Professor Sydney Finkelstein discusses his latest book Superbosses and what superbosses do that’s so special including how they manage millennials, and where to find them in your organization. Sydney Finkelstein is the Steven Roth Professor of Management and Director of the Center for Leadership at the Tuck School of Business at Dartmouth College. He holds a Masters degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 22 books and 85 articles, including the #1 bestseller Why Smart Executives Fail. He is a Fellow of the Academy of Management and a top 25 on the global Thinkers 50 list of top management gurus. His latest bestselling book is Superbosses: How Exceptional Leaders Master the Flow of Talent, which LinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.”
Listen to the Podcast here:
Superbosses: How Exceptional Leaders Master the Flow of Talent
My guest is Sydney Finkelstein. He is the Steven Roth Professor of Management and Director of the Center for Leadership at the Tuck School of Business at Dartmouth College. He is also the author of the book Superbosses: How Exceptional Leaders Master the Flow of Talent. Sydney, thanks so much for joining me.
It’s great to be on with you, Karen.
When I met you in Thinkers 50 in London, I knew who you were. Your reputation proceeds you in a good way. I was delighted to talk with you and have a conversation with you there. I was thrilled you were going to come on the podcast here. You are the author of the bestseller, Superbosses.
I am. It came out about a year ago. It’s been a real whirlwind with the book. It touched a nerve.
What exactly is a superboss?
A superboss is a leader that creates other leaders. A superboss is someone who sees the potential in other people often before they see it themselves. A superboss is also someone that has track record of generating and regenerating talent on a continuous basis. They’re the types of people, types of leaders, that build organizations around other great talent. Unsurprisingly, they end up leading teams and organizations that have very superior performance.
What you’re saying sounds so obvious, not in a negative way, but it sounds obvious and it sounds simple. It sounds logical, and you know and I know from having been a management consultant for a long time before I was a branding strategist, what you just said sounds so easy to do, but in practice, isn’t so easy to do. Has that been your experience in researching and writing the book?
I can’t tell you how many people have told me this is the years, even before I started researching the book, “I don’t have time to take care of anyone else. I got to hit my numbers.” What they miss is so transparent. It’s so obvious, but yet so many people are missing it. If you surround yourself with great talent, the people that are good and getting better and better, how is it that you, yourself, would not get better and not accomplish more? It’s an equation that’s hard not to follow.
Do you think you have to hire people with great talent or do you think it’s possible to have people who have great potential talent and mentor them to that point? Which did you find in your research was more important, the hiring or the mentoring?
Superbosses do both and do both very well. I spend a lot of time trying to understand who they hire and how they think about that hiring process, the searching for talent process. Once people are on board and even if you inherit a team where you haven’t hired them, there’s so many things you can do to help develop them. The answer is both are critical components of what Superbosses ended up doing.
You’ve done 22 books, is that correct?
Yes, it is.
That is a first for this podcast. Congratulations. You’re making me feel like a slacker at only nine. One of your books was the bestseller, Why Smart Executives Fail. I know you found correlation to executive superbosses who succeeded by doing that. Did you find any correlation to executives who failed by not doing what you talk about?
Superbosses Book: Why Smart Executives Fail: And What You Can Learn from Their Mistakes
The Why Smart Executive Fail leaders were tough people, but they were also very smart. They had a great track record until things started to go a little bit haywire. The truth is there were some Superboss leaders that also were very tough. Larry Ellison from Oracle, very tough guy. He doesn’t fool around, but, has a tremendous success than someone who also generated so many great people around him. They’ve gone on to tremendous success. The big differentiator that I came to realize was that while both of these Why Smart Executive Fail leaders and some of the Superboss leaders are very tough and difficult and challenging, the Superboss leaders understand that to be successful, you want the world’s best talent and the best team around you. The Why Smart Executive Fail leaders, they never got that. The purpose of a team was to make you look better, was to have someone to blame if things didn’t go right, to have that musical chairs revolving doors to try to bring people in when something wasn’t going right. They didn’t appreciate the value of other people and they thought that their success, Why Smart Executive Fail leaders was due to themselves. For superbosses, while they didn’t lack from ego, they understood that winning is all about having the world’s best talent around you.
