Chris Russell Authors

Sydney Finkelstein And The Superboss Playbook

April 20, 2016

Sydney Finkelstein, author of Superbosses, explains how to master the art of handling talent

Throughout our careers, each of us will encounter a wide range of management styles, with mixed results. But what is it that distinguishes a regular boss from a truly great boss? Why is it that some help us to reach new heights, while others can make us feel constrained in our abilities?

These are deceptively simple questions with many possible, and much more complex, answers, the latest of which comes from Sydney Finkelstein, Steven Roth Professor of Management at Dartmouth College’s Tuck School of Business, in his new book Superbosses: How Exceptional Leaders Master the Flow of Talent. Taking as his guide a range of figures from disparate industries, including everyone from the jazz musician Miles Davis to newspaper editor Gene Roberts, Finkelstein examines the key traits of those who have spawned extensive networks of talent, the titular superbosses, and ultimately brought greater success to themselves as a result.

Sydney Finkelstein, professor and author of Superbosses
Sydney Finkelstein, professor and author of Superbosses

For Finkelstein, the lessons to be taken from these extraordinary leaders represents a kind of revolution, and a sorely needed one at that: “There’s innovation in so many parts of business and organizational life, and the innovation in the world of talent I think has lagged behind.”

In this interview, Finkelstein sets out some of the key lessons from the superboss playbook.

Q. Why do you think it is that some bosses, unlike the superbosses of your book, overlook the importance of talent?

A. I find that very often, especially in modern business with all the pressures that exist, many bosses feel overwhelming pressure to hit the numbers, to accomplish what they need to accomplish, and they just kind of plough through people to try to get there. And so in a way it’s a very short-term way to think about the world because if you just pause for a moment most people would realize you actually could accomplish so much more if you have great people around you, if you build great teams, if you energize them to be contributing. And so if you’re a much better boss, or even a superboss, you actually will be much more successful yourself. But I think a lot of people don’t get to that stage because of the incessant pressure that they’re feeling because of the modern global economy.

Q. What is it that distinguishes a superboss from a merely good boss? What do you consider to be the most important aspects?

A. Well first of all, a superboss is someone that helps their team members or others accomplish more than they ever thought possible, and that’s a pretty high bar compared to how most even good bosses think about it. And so the difference to me is twofold.

One, compared to a good boss, a superboss is more intense and does more of all the good things that a good boss does like mentoring, respect, spending time [with employees] and motivation. They go deeper and they go further into that.

And then secondly, a superboss does some things that most good bosses don’t actually do, and specifically I’m thinking of this almost apprenticeship type of approach to managing people that I talk about in the book. Even though apprenticeships have been around for centuries, very few think about their job as the master and the apprentice, someone that they should be working so closely with, where your job is very much about teaching, so they seldom do that.

I think another thing most good bosses don’t realize that superbosses do is kind of the mixed sense of talent retention. I’d say if we surveyed most bosses in general, but particularly good bosses, they’d say, “Well, I want to hold on to my best talent, I want to hold on to them as long as I possibly can.” Of course that is understandable and in a way it makes sense, but what superbosses understand as well is that sometimes some of those best people are going to move on, they’re going to want some huge opportunity, they’re going to want to run the show, they’re going to want to be the boss or they’re going to want your job, and if that’s the case you have to decide are you better off helping them get to where they want to in their career or not, because it’s going to happen anyways. So as soon as you realize that’s going to happen and then you think about the upside to helping other people accomplish more by moving on, in fact even helping them get other jobs, certainly being supportive when the time comes if they want to go, you get into this whole discussion that I had in the book about networks and the power of networks and how that can continue to pay dividends for the superboss.

Q. As I was reading the book one thing I thought was a kind of underlying element to it was the vision of superbosses, and how this feeds into their approach towards motivation, innovation and hiring; it’s something deeper that kind of guides these things. To what extent would you say vision is a key aspect of a superboss?

A. I think vision is critical, but I think it’s important to have a better sense of what that word means because that’s a word that’s thrown around in business all the time and everybody talks about vision. I think in superboss world, vision means that anyone who is a leader of a team, and I’m not just talking about CEOs or some of the famous people that are in the book, but anyone who has a team should have a vision of what they want to accomplish and what it is that is possible because that is going to help motivate people.

