The Makings of a Superboss

It’s taken 30 years, but Sydney Finkelstein knows a superboss when he sees one now — all thanks to thousands of interviews he and his research team have conducted with exceptional leaders.

Growing up in Montreal, Finkelstein studied economics at Columbia University in New York and opted to stay in the U.S. after his graduation, working as an academic and professor at the Tuck School of Business at Dartmouth College in Hanover, N.H..

Your Workplace caught up with Finkelstein more recently to get to the heart of what, he would surmise, makes a superboss tick.

Kuropatwa: What academic field did you study and why?

Finkelstein: Business Strategy. It was partly psychology, partly sociology and partly economics. I’ve always been interested in why people do what they do, why they make the decisions they make — especially people who are highly influential or powerful. And that’s why I ended up gravitating toward the business side. Senior executives have a tremendous amount of influence on society, so that’s why I picked that.

How long have you been researching ways to learn from successful executives?

It’s been 30 years from PhD to now. I’ve talked to thousands of managers for research and for teaching, and have been teaching probably tens of thousands of managers by now.

Do you find that you’ve learned enough?

The learning is pretty constant. It never ends. There are always new companies and organizations doing things that they either want your advice or feedback on or that raise questions that you might get interested in. In fact, I probably need two or three lifetimes to do all the projects I have in mind, even now.

Why did you choose this topic of superbosses?

It was an outgrowth of the earlier book I’d written on failure, Why Smart Executives Fail. After that book came out, I did a lot of work with companies, and the same question kept coming up that made me think there’s more to the story. And the question was something like, “How can we, as an organization, survive and thrive in the long term?” Over time, I realized that probably the single most important thing you can do to accomplish that is to be able to generate and regenerate talent on a continuous basis.

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