That’s an interesting distinction because often, we think of it as like if you have a big ego or you’re a strong person, that it is in a way counter to empowering other people around you to be great. What you’re saying is that the differentiator is not whether you have a big ego or you’re a strong person. It’s that knowledge that your team is what’s what is going to make this happen and empowering them is key.
That’s right, and sometimes people underestimate the importance of self-confidence. You can’t do anything without tremendous self-confidence. I don’t think I’ve ever met anyone very successful in whatever endeavor that didn’t have that powerful confidence in themselves. What that allows you to do, and this is what I saw the Superboss leaders, is that you’re not insecure. You’re not threatened by other people. As a result, you could step aside at times and make room for other people to be the center of attention, to give, to delegate, and to give people a chance to shine. That’s how you get better when you’re thrown into the ring. If you’re not self-confident, you’re a little bit worried about that because maybe that person will outshine you. Confidence is a critical component for successful leadership.
We’re talking about this in the context of work and business and corporations, but my whole life, I’ve done acting just for fun. I’ve done a lot of theater acting. I was thinking of the best actors I’ve worked with and I know are actors that allow their fellow actors to shine, that they give them their moment, that it’s not always about them. Some of the most difficult and unpleasant people I’ve worked with people are people were it’s always about them all the time, where they have to be the star all the time. I don’t think this is limited to bosses in the workplace. This is in some ways true even if you’re a person on a team.
You’re right about that. We’re talking about people. These are people that happened to be leaders of organizations and are mostly in the corporate world, although on Superbosses, I looked at a lot of people that were in all walks of life. It’s not surprising because it really is about people. What you’re also talking about something I’ve seen especially in my coaching and consulting work, which is confidence is so critical, but there’s another side to the coin, which is humility. The best leaders can do both. Someone who’s always humble, we might revere that, we might like that, but sometimes you got to step up and take charge. You have to be able to do that.
I remember reading an article in the New York Times about Stephen Curry, the great basketball player for the Golden State Warriors. His coach described him as someone who had this incredible humility about him, but he also had this rock-solid confidence that he could step up and take over a situation without any questions or any doubts about that. At the same time, apropos to your example of a great actors helping other people and letting other people shine, he was able to help that. He was able to help other people raise their game. That’s a powerful combination.
What do Superbosses do that is so special and how does it affect not only their own success but the performance of their business? Is there a particular set of skills that you found that are specific?
Superbosses do a bunch of things that are either more than your typical good leader will do and then some that are quite different. I call all of that the superboss playbook. To give you a little bit of a flavor for that, one thing that superbosses do is they have an uncompromising vision. Vision is not a new idea, but they have a compelling vision. Someone like Alice Waters, the restaurateur and chef. Her restaurant has been a pioneer in America with a farm to table local sourcing, sustainable organic food, and now it is very common. She was the pioneer in that area. She has a vision about what it means to eat and to eat well and the nature of the relationship between farmers and suppliers, the food that they create, the chefs that convert that food, and the people like us that are eating that food. You’re not going to compromise on that. At the same time, she and every other superboss have this track record and ability to unleash the creativity of the people around them.
That’s a little bit counterintuitive when you have a strong point of view and you’re not compromising, but at the same time, you’re completely open to any types of ideas that can help you fulfill that vision. The reason why that works is because you have superboss leaders that understand that they don’t have all the answers to all the problems, but they want to have all those people around them that keep coming up with new ways of approaching things. This unleashing creativity, and unsurprisingly perhaps, is one of the most compelling stories you hear from millennials. I speak to a lot of different groups. I was speaking to a group high-power millennials and they were all over this idea. They want to make a difference. They want to have an impact. When you work for a superboss leader, that’s exactly what you get. You get that opportunity, but at the same time, you’ve got to buy into this overarching vision. That’s one key element of what I call the superboss playbook, the things that they do that are different than most other leaders and most other bosses.