The second thing I would say about vision is superbosses are very, very clear on what it is they want to accomplish. I’ve often thought in doing this research that for most of these superbosses they would have kept on doing what they were doing even if it didn’t make them any money. Obviously many of them are wealthy to extraordinarily wealthy, but I feel like that was so central to their view of the world that they would keep on doing it and they weren’t doing it because it was going to make them a lot of money—they weren’t going to turn down that money to be sure, but that wasn’t the prime motivation. And that’s a really powerful vision, and it does play out—it does play out in kind of their open mindedness to doing anything and everything that they possibly can to fulfill and even exceed that vision, and that requires you of course to have great talent and motivated talent, but specifically to the innovation point it calls for a leader who is willing to unleash the talent, the creative talents of people around her or around him and not be afraid of that, which many leaders of course are. And that’s because again vision is really primary and they’re open to any kind of cool ideas anyone can come up with that can help them get there.

Q. How can people begin to implement the superboss playbook, as you call it, in their workplace in the face of certain constraints or limitations? Perhaps they’re in a company that has a very rigid structure or perhaps it’s more just about the practical considerations of drawing in talent.

A. There’s no question that there are constraints that everyone faces and it’s even true for some of the CEOs, maybe all of the CEOs, certainly of publically traded companies with the pressure of quarterly earnings and the need to justify very high compensation and what have you. But bringing this back to the wider audience, there’s certain things you can’t fix either because of internal cultural things or these broader economic or climate issues, but there is actually a lot that you do have some leeway on.

So for example if you look at identifying and finding great talent, two or three of the things that are part of the superboss playbook in this regard could be applied by anyone. For example, you don’t have to follow the traditional model of just having a job description and then doing a search and checking all the boxes to see who has more of the criteria than anyone else. You could be open to and, I call it a talent spotter, always be on the lookout for great talent. You can kind of internalize that so you’re always thinking about that—you could be anywhere, and you just see someone who’s got something. Either they’re underemployed, or they haven’t had the opportunity, or nobody came to them with this, or they might be ready for a change, and you strike up a conversation, you learn about them and then you’ve got to be willing to take a bit of a chance sometimes in hiring someone. And even where there are constraints because of employment laws, so you don’t want to hire someone because it’s hard to fire somebody, which is true in Europe in particular, well you don’t have to hire them, you can bring them in as a contractor, as an independent agent so to speak. There are ways around all kinds of things.

Also with respect to talent it’s not just about not becoming beholden to the job description or being a talent spotter, but with this shift to motivation it is absolutely the case that any manager that has people working for them could make a difference. You look at some of the things that superbosses do and they have very high expectations and they raise the bar, they create a very performance-oriented culture. These are good things to do and then they add this other element that I think is critical and that is a big differentiator from many other, say, more typical companies, and that is how they inspire people. They infuse their people with confidence, they help people see and believe that they are actually the ones that can accomplish these great goals. These are things where there is no one that can tell you you’re not allowed to do that. In fact, most companies would say that would be great if you can pull that off.

One other thing I’d say is that while superbosses sure sound pretty impressive, and they are, you want to avoid becoming intimidated, believing you can’t do that. You don’t have to do everything they’ve done over a career in one week—pick and choose. Go through the various chapters and there are different ideas—pick one or two that you think could work in your environment, your world, and test them out and try them and then expand from there.

Q. One of the things you mention briefly in the book is that you think the superboss playbook is particularly well suited to managing millennials. Why exactly do you think that is?

A. I didn’t think anything about it [to begin with], but over time it started to occur to me, and then I started to test it out in seminars and when talking to students—my students are 27, 28 on average, so that’s right in the center of the millennial generation. One, millennials, maybe more so than historically with previous generations, are looking for engaging work, work where they can have an impact. And speaking myself as a baby boomer it’s not that we didn’t want that, but I think we were more of the sense that well eventually you get there but you’ve got to pay some dues, and I think millennials maybe have a shorter time horizon to accomplishing that goal, and by the way I think the world of technology is one of the reasons why they have that time horizon—the speed of everything is just accelerated incredibly—and so superbosses do create an environment where work becomes exciting and energizing and superbosses trying to accomplish big things, and they expect everyone on their team to be a player, to be creative, to be innovative. And so that plays very closely to this idea of employee engagement and what millennials really want. More broadly by the way, employee engagement as you know is one of the key metrics every company is looking for and they want to increase it and I think the superboss playbook is going to be hugely important in accelerating or improving that employee engagement.

