that a techie like me could do these things; he taught me that selling was an art that could be learned and perfected. I helped our salespeople close more than $200 million in software deals. And that is another skill that superbosses have, building what Finkelstein calls the “cohort effect”: teamwork and competition combined. Lorne Michaels, for example, who created Saturday Night Live, judged writers and performers by how much of their material actually went to air — but they had to do it with the support of their coworkers, the people they were competing with.

A common trait of superbosses is the ability to delegate work and build jobs on the strengths of their subordinates. They trust them to do their jobs and are as supportive as can be. They remain intimately involved in the details of the businesses and build true friendships. Bedell often invited my family to his vacation home near the Outer Banks of North Carolina. He took me to Skip Barber Racing School to learn how to race a Formula Ford, and built a gym in his basement so that his executive team could lift weights together.

You will find the alumni of our project at Credit Suisse First Boston and Seer Technologies in senior leadership roles now, at companies such as IBM, PayPal, American Express, and every one of the top investment banks. Many started their own companies, as I later did. There are literally hundreds of people who built successful careers because of my two superbosses. When I became an academic later in life, I was fortunate to have two superboss deans at Duke’s Pratt School of Engineering, Kristina Johnson and Tom Katsouleas, who nurtured me. Superbosses aren’t just in corporations — they can be found everywhere.

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