We have people in the audience who are solo entrepreneurs and C-Suite executives in Fortune 500 companies. We have CEOs of mid-cap companies. If I’m an entrepreneur and I don’t have a team, maybe I use people virtually or I scale up when I need to, is there a way that a solo practitioner can be a superboss?
I’ve come to realize that one of my initial focus was on a manager or a leader or an executive. The truth is that a lot of the techniques and approaches that superbosses do can be applied in almost any situation, whether it’s at work or not. Then with the colleagues, people that you might be in a cross-functional team with or in the case of entrepreneurs, people that are in your ecosystem as you start to build your company. It’s a mindset. It starts with this mindset that says, “We don’t have to do things the way things have always been done before. We are able to treat people in a way that is going to help them help them shine and fly and accelerate.”
All that stuff helps you. It could be from strong vision and then unleashing creativity. It could relate to how you develop the people around you and the opportunities that you want to give to those people, how you manage them on a one-to-one basis, and how you even teach people. Any one of us could be great teachers. All of those things are completely amenable to all sorts of situations, including an entrepreneurial one.
In an organization, where did you find the superbosses?
I focused a lot on people at the very top of organizations. That was a research strategy because they were interesting, and they would lead me down the path of learning a lot about these people. As I got into the work a little bit more, especially as I’ve done workshops and consulting around Superboss ideas, I’m finding superbosses everywhere. The problem is so two things. Number one, superbosses exists up and down an organization. I know it for my research, but I also know it because I do a book signing and people ask you to sign the book to somebody, their boss. Someone I never heard of in a company I barely knew existed, they’re just people all over the place.
That’s the first thing. The second thing is, do we know who they are? What happens if we don’t? These are tremendous assets. These are diamonds in the rough that hold the key to developing some of the strongest teams around. We don’t always know who they are because we’re either not trying to measure that or assess that. I spent a fair amount of time trying to help organizations answer that very question, “Where are superbosses? How do we find them?” Once you know who they are, you can learn from them, but you could also have them as teachers internally where you can have them be role models for other people who want to adopt some of the Superboss ideas.
Superbosses Book: Superboss leaders are very comfortable with high aspiration people. They expect that.
You’re talking about the superbosses, empowering people, and making them great. One of the groups that I have found as challenging for a lot of the people that I consult with are millennials, because they seem to work on a completely different basis than people in our age group work in. How do superboss leaders manage millennials? Do they manage them differently? If they do, how so?
Superboss leaders are very comfortable with high aspiration people. They expect that. They have a high-performance expectation. People that have high aspirations, people that want to make a difference, people that are willing to work hard and can contribute in a variety of different ways, superboss leaders seek out people like that. There’s a very big audience of millennials. If you think about it, there’s 70 million in America. It’s a crazy number.
They’re not homogenous.
They’re all over the map. If you are a millennial, I’ve heard this many times, you want to work for a superboss. The audience of millennials I was speaking to, they were asking, “How do I find one for myself? That’s exactly what I want because these leaders, they open the door for us. They give me a chance to have a seat at the table.” Having said that, the expectation for making stuff happen for performance is so high that if you can’t keep up, if you can’t do it, you can’t perform, millennial or otherwise, you’re not going to stick around for a very long time. I love that idea because you hear from a lot of CEOs and senior executives, they get a little fed up with millennials. They’re entitled. They want this, they want that. Then I talk to millennials and I see the energy and I see the capability.
With superbosses, you have a seat at the table. You’re given it even before you might in some other types of companies, but then you got to do something with that seat and you’re not going to keep that seat if you can make stuff happen. That’s fair. That’s a two-way street. You have the opportunity, but now blow through that opportunity and show me that you can do it. That’s the game that the best millennials will rise up to. The ones that can’t, that’s fine because no organization’s going to be successful with second-tier players, millennial or otherwise.
You’re going to get that seat at the table, but then you have to keep it is really key.
You got to produce. Superbosses create these high-performance cultures, and they have that expectation. You have to produce. That’s fair.
My guest is Sydney Finkelstein. He is the author of Superbosses: How Exceptional Leaders Master the Flow of Talent. LinkedIn Chairman, Reid Hoffman, calls that “The leadership guide for the networked age.” That is high praise indeed.
