Fearless - Ep 10: "The Psychoanalyst" - Kerry Sulkowicz

"The Psychoanalyst"

"The culture of an organization emanates directly from the personality and values of the person at the top."

Unlocking creativity requires celebrating uncertainty and embracing risk. Most businesses aren't designed that way. Nor are most human beings. 

Instead, we stop ourselves, unconsciously and consciously. We act against our own self interest, willingly and unwillingly. We are hesitant, we are anxious, and very often - far more often than we realize or are prepared to admit - we are afraid.

Leading a successful business requires we confront our own frailties at the very same time that we are grappling with the multi-faceted threats to modern businesses.

Kerry Sulkowicz is a leadership confidant, advising the CEOs and boards of some of the world’s largest and most powerful corporations.

He is also a psychiatrist and psychoanalyst. 

Kerry joins me to talk about the very human challenges that leaders face, the mistakes that most leaders make when stepping into new roles and the deeper human impulses that exist in all of us.

Three Takeaways

  • A willingness to look at a situation from somebody else's perspective and to take time to reflect on that before making a final judgment.

  • Listen. Listening is a learned skill, and it is a foundation of leadership.

  • Generosity. The willingness to invest in others when you are the leader. Be conscious that there is a fine line between generosity and indulgence.



Episode 10: Kerry Sulkowicz


Charles Day:                         Hello. You're listening to Fearless, where we explore the art and science of leading creativity, an unpredictable, amorphous, and invaluable resource critical to every modern business. Each week we talk to leaders of the world's most disruptive companies, how they're jumping into the fire, crossing the chasm, and blowing up the status quo, leaders who have mastered the art of turning the impossible into the profitable. Stay tuned, because in the next half hour anything could happen.

Hello. Welcome to this episode of Fearless. I'm in Canne this week, at the Annual Festival of Creativity, which is a week long relentless, hopeful exercise in the exploration of creativity, and possibility, and humanity, and technology. It really is one of the most provocative experiences I think that it's possible to have actually on this planet, a real collection of people from a very wide array and diverse set of backgrounds, and skills, and perspectives. There's a lot of things that are coming out of this week. In one of the earlier episodes of Fearless, when I talked to Jim Stengel, I brought up the fact that at Canne last year I had seen and heard a number of people talking about whether purpose was in fact now passe, as though purpose can be a thing that is passe, that it could ever be a trend. What I think has been encouraging this week is to see a number of conversations talking again about purpose with real intent, and real commitment, and perhaps even at a higher level of consciousness and understanding, which I think is essential actually to the future of businesses and to brands.

This week is really about the power of creative expression in so many different ways. There was a session the other day that Susan Credle, also one of my guests a few weeks ago, from FCB, put on when she interviewed Savion Glover, the world renowned, perhaps modern definition of tap dancing, using his artistry in real time on the stage to show that brands that have clearly defined voices and points of view can be expressed in any medium, including that of tap, and that session was just an extraordinarily uplifting, powerful representation of the unpredictability and get out of your seat, uplifting possibilities of creativity. It was powerful, and brave, and confident, and I think anybody who was there will never forget it.

We've also had seen and been part of a lot of conversations around diversity and gender equality, which our tremendous issues in the creative industries, across the entire breadth of the creative industries. Madonna Badger, who you will hear on a future episode, is here again this year, inspiring and leading a movement against the objectification of women and raising people's consciousness and awareness of it, but also making practical, physical steps towards eliminating it, and certainly reducing it, and hopefully ultimately eliminating it from the role of marketing and advertising. There was a session with Colleen DeCourcy, who I think you will also hear on this show at some point in the next few weeks, talking about how technologies, like Airbnb and Facebook, have the ability to build community in the digital age that unleashes human possibility and human connections in a different way.

We saw the mentalist and the magician, Keith Barry, showing how brands can connect through the power of the mind, and I had the chance to meet Keith in person, very much up close. A small group of us stood around one night for about an hour while he completely mesmerized us, so the power of the mind to connect with the mind, to fool with the mind. It depends on your interpretation, but we've had a lot of conversations here around self-doubt and self-worth on the various stages and in the various corners of Canne. I've personally spent a lot of time this week talking about fearless leadership, both on the stage and away from the [inaudible 00:04:23]. Running through all of these is the power, and potential, and the limitations, which are often self-imposed, of the human mind. What should we do? What can we do? What do we want to do?

I think in many ways and on most occasions the last of these questions, what do we want to do, is the most important and the most challenging. We are our own worst enemies is a cliché, and for a reason. I think we stop ourselves, north unconsciously and sometimes consciously. We act against our own self-interests I think willingly and, again, often unwillingly. We're often hesitant. We can be anxious. I think very often, far more often than we realize or are prepared to admit, we're afraid. This week's a journey I think for many of us who are here for the discovery of new ideas and new ways to look at the world and also to discover ourselves.

Cannes is a challenge to our stamina, and to our definition of what's possible, and to our definition of self. It's eye opening. It's mind bending. It's absolutely exhausting, so forgive me if I'm stumbling occasionally here. Nobody who comes gets very much sleep, because I think we are conscious of the possibilities that exist by being out and engaged, and so we try to do that a lot. It tends to break down our guards, and it builds up our hopes, and we start to see things in new ways. It's also emotional. I think, as I had looked at this and reflected on this in a different way this year, in large part I think because the podcast is forcing me to do so or encouraging me to do so, at the very least. In some ways I think Canne is the definition of what it means to be human.