A second point is, maybe most fundamentally I suppose, millennials are generally thinking—I hesitate a little bit because it’s a gigantic generation, there’s a lot of variation—be that as it may, with that caveat, millennials are not thinking about working somewhere for 25 years—they are much more likely to be thinking about shorter time horizons, and so they fit into this new model of thinking about talent retention in a different way that superbosses spearheaded. Millennials are more likely to say after one year, two years, five years they’re done and they want to move on to a new challenge. This is going to be more common and with the superboss approach to understanding that that’s not just occasionally going to happen but it’s perfectly okay and that we can take advantage of that, we can be strategic in managing the flow of talent, which is the subtitle of the book after all.

Q. A lot of the superboss figures you cite are extraordinary individuals, they’re idiosyncratic in their own ways and a lot of their own unique processes of managing rely on intuition and whatnot. So given those things, what is it that makes you nonetheless convinced that the superboss playbook is still teachable?

A. I think that’s a core premise of the entire project, the entire book, that, in fact, everything that superbosses do can be learned, can be taught. I looked at very well-known people because that was part of the research process and of course it’s fascinating to learn more about Larry Ellisons of the world and Ralph Laurens of the world, etc., but that doesn’t mean there’s not superbosses up and down an organization, and in my case I didn’t do research on those people because they’re harder to find. But I’ll tell you what’s happened as a consequence of writing the book—you start talking to people and I’ve been talking informally with people for some time and giving a couple of presentations as well and it’s inevitable that people come up to me and say, “I had a superboss, let me tell you about her, let me tell you about him.” And it’s not this famous CEO, but it’s some boss at some stage in their career. I think it’s much more accessible and I think it’s really, really important for people to realize that, that what superbosses do is accessible to others, to anyone, and so it is teachable, it is learnable because there’s many of them out there. We just haven’t known what to look for or thought about it and nobody’s really analyzed who these people are and what they’ve done in a way that lays out the specifics of what they do and how to do it.

I’m not saying that some of these superbosses in the book, say a George Lucas, sat down and created an HR plan of how to develop talent, in fact I’m quite certain that didn’t happen, but when you study these people and you dissect what they did you actually could see that, yes, maybe they had some genius to get there, but for the rest of us that don’t have that kind of natural intuition or that genius we now have a plan, we now know of a playbook, we now know how they did it, and when you dissect that and see it in detail in a very specific case as it is in the book, well yeah you could do exactly those types of things, tailoring them to your particular situation, but you could do those things.

Q. At what point do superboss behaviors and qualities—for example their confidence or their demanding nature—run the risk of bringing about failure or poor results. Are there any sorts of limits or drawbacks to the superboss playbook do you think?

A. I think there might be and I think part of this is a fit story—they are demanding, they are challenging, they know what they want and so for some people they might just not want to work for a superboss. It might not be the right place for them because they’re not willing to have that, for whatever reason, and I’m not criticizing because different things they need in their life or want in their life or different aspirations might mean they’re just not willing to make that type of commitment and that type of dedication. Of course I think there are many, many, many more who will be willing to and are actually almost waiting for that opportunity as they’re in jobs where they’re not engaged, they’re not energized—working for a superboss is a way to turbo charge your career and get gigantic opportunity.

But not all of them are easy to work for—that varies. I have these different types that I describe (glorious bastards, iconoclasts and nurturers) and the glorious bastard type, they’re not easy to work for, there’s no question about that. The nurturers are much more supportive and they are a bit easier, but they are also not looking for just getting along or not looking for just satisfactory results—they’re looking for exceptional results, they all are. So I look at it and say this is a fit question and this is going on independent of superbosses anyways all over the world.

Q. From a superboss perspective what are the most important things to consider when it comes to the boss-employee relationship?

A. Superbosses very much customize their supervision or their interaction to individuals. And if I can just elaborate on that a little bit, I find it really remarkable if you think of the world of marketing and sales and what has happened with the internet, when we’re on Google doing something there are ads that appear. Well those are ads specifically for us because of where we’ve surfed, etc. The world of marketing has unbelievably customized opportunities, if you will, for people to buy stuff. The world of HR, the world of leadership is in the dark ages compared to that. And I know we don’t have the same level of technology—we don’t have all that data, maybe we don’t want to do that in the context of managing people—but nonetheless we just don’t customize nearly as much. So for what should superbosses do working with employees, I think customization is an important factor. And that’s day-to-day and how you’re working with them, but also with respect to thinking about their career and their career track, again, managing the flow.

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