I had a great conversation with Reid about these ideas and it resonated with him, which was very affirming.
What do you think are the biggest disruptions going on in business today from your point of view?
Everybody talks about digital disruptions and we’ve got to start with that. What Amazon is doing in retail, affecting retail in particular, the rise of artificial intelligence, AI-enabled businesses, that’s going to change everything. It’ll lead to a necessity rescaling. McKinsey has a whole series of great studies that are being completed on what that means, what industries are going to be affected, and in what way. That’s clearly a gigantic disruption. The gig economy and how people are much more freelance than ever before changes the job of a manager. How do you manage people when you don’t necessarily have people that are your direct employees that happen to be your direct reports for periods of time? The fact that they’re all over the place and not in the same location requires all sorts of virtual techniques of management and leadership.
All those things are going on. In the context of our conversation, perhaps the biggest disruption of them all is how people think about work and their jobs and their careers. There’s no question that millennials are spearheading that approach, but I have seen time and again how other generations, I’m part of the baby boom generation which is a very big generation in and of itself, many of us watch what millennials are doing and what they’re demanding and saying, “Why am I paying my dues for fifteen years before I get that opportunity? Why did I do that in the past?” We’re seeing a disruption now in how people think about their jobs. It leads to a much more fluid job market. It leads to having most talented people move and not necessarily stay with you in the same job or in the same team or even in the same organization. That requires a different approach to management and a different approach to leadership. You can’t just be fighting it.
The most pointed way I could describe this is so many CEOs that I talk to and have talked to emphasize talent retention. Many companies have metrics on talent retention. I love great talent, I love to keep talent, but the truth is, that train has left the station. Talent retention is a very difficult thing to be trying to optimize even if we like it. Anyone who works in an organizational setting, even at a lower level, you have to realize that people are not going to be staying forever. As a result, you have to change how you manage those people. That’s a big part of what I ended up living in as well from Superboss. I consider that maybe the biggest disruption in them all.
If you think of it as a funnel, the funnel was always get good people in and then put 90% of your effort into keeping it, talent retention. One of the shifts that’s happened is the whole funnel has opened up. You need to put a lot more of your efforts and attention in having a continuing stream of good people and then a lot more of your focus and attention in developing good people because good people aren’t going to stay as long. They’re going to leave just by the nature of the way work is changing.
There’s a really important implication which is if I know that I’ve got some great woman or man on my team, and then they’re going to stay maybe two or three years, but I wouldn’t mind keeping five or six years, how am I going to do that? Yes, developing them, but also coming up with a game plan on what they want and how they think about their own career. What are their aspirations? Then you can reverse engineer that and say, “Here’s how I can help you fulfill those career aspirations. You’re going to do this job and that job, but I’m going to be open to moving you here. At some point, I may even be willing to help you get another job somewhere else,” which is ultra-radical thinking in traditional organizations. That’s what you got to do. That’s going to require a different mindset among a lot of managers and leaders.
It is literally one of the biggest challenges companies and leaders are going to face in the next decade.
Think about what happens if you don’t do that. You’re going to lose people anyways because you cannot force people to work for you. When I was describing this type of idea to a CEO, he said to me, “Why would I want to let my best people go? Why would I want to do that?” It’s so telling, those words, “Let my best people go.” As if any one of us have a controller over those who work for us. It doesn’t work that way. Especially today when you have a mindset of a freelance and gig economy and the type of movement we’re talking about, you can’t force people to work for you. As soon as you realize that, it’s time to wake up and say, “How can I be strategic about that? How can I think about that? How can I manage the flow of talent into, through and often out of my organization?” It turns out when you’re good at that, you’re going to have a value proposition for incoming talent that’s going to make you become a talent magnet. People are going to want to work for you because they know that if they spent two, four, five, eight years working for Karen, working for Sydney, working for whomever, that’s going to accelerate their careers. That’s what you got to do.