My guest on the show this week is Kerry Sulkowicz. Kerry is a leadership confidant. He advises the CEOs and the boards of some of the largest and most powerful corporations. He's also a psychiatrist and a psychoanalyst. As someone once described him, he is a doctor of the head. Kerry joined me a couple of weeks ago, and we talked about the really human challenges that leaders face, the mistakes that most leaders make when they step into new roles, and he also talked about the deeper human impulses that exist within all of us.

Charles Day:                      Kerry, welcome. Thanks for being here today.

Kerry Sulkowicz:                Thanks for having me, Charles.

Charles Day:                         Your background I've always found very fascinating. You are a trained and were for a long time a practicing psychiatrist, and then, at least the way you tell it, almost over night or certainly very quickly you became what has been described, in the New York Times no less, as a business shrink. Tell us about how that transition happened and what, from your perspective, being a business shrink means. I know it's not a phrase you would use, but it has been applied.

Kerry Sulkowicz:                 Yeah. It's not how I would describe myself, Charles, although I'm sure I've been called worse things than that. I'm also trained as a psychoanalyst in addition to being a psychiatrist. I mention that only because in some ways it's more the psychoanalytic part of my training and experience that informs my work today more than the psychiatric part. Psychiatrists are thought of, appropriately, as really looking for mental illness and treating it, whereas psychoanalysts, while they do that, I think are more interested in understanding the deeper underpinnings of human feeling and behavior and applying it in a way to help individuals of all kinds live more fulfilling lives. It's that part that applies more to my work today.

I stumbled into doing what I do now. It wasn't part of a grand plan. I was in full time private practice for about five or six years and loved some aspects of it, which were helping people, I still like that, and the intellectual underpinnings of it I think were also stimulating and remain so. The part of clinical practice that was somewhat frustrating to me, or at least wasn't a good match for my temperament, was sitting in an office, albeit a nice office, all day, and seeing one patient after another, and feeling somewhat stuck in the rigor of that kind of daily routine. I was hungry I think for an opportunity that then I really stumbled into at a cocktail party when I was talking to an entrepreneur of an internet start up back in the mid 90's. I sometimes describe it as one of the occupational hazards of being a shrink, to use that phrase, that at cocktail parties people, especially after a drink or two, unburden themselves, which I have always enjoyed, because I really do like listening to people's stories, getting to know them.

This man, who has since become a dear friend, was talking to me about his struggles as a first time CEO, having started a business with two partners, that they had left together from a big firms. At the end of the conversation in which I mainly listened and said a few things, he asked me when I would be able to start advising him and his company in his capacity as a CEO. Truth be told, my initial answer was I didn't know what to say, and so I told him I thought he was out of his mind, which is a dangerous thing for a psychiatrist to say to somebody, but he actually appreciated the candor. It turns out that was part of the appeal, which is that as a CEO, he, like all CEOs that I've come to know over the last 22 years, are inherently isolated and need somebody to talk to. The combination of needing somebody to talk to and also bringing a clinical, psychological perspective to bear on their on their challenges as leaders turned out to be the basis of what became my career.

Charles Day:                         As you now focus on this sort of second career, you are I know working with a lot of very powerful, influential CEOs and their boards, and you describe yourself as a confidant. What form does most of your work take?

Kerry Sulkowicz:                 Well, you know, I like the term confidant better than corporate shrink, because that really is what I do. I have spent the last 22 years being a confidant or a sounding board to leaders of organizations and their boards. The client is always the organization, as opposed to the CEO or any other individual in it, because I like the ability to immerse myself in the senior team and the board, the culture of the organization, getting to really know the business, the work of the organization. I really serve as a sounding board on the soft stuff, on the people, the interactions amongst them, certainly a lot of time focused on the challenges that the leader faces, including the emotional challenges of leading an organization. Then I get involved in the psychology of governance as well, the dynamics of the board room, the interaction between the board and the CEO. It's really a focus on people and culture, Charles.

Charles Day:                         One of the things that I think is often overlooked or maybe misunderstood is the role of a leader. You know, I think we all have just banded the term around, and organizations look at leadership as the thing that has to happen at the very top of the organization. Somebody has to do it, but I don't think there's often enough thought given to what does that role actually entail. From your perspective, why are leaders important. What is it that makes them essential to an organization, other than the obvious, somebody has to make a decision on a day to day basis?

Kerry Sulkowicz:                 There's certainly a lot more to it than that, although that is clearly a part of it. You know, look, leadership matters. These days, in the state of our world being what it is, one needs look no further than the White House to see the effect of a leader on a vast group of people, on the country in this case. I don't think there's been a more dramatic example of the dramatic and almost immediate effect of a change in leadership on the way it feels to be a part of this country, no matter what your political beliefs are. That is certainly true in the kinds of organizations that I advise, which for the most part are fairly large, for profit companies, many of them publicly traded, some privately held.

The leader does a lot more than make decisions. The leaders sets the tone of the organization. The leader sets the culture, and in many ways the culture of an organization emanates directly from the personality and from the values of the person at the top. You see this in a most pronounced way in organizations that are led by the founder, but I think it's true in all organizations, whether they're founder led or run by the 10th professional executive in a row. They do have a profound impact on what it feels like to both be inside the organization as an employee, as well as what it feels like to interact with it from the outside, whether that's as a customer, or a vendor, or anyone else on the outside. The leader sets the tone, and values play a big part in that. The leader determines the course of the organization, in terms of its strategy and how it tries to execute on it. You can't overstate the impact that a leader has on really every aspect of an organization.

