The Bregman Leadership Podcast
Episode 116

Carter Cast

The Right (and Wrong) Stuff

Why do talented people face career derailment? If you know your faults, you can find the type of work environment right for you, says Carter Cast, author of The Right (and Wrong) Stuff. Discover the five derailment personality types in depth, how we get “stuck” – and what we can do propel ourselves forward.


Do you have a problem with ego management? You might be Captain Fantastic, according to @CarterACast Listen now: #podcast #TheRightandWrongStuff #amreading  What kind of person requires a “strong cup of coffee”? @CarterACast and I discuss personality and behavior types on the #podcast




This transcript has not been edited.

Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host, and CEO of Bregman Partners. This podcast is part of my mission to help you get massive traction on the things that matter most.

We are fortunate enough today to have with us Carter Cast. Carter wrote most recently the book “The Right and Wrong Stuff: How Brilliant Careers are Made and Unmade.” Carter is friends of [inaudible 00:00:38] of mine, and they all spoke super highly of him, so I’m very excited, Carter, to have you on the Bregman Leadership Podcast. He is the clinical professor at Northwestern’s Kellogg School of Management, and he’s a venture partner at Pritzker Group Venture Capital. So, he is both a professor of entrepreneurship and an academic, and also a practitioner and investor. And that is a great combination, ’cause we’ll be talking with Carter both about the theoretical and the ideas, and how he’s formed them, but also how you implement them and how they really play out in real life, which is, as you all know, something I care deeply about. Carter, welcome to the Bregman Leadership Podcast.

Carter: Thank you, it’s good to be here. Thank you very much.

Peter: So, Carter, anytime any of us writes a book, we’re dropping years of care and focus into the topic. And it’s an interesting topic for you to have chosen. You approach business both from the human side, and also you’re at all levels. You’ve been a general manager. We’ve talked about, you work in venture capital to helping them to scope out deals and support deals. Why this? Why focus on the right and wrong stuff related to careers? What motivated you to write this book and drew you to it?

Carter: Well, you know how they say, “Write what you know?” I had a nice flirtation with career derailment in my 30s that kind of flat-lined my career for several years. The experience stayed with me, and I realized that, even if you built a set of skills and you’re motivated, that a blind spot or a area of vulnerability that you don’t have a good handle on can sort of sweep you at the knees. So, I think the experience just was embarrassing and stayed with me. And now, I’m a teacher and I work with entrepreneurs, but I also teach at Northwestern at Kellogg. I probably talk to 15 or 20 millennials a week, and I’ve done it for seven years. And, they’ll come to me asking about, what should I do with my career? Should I go to McKinsey or should I go to the Series A startup? And you’re trying to unpack the question, and so you say, “What are you good at? What do you love doing? When do you raise your hand? Where do you see yourself in five years?”

And then, I’ll ask this question, every time. Invariably, it gets them stumped. I’ll say, “What about you could hurt you?” And, I have gotten so rarely a good answer, that I became convinced that the strengths movement was so stressed that people weren’t looking at the flip side, which is, a lot of times, a strength has a … an overdeveloped strength has a weakness, the flip side of a coin.

Peter: Always.

Carter: And I felt like the topic, I hadn’t read a lot about it. And so, I did research, and I realized that there’s a tremendous amount of derailment literature from CCL, and from Hogan, and from [Cornfarian 00:03:49], and there’s just so many sources and a lot of academic research studies. And then, on top of that, I interviewed people who had gotten fired or demoted myself, and talked to executive coaches, and then realized there’s a lot about this topic that hasn’t been brought up to the layman. And so, I wanted to write about a sensitive topic.

Peter: It’s interesting. And is that question that you ask, what might derail you, in a sense, different than the question that you often hear in interviews, which is tell me your greatest weakness kind of thing. Is there something slightly different about the way you’re asking the question?

Carter: Oh, I think so, because I can tell you a weakness that I understand and I’ve created some compensatory strategies for. I can tell you about areas of vulnerability that I have under control now that I’m older and have gotten punched in the face a few times. But, this topic of what you don’t know can hurt you so much, and I experienced it first-hand with sort of an oppositional defiance disorder with authority figures that I did not have under control, and it hurt my career.

Peter: So, I love what you’re saying about this, and it brings me down to a critical question I had as I was reading this, and I want to go through … You list in the book very beautifully five core derailers. Five typical derailers. But, you just mentioned this issue of blind spot. As a coach myself, I find myself struggling with this often, which is, blind spots run deep, and they exist to protect fragile egos. And people … there’s a tremendous amount of armor and defense against seeing your own derailer. There’s a lot of people who are very successful but have ultimately fatal derailers, which at some point will get them. And, they could be … Let’s put aside the Harvey Weinsteins of the world, where … But, that’s also very well maybe manipulative, maybe a blind spot, I don’t know. I don’t know that it’s useful to talk about that.

Carter: Or the president.

Peter: Or the president. But, there are so many people who are relatively functional but create incredible toxicity in organizations, leaders, and who don’t see it. And when told about it, will assign blame everywhere but themselves. And maybe they’ll take some of it, but they’ll put so much on other people that it protects them. And my question to you is, how do you, in all of your experience, what have you seen helps to pierce the armor of the blind spot that allows someone safely enough to be able to look and own their own counterproductive behavior?

Carter: That’s a really tough question. Mike Tyson, the great Mike Tyson, the philosopher Mike Tyson. Tyson said, “It’s good to have a strategy until you get punched in the face.” And then all of a-

Peter: And he had his own, pretty obviously self-destructive tendencies that have left him, as far as I know, kind of broken and done. But yeah, there’s strategies, great strategies until you get punched in the face.