There’s a scene in the movie, The Devil Wears Prada, where one of the actresses is saying about Meryl Streep, who’s paying this famous head of a fashion magazine, “If work for her for two years as her assistant, I can go out and get a job in any publication.” They’re literally talking about that’s the reason people come to work for this woman. If you do it for two year and you tough it out, you can then make your career. It’s going to be a little bit like that. It’s going to be seen as a stepping stone and a place to go to your next place, and there’s nothing wrong with that. We have to get into that mindset rather than in the mindset that we’re habituated to, which is people stay for 30 or 40 years.
I’ve also observed an interesting positive side effect of this, which is when you do all the things that these superboss leaders do to develop talents, to support people, and to unleash creativity, you create this incredible loyalty. It’s paradoxical because they intent of people is to move on and keep advancing their career, but they often end up staying longer than they otherwise would have because of all the great things that their boss is doing for them and with them.
There are three themes that are very important to me that I like to ask each guest about. The first theme is what I call the joy of missing out. You know how everybody has a fear of missing out? We ought to practice the joy of missing out. One of the things I want to know is what is it that you think people have a fear of missing out on regarding leadership that in your opinion they shouldn’t? What should we have a joy of missing out on in regard to the larger leadership conversation?
A lot of leaders want to advance because they like the power and they like the stuff that comes with their position. In the old days, it was very common to think about it in terms of corner office, a private parking spot, access to the executive dining room, and things like that. I say the old days facetiously, because it still exists today in many companies, which is a little bit crazy when you think about the power of breaking down boundaries. You’re much better off without any of that. You’re much better off doing what some of the superboss leaders did, which is sit down in the cafeteria with people that are two or three rugs below you in the hierarchy and just chat with them.
Michael Miles was the CEO of Kraft in their hay day in the ‘80s. Under his leadership, many people and many of his protégés ended up becoming CEO of companies like Mattel and Gillette and CBS, Marks & Spencer, really incredible. He used to park in the distant parking lot to take the shuttle bus every day, even though he didn’t have to. He’d take the shuttle bus to talk to people casually as he was coming in. He looked for every opportunity to talk to people. The joy of missing out or the fear of missing out is you don’t want to isolate yourself. The higher up you go, very often organizations do this because of prestige or money or because of who knows what. The more you isolate yourself, the less you get to know what’s going on and the less fun it is.
Another theme of this podcast is what I call living beyond the script. There’s this prevailing script as it relates to leadership. I’d love to know your point of view on how do you think we can go beyond the prevailing script that exists today about what leadership is and what effective leadership is.
The view of leadership has changed over time and it’s very diverse. There are a lot of different approaches. There’s the vestiges of the Jack Welsh School, which is all about performance and pushing people hard, but there’s also a humanistic school. It maybe not quite as big as I personally like, but it’s still there. Helping other people improve their lives and their careers is one part of it. The second part of it is something that I’m seeing a trend towards that is different than in the past, which is in terms of public policy and speaking out about issues of the day. More and more CEOs are doing exactly that and part of it might be a reflection of the presidential administration in the US.
Tim Cook of Apple is one of the most prestigious CEOs in the country, speaking out on things like gay rights, speaking out on things like immigration, and the need for open immigration. Previously, a lot of these conversations happen behind closed doors, but now there’s more open conversation and openly speaking out about this. That’s a big change and that’s a next generation type of leadership approach that I suspect will become more and more common. The reason I say that is millennials think this way and as a teacher of MBA students, average age is 28, I’ve seen over time how that mindset of these young people has shifted towards genuinely caring much more about not just the bottom line. They’re caring about that to be sure. They want to advance their careers, they want to be successful, but they’re caring about social issues, environmental issues, and human rights issues much more than ever before and that’s going to become part and parcel of what leaders are going to need to spend time doing, thinking about, and acting on.
There has been for a long time a script that if you were a CEO, you stayed out of that and you handled it privately. One of the big changes in that script is people are starting to be way more public about it. The last thing I’d like to ask everyone about is I call this the everyday artist. Every person who works, some of what they do is art and some of what they do is science. In what way do you consider yourself to be an artist in your work?