Charles Day:                         Values are such an important topic, and I think, again, it's one that's either misunderstood or sort of misrepresented. When you're working with a leader through the lens of helping them to articulate their values, what's your focus? How do you help them extract what my value should be as a leader?

Kerry Sulkowicz:                 Well, to some degree they are going to do it, no matter if they're deliberate about it or not, because we all have values. We all have habitual ways of making decisions, and they're based on something. A leader is going to affect this parameter of an organizational life regardless. What I try to do is to make them more conscious about it, more deliberate about it, to actually step back and think about it, which sounds like a simple minded thing to say, but you'd be surprised how many don't really think about it or at least put it off until later. "We'll get to that later. We've got more urgent things to deal with now," is what some of them say, and I would respectfully disagree. There's really nothing more important than setting the values and modeling them.

Leaders are closely scrutinized, as you know, Charles. We talk about that all the time, not to make leaders paranoid about being watched, but just to recognize that every, not only word that they utter, but every behavior that they make is going to be closely watched and on some level emulated. That's one of the ways that values get disseminated through the organization.

Charles Day:                         I remember I lived through that reality myself when I was running a business, and one of our employees walked up to me in hallway one day, and she said, "I have a question about this client. What do you think I should do?" She described the situation, and I said, "Well, I think you should do this," and she looks at me quizzically. I said, "Doesn't that make sense?" She said, "No. It makes total sense. It's exactly the opposite of what you told me to do a year ago." I said, "You remember what I told you to do a year ago?" She looked at me like I was crazy, and she said, "Absolutely." In that moment I realized we are being looked at through a different lens. Like it or not, there's a different responsibility that comes with occupying the role of being a leader in any organization.

I think you and I in our work have both seen this a lot, right, that leaders sort of will happily throw a quick comment over their shoulder as the walk out of a room, not realizing they've just set off a stick of dynamite in the conference room behind them. Everyone's going, "What does that mean?", and, "Oh my god." I think, to your point, this sort of acknowledgement of, "Yes. I am the leader, and I have to take that seriously," is really important, and a lot of people walk into this I think with a lack of awareness of that. When you start to work with somebody for the first time, what's your first point of reference? What are you looking at and for?

Kerry Sulkowicz:                 Well, again, when I start to work with someone, it's really an organization. The someone that represents it first is typically the CEO.

Charles Day:                         Do you most often get called by the organization or the individual?

Kerry Sulkowicz:                 Usually the individual. Probably most of my referrals come from either current or former CEOs that I've worked with or members of boards. I like to do a lot of work with boards, and directors tend to sit on multiple boards, and so that's usually the route in.

Charles Day:                         What's their request of you? What are they looking for?

Kerry Sulkowicz:                 It varies. There's a certain self-selection, I should say, in terms of the kinds of clients that come my way. The really sort of horrid, extremely narcicisstic CEOs who don't think they need help from anyone, because they have all the answers, they're not calling me, although I do tend to meet them when they're being fired by their board. That's when I sort of meet them, on their way out the door. I think if there is a typical, and the clients that I work with, that I've been so blessed really, it's quite a diverse group, but I think if they have one thing in common, these companies and their CEOs recognize that the people are the most important aspect of their organization.

The leaders recognize that it's lonely, and that it's helpful to have somebody to talk to, and that they acknowledge that they don't have all the answers, because they're dealing with so much uncertainty all the time. They have a modicum of self-awareness, at the very least, that it might be useful to have a coach, to use that overused term, which I don't really like, but it often comes up in that context. When I dive into working with a client, what I'm really interested in doing is just learning. I do certainly a lot more listening than I'm doing in this conversation I'm having with you, Charles.

I really want to get to know the individuals who are responsible for leading the organization, starting with the CEO. Who is he or she as a human being, not just as an executive? I want to get some of the fabric of their lives. I also want to understand something deeply about the business, and so I spend a lot of time trying to understand it, walking around, learning about the products or services that they're selling. It's an immersive process. There's no formula for it, but the more I can know and the more people that I can know, the more helpful I can be.

Charles Day:                         Yeah. It's an interesting evolution and journey to go to, without obviously having your background and your expertise, from a psychoanalytic standpoint, it struck me very early on, as I started to give advice to people, that understanding their personal story is such an essential part of this work, because you have to know where they've come from and what their childhood was like, at least through some perspective.

Kerry Sulkowicz:                 Yeah. No. That's right, and you don't always get that personal story. It's not as though we have to get through that in the first meeting. Sometimes it takes months for that to emerge in a more naturalistic way, which is completely fine. In fact, it's often better that way. But, yes. Those personal stories inform who they are as people first and as leaders.

Charles Day:                         We were chatting a few weeks ago, and you posited a theory to me, which I have been struck by ever since. We have talked about this a little bit in the past, but I'd love you to talk about it more today. You said that in your view almost every leader, or maybe even every leader, is working to overcome some sort of childhood trauma, some sort of event that happened to them in their past.

Kerry Sulkowicz:                 Yeah. I would say that the best, most effective leaders that I've known, and I tend to have a bit of a bias there, in that I tend to see some of the most effective leaders as the more entrepreneur kinds of leaders, and leadership is forged in the cauldron of life experience and biology. It's not something that one takes a good course at Harvard Business School in and then you become a great leader. As a student of leadership and trying to be something of a leader myself, I look inwards as well. We all have our stories, as you just said. I couldn't agree more, and some of those stories are painful. They involve overcoming ... One never fully overcomes adversity, but adapting in some ways to early adversity. I'm always reluctant to make these generalizations. Let me just preface to this that any generalization is of course not always applicable.

