From the Classroom to the Airwaves

Now as the host of his own show, The Sydcast, Finkelstein is the one asking the questions. 

The author of Superbosses and 25 other books, Finkelstein started his podcast in February, which features intimate conversations with fascinating people who aren’t particularly well-known. “Outside of teaching Tuck students, which is really at the top of my list, this is the most exciting thing I’m doing right now,” says Finkelstein, who is the Steven Roth Professor of Management at Tuck.

Here in an interview with Tuck News, Finkelstein discusses interview strategies, his favorite podcasts, and who he would love to interview if given the chance.      

Why did you decide to start a podcast?

I thrive on trying new things and was ready to try something different. I thought a podcast could be an interesting platform where I could engage with people in a fun and meaningful way. I’ve made a living out of asking good questions—in the classroom and in my research—so why not draw on that experience to create enjoyable content that can also give listeners new insights to business, careers, and how we live day to day? 

What do you aim to do in each episode?

My tagline is: intimate and informative conversations with really interesting people. Many of the people I talk to are local and have a Dartmouth connection. I especially like talking to people under the radar. I’m not planning to interview very many CEOs of big companies or famous people profiled in the Wall Street Journal. Lots of people do that, and they often end up hearing the usual talking points. In contrast, take the owner of our local Lucky’s coffee shop, Deb Shinnlinger. Outside of the Upper Valley, not many people know her, but she’s a fascinating woman with a story to tell that you’ll want to hear. And doing the podcast in her café was perfect for someone who is fanatical about great coffee, like me! 

How do you put an episode together?

I do a little background research, but not much. I’ve interviewed so many people over the years in all sorts of venues that I feel confident I can rely on my own intuition. I try to treat it like a real conversation and less like an interview. A lot of times when you talk to someone in real life, the conversation is superficial. You talk about the weather or your kids. It’s not bad; it’s just the way it is. It’s unusual to really have an in-depth conversation. I try to approach it in the same way as you might when you know someone well, when you can really talk.

If you were going to interview someone famous, who would it be?  

At the top of my list would be President Obama and Michael Jordan. They’re the best in their respective fields. People who have achieved the maximum you possibly can in a field are few and far between. They are true outliers. I’d like to see if I can get them to really open up—not just sound bites and the usual talking points. Like everyone else I talk to for The Sydcast, I would want to know what makes them tick and how that translates to their personal and professional lives.

What podcasts do you listen to?

I have learned a lot about podcasting from my Tuck students. They all listen to podcasts, which didn’t exist when I was younger or in school, but they’re really taking off now. I like How I Built This, an NPR podcast hosted by Guy Raz. He does a fantastic job interviewing entrepreneurs about how they built their companies. In the political arena, I listen to The Axe Files hosted by David Axelrod, the right-hand man to President Obama when he was in office. He gets a lot of famous political players on his show.

Why have you dedicated your professional career to helping senior executives become more effective leaders?

Leadership has always interested me. I don’t think anything of importance in the world can be done without leadership. If you can be a leader, if you can energize and motivate and unleash the creativity of people around you, you can do almost anything. You are leveraging your capability to a gigantic extent. That’s why leadership is so important at Tuck. And to me personally. You cannot accomplish anything of importance without leadership skills.

What do you hope your listeners come away with?

I hope listeners will learn something about themselves by listening to my conversations with people. I want them to reflect upon their own lives and how they’ve crafted those lives, all without even knowing they’re doing it.

Click here to subscribe to The Sydcast on iTunes.