I think of myself as an entrepreneur and I haven’t used the word artist in general, but it is quite a apropos. As a researcher, I am a social scientist, and so I do very careful research where I collect a lot of data and I go through multiple stages of research with a big research team. In some ways, a lot of the research I do is all about science or social science. The differentiator for me for successful or best or most impactful research, the stuff I’ve always found to be the most interesting and most fun is around creativity and asking the right questions. It’s one of my litmus test before I started working on a big project that may become a book. I talk to people that are not in my field, they are not professors, they are not necessarily CEOs or senior executives. I tell them what I’m thinking about doing and we talk about it. I want to know whether they think it’s interesting and I try to get that feedback.
Even in that regard, I’m collecting data on a creative idea. There’s the teaching side, which I use the Socratic method. It’s very much of a choreography in each class and there is an absolute art to it. I teach sometimes multiple sections of the same material, the same course, and each class starts the same way and ends the same way but through the 90 or the 88 minutes in between, it goes through a very different path. Being able to be flexible and adaptable and really immerse yourself in that process of creation is one of the most fun things about what I do. I don’t know if that’s being the artist or not, but it’s certainly a much more organic way of thinking about doing what I do.
Superbosses Book: Always do more than what other people expect of you. Create things differently, do your job, always look to extend and stretch.
You were designated one of the top 25 global thinkers on management gurus by Thinkers 50. How does that feel? How do you think you get to a place like that? What’s your secret sauce of getting to a place like that?
It’s always good to be recognized by peers and others, so you can’t pretend otherwise. There’s a reason why people show up at the Academy Awards and the Emmy’s and the Golden Globes. We are people, we all have egos. I plead guilty, I liked it. There are a lot of paths to being recognized in whatever your field is. I never mind being recognized but there are a lot of paths to being one of the best in your field. What is common is number one, always doing more than what other people expect of you. That might mean creating things differently, doing your job, whatever it happens to be, but always looking to extend and stretch and stretch that.
Number two, good old fashioned hard work. There is no replacement for that. I don’t consider what I do work, so that’s a beautiful thing. I love it that much, so maybe that’s the first thing I should say, find a field of endeavor or job or career track where Sunday night feels just as good as Friday night because you just love it, you love what you’re doing. I’ve been very fortunate in that regard. Then I would say, and this is critical, you have to want to do something or say something or create something that is different than what anyone else has done. Just following best practices and just doing what others have done and doing it more efficiently can lead to a very successful career and that’s okay. Maybe there are a bunch of CEOs that have done that and that’s moved up step-by-step.
If you want to be noted, if you want to have that long-term impact in your field, you want to be able to create. You have to be interested in and have the ability to create something brand new, whether that’s a new way of thinking, in my field, whether that’s a book with new ideas, whether it’s something more artistic, or even in a traditional business setting, whether it’s coming up with an innovative, new approach to competing in your marketplace. Finally, if you’re an entrepreneur, that’s what you do. You’re creating something. Just doing what everyone else has done is boring. If you don’t have that mindset, it would be very difficult to end up getting to the top of any of any field that you’re in.
It’s the art, not the science.
In most fields, most good people have the toolbox. They all know how to do the basic stuff and maybe more than just the basic stuff. The people that differentiate are the ones that are able to think creatively, think entrepreneurially, and have this skill set that I would say is one part being analytical and being able to drill down to understand what are the most important concerns. At the same time, have this creative or entrepreneurial side that allows you to come up with a novel approach to whatever that critical issue is. Those jewels skills are not evenly distributed in the world.
I was talking with Melissa Schilling, who came out with a book, Quirky, about innovators. What she found when she looked at Steve Jobs and all of these various innovators was very similar to what you’re saying, which is these people not only have a vision, but they absolutely think and are willing to do things differently. They are not just following that standard script, and that was consistent with every innovator she found.
I’m not surprised by that. Melissa’s book is great, by the way. That’s exactly right. It’s very consistent with my own experiences as well.
Sydney, thank you so much for the time to be on the podcast.
Karen, what a great conversation. You put me on my toes.
Thank you. My guest has been Steve Finkelstein. He is the Director of the Center for Leadership at the Tuck School of Business at Dartmouth College. He is also the author of Superbosses: How Exceptional Leaders Master the Flow of Talent.