With that caveat, I'd say that I've seen, in some of the great leaders that I have worked with, a particular form of early childhood loss, whether it's the loss of a parent, either entirely through death, or through parental divorce, or the mental illness or physical illness of a parent. That's not uncommon of course. It's tragic, but not uncommon. What is uncommon is the particular adaptation that some of these people make in their early lives, and that is that they respond to these early losses by stepping into a kind of precocious parental role and becoming the woman or the man of the house, so to speak, and in a sense are drawn into being leaders of their family well before they're supposed to, if there is such a thing as supposed to. Some of those people go on to be remarkable leaders. Not surprisingly, there's always a down side, because these events early on leave scars. As extraordinary as these people can be as leaders, they also have their vulnerabilities that can be traced back to the very same early traumas.

Charles Day:                         This podcast, as you know, is called Fearless, and I've frequently been struck by, both in my own life and getting to know a lot of other leaders as well, that fear plays a big part in how we show up. It's not always immediately obvious, but I feel like we're always fighting against some sort of inhibition, some sort of hesitation, some sort of anxiety. Do you see the same thing?

Kerry Sulkowicz:                 Yeah. I do. I got to say I love the title of your podcast, Fearless, because it's aspirational, because in my experience there's no such thing as really fearless. Right? We all have our fears. None of us are fearless, but it's how we try to adapt to them, what we do with that fear. We can be paralyzed by it, crippled by it. That's obvious a problem for leaders, much less anyone else, but yeah. We all have our fears. We're all trying to overcome something. I think if we can acknowledge that kind of humanity that drives us, we're better off for it.

Charles Day:                         In your experience, how do people overcome their fears? What are the right approaches? What kind of things can people do to get out of their own way?

Kerry Sulkowicz:                 Well, you know, there's no formula for this of course either, but one of the things I would say in response to that is that it helps to acknowledge that one is afraid, and I would start with that. Start with some self-awareness. That's one. The other is to acknowledge that one never fully masters those fears, but one can try. I think sometimes what we do with our lives, particularly the things that we're passionate about, if we really look deeply into it, involve an attempt to master those fears. You know, starting a business involves mastering all sorts of fears, including the fear of the unknown, the fear of one's incompetence, the fear of trying to influence other people. Sometimes we may have been unduly influenced by others, and we turn that into something much more positive by influencing others, hopefully in a benevolent and constructive way. We could talk for days about the various permutations of ways to master our fears, but I think starting with an acknowledgement of it is helpful.

Charles Day:                         The fear of incompetence, as you just describe as sort of imposter syndrome we might say, is obviously prevalent in a great many people, maybe not in everybody. You'd have more insight into that than I do, but that shows up a lot. I see that showing up a lot. When you feel that, or when you sense that, or when you learn that about a leader, how do you help them go about addressing that? Because, typically if they've reached that point of success where you or I am working with them or they're at the top of their company, they have something pretty substantive to offer a that point.

Kerry Sulkowicz:                 Absolutely. One of the first things that I do when I hear that, and you're right, it's not uncommon at all, is to normalize it, because not only do some people feel like they're imposters and incompetent when they have the top job, they're ashamed of that feeling, and they're afraid that they'll be discovered. It turns out that there's not much to discover. It's actually quite normal to have it. I remember when I was starting my own consultancy, and I've been fortunate along the way. It's worked out pretty well, and people will sometimes ask, you know, "How did you come up with this idea? It's really great." The truth is I didn't discover anything. I sort of stumbled into it blindly, by the seat of my pants, not having a clue what I was doing, and I'm still learning.

Charles Day:                         Yeah. It's interesting. I very much came to it the same way. People kept asking me for advice, and I kept saying to myself, "I'm not qualified to do this. Who am I to tell them, these people, what to do?" I think it was Chris, my wife, who finally said, "How badly could you screw somebody up? What's the worst you could do if you just said yes for a while?" Yeah. I think part of it is actually overcoming your own emotion, and your own hesitation, and your own fear and saying, "Let's see what's possible here?" I mean, amazing things happen when you open yourselves up to that journey. As you look at the characteristics of the most successful leaders that you've encountered, either personally or through observation, what do you see as the characteristics that stand out to you?

Kerry Sulkowicz:                 Well, there's so many. I resist trying to come up with a comprehensive list, because somebody will point out what I have left out, and they'll be absolutely right. I will have left out something important I'm sure. There are a few things that pop to my mind. Passion is probably the first one. There's this unrelenting passion that translates into drive that I've seen in some of the best leaders. They are really unstoppable. Resilience is another word that I think is allied to that. They see obstacles as challenges to figure out a way to surmount, rather than something that stops them in their tracks. They have a great idea, although they're willing to discard it or discard parts of it, if it doesn't work out. They don't feel like they are entirely wedded into one idea, so they have a kind of flexibility or adaptability.

They're able to inspire with this idea. I love the word inspire, because it's an inherently emotional word. It's not just something that's rational. The greatest leaders are not just these rational automatons. They're highly emotional, very personal figures, but the other part that has to go with the inspire and the dreamer is being ridded in reality, and it's the combination of inspiring and giving hope on the one hand, but on the other hand being grounded in reality and being able to explain it and define it to the people that are following them. You can't have one without the other. If you're just focused on reality without being inspirational, then you're depressing and boring, and it's going to be hard to get people to follow you. On the other hand, if you're only charismatic and inspiring without being ridded in reality, then you're in Lala Land, so it's the two that come together.

