How I realized the incredible impact great bosses have

Photo credit: Sascha Erni

“I don’t care if you have to take drugs, you have to build it in six months,” said my boss, Khurshed Birdie, when I told him that he was on drugs if he thought my team could create a software development toolset in less than three years. This was in 1986 at Credit Suisse First Boston, one of New York City’s top investment banks. We were rebuilding the company’s trade processing systems to run on a client–server model of computing. This technology is common now, but then it was as futuristic as “Star Wars.”

He bet a $100 million project on my vision.

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.

Taking chances on the unconventional ones

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.

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.”

Superbosses take chances on unconventional talent.

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.

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.

Caring about your success

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.

They help people accomplish more than they’d ever thought they could.

Trust and delegate