Charles Day:                         The notion of having passion, as you said, obviously critically important. Applying it towards a vision that actually is meaningful is essential actually. Right?

Kerry Sulkowicz:                 Yes.

Charles Day:                         The notion of here's the change that we're trying to make. Here's the difference that we want to occupy. I think there are not enough companies, not enough leaders that I come across who has really taking the time to ... It's in their head, or they think they've said it, but it very rarely comes out ina really kind of explicit and clear way that is actionable for companies. Do you see that as well?

Kerry Sulkowicz:                 Yes. I do. I think you said it well. I think that has to exist. You know, if you take one of my favorite little definitions of leadership, that at first blush sounds circular or tautological, is that the goal of leadership is to inspire followership, when I first thought of it in those terms I thought, "Well, that's not particularly helpful. It's going around in circles," but it actually isn't, because to be able to do what you just described, which is to define clearly where are we going, and why, and how, that's the way to get people to follow you.

Charles Day:                         Through a modern leadership lens that's become more important than ever, as you get millennials and Gen Y and Gen X entering the workforce. I think millennials are going to be the dominant part of the workforce in the next year or two, if they're not already. They have a different set of values, don't they? So, modern leadership has to evolve, it has had to evolve, perhaps not evolving fast enough to reflect how the workforce is changing.

Kerry Sulkowicz:                 I think that's true. I think some of the fundamentals of leadership probably haven't changed since the dawn of time. We've had leaders since the dawn of time, but yes. Our times are changing and values are much more upfront now. You know, I think about my kids, who are in their 20's, and I've learned so much from them. One of those things is that young people want to hear about values first, and if the values aren't there, the rest of it doesn't really matter.

Charles Day:                         You were saying earlier that leaders often try very hard to put aside their valued work and do it later, but as you've said, I see this as well, that there's nothing more important. As you start to work with a leader on defining that, I'm really curious to know how you go about that. I hear leaders say ... I mean, we start to do the work, and most students will sit up there, and somewhere in the first three values they say honesty. You say, "Really?", and they look at you incredulously, "Of course. Why would I not want to be honest?" Then you pose to them a scenario in which they're having a meeting with somebody that they know is being fired on Thursday, but they can't fire them today, because the general counsel's out until Thursday, and so they're asking about their future. Are you really going to be honest with that person in that moment? How do you sift through the theory of values, the esoteric, wonderfulness of some values versus the practical implications that a value needs to be important all the time, not just when it's convenient to you?

Kerry Sulkowicz:                 I think the micro-example that you just alluded to takes us beyond the idea of trying to define values in the form of whether that's a values statement of something that the leader needs to repeat all the time. It gets right into the work that we, as advisors, do, which is that's the kind of conversation I want to have with a CEO. I don't know the answer to that exactly, but those are the tough kinds of situations, and there are an infinite number of them that are equally complicated. That's where it is. We want to have those kinds of conversations and to help leaders struggle with them in a productive way.

Charles Day:                         Given that you can't generalize these things, what have you seen consistently to be true about when a leader sits down to define their values? What are the things that actually stick and last? What are the characteristics that you look for in helping them make sure are these real, are these valid?

Kerry Sulkowicz:                 Sometimes I've spoken to some CEOs who when trying to do this, try to come up with values in an abstract sense about the values of the company in way that is sort of disembodied or disconnected from their own personal values. That doesn't work very well, because they don't really have that much meaning. They're abstract and a little bit of kind of a motherhood and apple pie set of values, not that there's anything wrong with either of those things, but they have to come from the inside of the leader. You know, if one leader has a particular passion about the environment and climate change, for instance, if that's their personal passion and it happens to dovetail with the work of the organization in some ways, then that's really going to resonate. There are many examples like that, that there's got to be a connection between the individual leader, who's going to be the standard bearer for these values, and the values of the organization.

Charles Day:                         I know you do a lot of work around CEO transition. You work with boards a lot. When you're looking for the successor, this notion of the organization's values and the individual values, they have to be in sync. Right?

Kerry Sulkowicz:                 They do, although in a CEO succession situation you also need to be prepared for the values somewhat changing from the outgoing CEO to the incoming one, whether the incoming one is coming from within of from the outside.

Charles Day:                         You mean the organization's values?

Kerry Sulkowicz:                 The organization's value is changing somewhat, consistent with what I was saying a little earlier in this conversation about the way the culture changes when a leader changes. Values are very much part of culture I think.

Charles Day:                         That's a fascinating idea, because I think a lot of organizations, when they're making changes at the top, look for somebody who fits exactly with who they are today, what the organization is today, but your point is there has to be some give and take on both sides, that part of bringing a new leader is to allow the organization to evolve as well.

Kerry Sulkowicz:                 It's going to evolve, whether they like it or not, so they might as well be open to it and embrace the idea of it changing. Again, I keep coming back to this, even being deliberate about it. The outgoing CEO may have been successful for a long time, so it's not knocking him or her, and the way they did things, and their values, but to try to find a clone inevitably leads to failure, because of course that doesn't exist, and so it's a time to engage the board in thinking, "Well, all right. It's a loss for us, sure. This person's retiring after a successful tenure, but how do we think about where the company needs to go in the future? How might the culture and values evolve to keep pace with the changing external realities? What kind of leader do we want to see going forward?" It's not going to be the same as the old one, and that's okay.

Charles Day:                         One of the places that I see as being most challenging, in terms of leadership transition, is when somebody is taking over for the founder in a closely held organization that has really been built around a cult of personality kind of dynamic. Inevitably, in those situations the founder has some sort of mystical, legendary status. They have been turned into sort of an [etherean 00:36:28] figure. These new leaders come in, and my first reaction is sympathy, because I think, "You can't possibly live up to that yet. You haven't done it for as long. Everything that the organization is describing is framed through this legendary figure." When you encounter situations like that, as I'm sure you have, how do you help the incoming leader rise to meet that [unmeetable 00:36:53] challenge initially?

Kerry Sulkowicz:                 Yeah. I've done a lot of work in transitions in founder led companies, and they're always fraught. That doesn't mean they can't work. In fact, often they work out quite well, but again, the one really key notion here is the idea that no one will replace the founder, at least not in the same way that the founder inhabited the role. Nobody can be another founder. There's only one, and so there's a process of mourning that has to go on, on the part of the board, the entire organization, to recognize that the new person, no matter what he or she is going to be, he is going to be different, really different. The founder, if the founder has died, that's one set of circumstances. If the founder is retiring or handing it off while still compos mentis to the next generation, it's very different, so each situation is really unique.

Charles Day:                         Yeah. I always found those dynamics to be absolutely extraordinary in so many ways. There's a couple of other things that I just want to get into a little bit. I have come across, and again, I'm certain that this is true for you, you see leaders acting against their own self-interest all the time. They can have a clear vision. They can have a very powerful effective leadership team around them. All the pieces can in a sense be in place, and yet you see leaders making decisions that act against their own self-interest. Why is that?

Kerry Sulkowicz:                 The not very helpful answer would be that they're human, though that is true. Last time I checked they're all human, and humans sometimes do things that aren't in our best interest, but I mean that seriously, that leaders are subject to the same conscious, and more importantly, unconscious forces that the rest of us are. They sometimes feel anxious and do things out of anxiety without thinking about them enough or without trying to think through the unintended consequences that wind up backfiring. Leaders sometimes feel guilty about their power and their success and do things to detract from it and even undermine in. Leaders are subject to the same unconscious drives and conflicts that the rest of us are.

Charles Day:                         When you see that happening, how do you go about helping them to recognize the inconsistency of their stated goals and their actual behavior?

Kerry Sulkowicz:                 Well, we try to step out of the fray, out of the intensity of the moment and reflect on what they've done or what they're considering doing, which is even better, before they've done it. One of the things that I tell leaders, and they're probably sick of me sounding like this, but I tell them that sometimes when they're confronted with a really difficult problem, which if they're really honest, is probably every other day, that sometimes the best thing to do is nothing. Of course, they look at me like I'm nuts, but I don't really mean nothing nothing. I don't mean that they shouldn't take action, but maybe they shouldn't take action right away. Maybe the best thing to do is to step back, what seems like an emergency maybe can wait a day or two or a week, and to reflect. That's the space that we try to create, so we can actually talk about it. Sometimes better ideas, better information percolates to the surface, and they're able to take actions that are less counterproductive.

Charles Day:                         Is that a hard message to get across. Do you find that most leaders who've reached that sort of prominence are there because they feel like they need to be action oriented or they have been action oriented in the past?

Kerry Sulkowicz:                 Yes. They do. The more experienced CEOs kind of get used to thinking this way, and it becomes more natural and automatic for them over time. I see this particularly in new CEOs, people who are CEOs for the first time. I see this a lot in the leaders of start ups, the entrepreneurs who I work with. They somehow have this caricature embedded in their minds about that as a CEO they have to be doing something all the time, and that's actually not true. They should be thinking all the time, and talking to people, and gathering information, but they don't have to be doing something all the time. They don't have to be in action mode. If they create a little time, I'm not talking about a week, even just a few minutes sometimes to reflect, they make better decisions.

Charles Day:                         When you see CEOs, leaders of any description, taking on new positions, what's the biggest failure do you think in the first 100 days? What's most likely to trip them up in the first 100 days? It'll be of their own making.

Kerry Sulkowicz:                 Well, I could come up with a long list. There are a few things that I would say. I'm sometimes asked what's the most common mistake that leaders make, and this is particularly true in the early days, is that they don't act quickly enough on people problems.

Charles Day:                         So true. It's amazing how often that happens. Isn't it?

Kerry Sulkowicz:                 Yeah.

Charles Day:                         Staggering.

Kerry Sulkowicz:                 I mean, sometimes they indulge in all sorts of wishful thinking, that because of whether through the force of their wonderful personalities, that the problem person is going to see the light and get whipped into shape. That rarely happens. Or they see some kind of destructive dynamic on a team, and they try to fix it, which is a noble thing to try to do, but often these deep rooted problems can't be fixed, and people need to be changed out I think.

So, leaders need to have a team that they not just have confidence in, in terms of their various competencies that are represented, but in terms of their relationships. They have to like coming to work every day with this group of people, and if they don't, then there's something wrong with it. I encourage leaders not to act rashly on it. They may not be able to figure this out on day one. In fact, I would urge them not to, but you talk about the first 100 days. By then you kind of know what you've got and need to make some changes, and it's rare that somebody inherits a team that is just perfect for them as a leader. It may have been just great for the last guy. That's one.

I think the other thing that leaders do early on that's a mistake is they feel they have to prove themselves too early, and they don't do enough listening and learning in the early days. Again, that's not indefinite. At some point they actually have to do something and show some results. They have to be productive, but building the relationships, listening, learning in the early days is the most important thing to do.

Charles Day:                         Yeah. I see that myself. I like to talk about leaders walking into situations in which they have access now, for the first time, to the levers of power, and knowing when to actually use them and activate them is very, very important. I think, to your point, the situation that I see over and over again is this resistance to making obvious personnel changes quickly, and it bogs the organization down for months, if not years, in many cases.

Kerry Sulkowicz:                 Yeah. It really does. The other things that it does, if they don't act in some due course on these kinds of people problems, it starts to undermine their own credibility as leaders, because the organization is looking at the situation thinking, "Well, what's wrong with this CEO? Doesn't he see the problem?" Or maybe the person has a values problem. If the CEO doesn't act on it, what does that say about the CEO's values?

Charles Day:                         I'm curious to get your thoughts on this. I don't know that you and I have ever spoken about this, but I have come to believe increasingly that as human beings ... This is not new thinking, but as human beings, we tend not to see our own strengths. We tend to worry about our own weaknesses, for some of the reasons we've talked about in the last few minutes, and therefore the things that we are naturally gifted at, brilliant at in some cases, we tend to underestimate, because they're so easy we assume everybody can do those, and we focus instead on the things that we're not very good at. The evolution of that thought to me has become the notion that there is essentially somewhere inside everybody a truth about who we want to be, the difference that we aspire to make, and most of us grapple with that question in some fashion or another. Do you see any evidence of that kind of reality, that kind of perception, in terms of the people that you encounter?

Kerry Sulkowicz:                 I might put it in somewhat different terms, but I think I know what you're talking about. What your question, Charles, makes me think of is an artifact of the coaching culture these days, which has changed the business world so dramatically in the last roughly couple of decades, in which it's become so commonplace, going from something that was shameful to something that's a badge of honor. My coaching culture, I'm really using that very loosely to define a culture not only of organizations sort of teaming with all sorts of coaches and training, but also with the prevalence of feedback, 360 degree reviews and various instruments to gather feedbacks. In some ways that's healthy.

I think people should be open to getting feedback. But I think the focus tend to be on what's wrong, and we can always find something, because none of us are perfect, but it's fairly well known that when people are delivering feedback, the recipient skims over the good stuff and goes right to the back page, so to speak, that has the negative feedback on it, an understandable human impulse to be sure, but not enough attention is paid to what is good and helping channel leader into doing more of what they're good at. I think that if we were, again, rooted in reality, we're much better off focusing on and enhancing those areas of strength, rather than trying to change the areas where we're weak, because human beings are so largely fixed by the time that we're adults, that it's less likely to be successful to try to fix the deficits than to enhance the strengths.

Charles Day:                         Yeah. That's really well put. Do you think that it requires different kinds of skills, from a leadership standpoint, to unlock creativity?

Kerry Sulkowicz:                 Yes. This is something that I would defer to your expertise on, but creativity I think exists in everyone to varying degrees. I don't know that creativity is learned. I think unlock is the right term. I think it's about removing the barriers to it. Some of those barriers are entirely unintentional, but powerful, and some of them are institutionally embedded. I think the most enlightened leaders have some sense of that. Sometimes the most creative people are also the most quirky and the most difficult to manage, and so organizations that try to clamp down on eccentricities or that have an intolerance for difference, are the organizations where creativity I think has the hardest time flourishing. I think the leaders who, on the other hand, have a high tolerance for quirkiness and difference are probably places where creativity flows more naturally.

Charles Day:                         I agree with all of that. I think that all of that resonates with me. The other questions that strikes me that I'd love to get your thought on, you've touched on this a little but, I think it was worth delving into for a little bit longer. The modern role of leadership advisory work, as you said, coaching, to use the phrase that neither one of us particularly like, used to be seen as a remedial tool, something you did to somebody who was struggling or failing. Today in many cases it's evolved, and it's seen more positively, but I still find that there are situations in which there is a sort of a set amount of time that's prescribed for a coach to work with a leader, and that when that calendar rolls over, all the alarm goes off that the work ends, because the time is up.

To my way of thinking, leadership these days has become so demanding and so challenging, and because the role of the leader is so valuable ... This sounds like an ad, and I didn't mean it to be, because there are clearly thousands and thousands of people who advise leaders in incredibly powerful ways. but the notion that leadership support should be an ongoing practice increasingly seems to me to be the right approach for companies to take, and embedding that into their operating process and even onto their P&L seems to me to be essential, that if I was looking to invest in a company, I'd want a company that was prepared to support its leadership team with that kind of consistency.

Kerry Sulkowicz:                 Well, you won't be surprised to hear me agree with you wholeheartedly on this, but I think that's the exception rather than the rule. Those are the more enlightened companies, in my experience. The time limited approach to coaching, I mean, I'm sympathetic to it in only one regard, in the sense that it's expensive. I can certainly understand why some companies give the ownership to that kind of experience to the HR department and put some strict limits on it, but I think it's unfortunate.

I think that there's a difference between coaching and advising leaders and coaching and advising managers. I think there are far more managers and should be far more managers deeper in organizations than leaders. The leaders tend to be at the top of the whole organization or top of parts of it. I think the leaders should have an ongoing advisory relationship with somebody. I deeply believe that. I think every CEO in the country should have an advisor for the duration of his or her tenure, period. I think with managers I think coaching is much more about training than it is about the ongoing advisory relationship with a leader.

By the way, I want to make it very clear that I'm not making any kind of value judgment about the difference between leaders and managers, but I do think that they're quite different, and we need both. We need many more great managers than we do great leaders, so I think organizations aren't necessarily as intellectually rigorous about it as they should be, about the difference between managers and leaders, and I think our culture has tended to valorize the term leaders and tends to therefore call everybody a leader when it's a misnomer for a lot of people.

Charles Day:                         The last thing I want to touch on is something that I don't know that you'll be thrilled to have this conversation, but I'm going to throw it at you anyway. You have built a remarkable group called the Boswell Group, and I say that it's remarkable, because you were kind enough to invite me in, and I've experienced it firsthand. It's a group of people who believe in psychodynamic advisory work for leaders, and many of the people are psychoanalysts and psychologists and a few of us are not. At my first session that I showed up at the phrase that came up three or four times in the first morning was murderous intent. I kept hearing this, and I was drawn to it, as you might imagine, and stopped and asked someone at the break, what did murderous intent mean? I told this story a number of times, but it will be a more relevant and valid explanation if it comes from you, the psychoanalyst and psychologist, than if it comes from me, the layperson.  What does murderous intent ...? What is the reference point for that?

Kerry Sulkowicz:                 First of all, thanks for the kind words about the Boswell Group. It's a terrific group, in part because of people like you. It's a diverse group of practitioners who I think share a number of values, speaking of values, in common. We're certainly not all coming from the same background. I do remember the surprise on your face when that subject and that phrase came up at your very first retreat with the Boswell Group. I think that's an example of the way psychoanalysts think it that we try to get down to the deeper human impulses that exist in all of us. The one that we happen to be talking about in the conversation that you're referring to was about the desire to do away with someone, to kill someone off.

Those impulses are ubiquitous. Those aren't just for people who are on death row for having committed a murder. We all do that in our hearts sometimes, but never act on it, but those impulses tend to come out in the form of competitiveness in the workplace, the desire to win, to get something, and thereby deprive somebody else of getting it. That's the nature of the human condition, that we have impulses, whether they're murderous, or sexual, or hungry, or whatever they might be, but there are these base human impulses that we all need to own in ourselves. Why shouldn't we see them in the workplace, albeit in very attenuated forms most of the time? Not always. Sometimes they come out quite directly. I think that's a difference between the psychoanalytic or psychodynamic, those terms or really synonymous, perspective and the more sort of positive psychology, happiness kind of perspectives that are prevalent in some other quarters, which I tend to think are superficial and don't really get at the deeper motives that drive human behavior.

Charles Day:                         Yeah. I'm often struck in my work when looking at a situation, how often you hear a leader trying to interpret through the lens of strategy, or sales, or business development, or some practical component, whereas the reality is that what they're actually struggling with, either with themselves or people around them, is some very, very basic human dynamic and human condition. Whether we see it through the lens of something like Maslow or something else, the fact is that those currents are very, very powerful and run deep within all of us. If you're not willing to address those and face those head on, get some help with those, they're going to get in the way. Kerry, I really want to thank for being here today, and this high school been a fascinating conversation, as always, and I look forward to seeing you at the next Boswell retreat, if not sooner.

Kerry Sulkowicz:                 Thanks, Charles. Always great to talk to you.

Charles Day:                         At the end of each episode, for those of you who listen regularly, I like to summarize what I've just heard over the last 40 to 50 minutes from each of my guests in a little section that I call the three themes. I didn't do that very well with Kerry, and so this is not done live, in all transparency, but having listened to the conversation we had, there are I think three very important themes that come up from talking to him that I think are foundations for great leaders. Kerry is not a leader of a business per se. He works for himself as a confidant and as an advisor. He has developed the Boswell Group, which has become very much a community, but I think that there are three themes that Kerry reflects in how he shows up that I really do think are the foundations of great leadership.

One is that Kerry has an enormous amount of empathy for the other person's point of view. He is willing to look at it from somebody else's perspective and to take time to reflect on that and to see what he can make of that. He doesn't disavow his own values and his own principles in any way when he does that, but he does stop and think about the other person's perspective before he makes a final judgment.

The second thing that he does extraordinarily well is he listens. Obviously as a psychoanalyst and psychiatrist, that's fundamental, and to some extent that is trained, and to some extent that is genetic. I've been conscious in my own development as an advisor, as somebody who is there to help people, that my listening skills have improved dramatically. Kris said to me a little while ago that she's not sure that three or four years ago I could have done this podcast, because perhaps I didn't listen as well as I might. I think there were certainly occasions where that is true. I think I've become a dramatically better listener, as my ability and desire to help people has become a more and more prominent part of my life, and I do think that listening is a learned skill, and it is a foundation of really great leadership.

Then I think the third trait that Kerry exhibits is that of generosity. Generosity is one of those traits that tends to be instinctive for some people and less so for others, but I thin the willingness to invest in other when you are the leader is foundational, and it can absolutely be the difference between somebody that works for you becoming successful and not making it. There is a fine line between generosity and indulgence, and I am always conscious of and sensitive to that when I am helping people who are leading businesses, because the other side of that coin is a willingness to continue top invest in people for whom this particular organization and this particular position is a bad fit, and that happens only at the expense of the organization and the other people around, who are doing actually great work and not requiring that kind of investment on a personal level. So, there is a fine line, but I do think that generosity is a very, very valuable and important trait in leaders.

That's my summary of this week for the three themes. I hope you've enjoyed this conversation with Kerry, and I look forward to seeing you next week on Fearless. You've been listening to Fearless, the art of creative leadership. If you like what you've heard, please rate us on iTunes. It helps a lot. If you want more information, the others, go to fearlesscreativeleadership.com, and thanks for listening.