Carter: And I think, when you get punched in the face, often, you recognize that something that you weren’t aware of or that you were aware of in a minor way could be a lot more damaging to you than you thought. So, sometimes, it takes a two-by-four to the side of the head, or 360 feedback from plenty of peers, your subordinates, and your superior, that is so consistently bad or tough around the area of vulnerability that you finally have to wrestle with one of your demons or one of your areas of vulnerability.

Peter: So, let me just go into that a little deeper, ’cause I think it’s really interesting. So, in a sense, if someone fails, but not enough to totally knock them off their feet, then they can continue in the blind spot delusion. But, it requires a really aggressive hit. Meaning, it requires the confrontation of true failure for them to be able to look … they have to hit whatever rock bottom is to them for them to say, “I’ve got to change something.” If their ego is fragile enough that the armor is strong.

Carter: Well, let’s categories these derailment propensities. One, some are scale gaps. Which you can fix if you’re committed. Some are, you’re in the wrong context. Your motive structure doesn’t fit your jobs. You’re in a early-stage company, but you require structure. You desire structure and you should be in a later-stage company. You’re in a matrixed organization and you desire autonomy. Sometimes, you’re in the wrong context. You can fix that if you work on becoming more self-aware and understanding your motives. If you have a-

Peter: I’m realizing you’re going into them, so let’s do that. I think that’s a great thing. Let’s go through each of your five. Let’s start with Captain Fantastic.

Carter: That’s a tough one, because what you’re getting at is, interpersonal issues that are often deep around personality components that we’ve gotten grooved over the years. And, my dad had a oppositional defiance disorder to authority. My grandfather did. My sister does. And so, for me to work on this, this is genetic.

Peter: And how would you describe it? The Captain … Describe it in a sentence so that listeners …

Carter: Captain Fantastic has a problem with ego management. He doesn’t listen. Doesn’t enlist other people. And, is often self-serving, I me mine, and bruises people on his quest for the holy grail of the corner office. And he does fine, ’cause he’s self-promoting, until he misses a quarter, he misses a year in the business plan, and nobody’s there that wants to support him.

Peter: And this person will tend to look at failures and assign them to the people around him, versus take responsibility and say, “I did something that caused this.”

Carter: That’s right. And what’s funny is, Captain Fantastic happens … In my research, I saw it much more in … later in the career. You get a certain amount of success, and you start thinking you have the answers, and you stop listening. And you get too far removed from the front-line workers to … They have the answers ’cause they’re closest to the customers.

Peter: Right. It’s kind of interesting, because you can look at it one side and you go, success confirms their self-perception. And, on the other hand, you can look at it and say, “Maybe they are smarter.” You know, if they’ve been successful time and time again … I’m curious about the point at which they might be right. Or, they might just be an ego. Can you talk to that a little bit?

Carter: Well, I have been in … I worked for PepsiCo 11 years. I worked for Walmart seven years. I’ve been in these big companies, and PepsiCo was a culture that almost embraced these Captain Fantastic characteristics. It was sort of … They said “Pepsi pretty” and “big blue,” and we dressed in suits and ties and starch shirts. They loved to see these young Turks go flying up the organization that were aggressive and had sharp elbows. They did very well, until they got into tremendously complex jobs which required cross-functional savvy, great teamwork, and shutting up and listening to people who understood more about engineering, or sourcing, or a big data set.

Peter: So, they really succeeded in the context of being an individual contributor within a silo. But once they rose high enough that it required managing a matrix or within the network, or cross-silo, they fell down.

Carter: That’s right. When it’s cross-silo, and there’s shared accountability, and you don’t have all the resources sitting under you that you can demand attention to, that’s when they run into trouble.

Peter: Got it. How do we help these Captain Fantastics?

Carter: Well, this is the one that I think is the toughest, because some of the other ones I can go into, they’re more about skill gaps or lack of access. But, Captain Fantastic is about you and the way you see the world, and personality characteristics. And you know Robert Hogan. The Hogan looks at 11 dysfunctional … Kind of Jungian, dark-side tendencies. And Captain Fantastic, I just took the biggest one, which is someone that is excitable, and bombastic, and volatile, but there’s other pieces of the Captain Fantastic characteristic. You could be aloof, reserved, highly skeptical. Either way, you’re moving yourself away from other people, not towards other people.

Peter: And is the only solution to that one, then, epic failure?
Carter: In my experience, and in reading what I read … Sydney Finkelstein has some great stuff. There’s so many … Robert Caro, Dave Dotlich. There is … A strong cup of coffee is often required.

Peter: Right. Got it.

Carter: In some form.

Peter: Okay, the Solo Flyer. That’s the second derailment.

Carter: That happens early in the career. That’s your strong individual contributor that gets promoted because they kick ass and take names. They’re great at doing, at executing. But, they get promoted into their first managerial job and they keep trying to do it themselves. They don’t go from me to we. Linda Hill of Harvard said that, “Becoming a manager is literally a transformation of identity.” I love that phrase she uses. And they don’t realize that their satisfaction has to come from enabling instead of doing. And, this is something very fixable. You just have to learn that there’s a mindset shift, and you have to coach and enable, and not do. And that’s tough for people that are really good at doing.

Peter: It sounds like some of the source code for the Solo Flyer might be found in Captain Fantastic.

Carter: That’s interesting. That’s a good correlation I should look into. That could very well be the case. I think a lot of times, it’s just a matter of learning to trust, and learning … so trust, but verify, as Reagan said. But, this is a fixable one, and I saw this a lot early career. But, you can work with people.

Peter: The best way to help someone fix it?

Carter: The best way to help someone fix this is to get them to learn to trust their teams. The more you get to more people, generally, the more we trust each other as humans. So, by spending more time with her team and asking, “What are your goals? What are you trying to accomplish? How can I help you reach them?” That you’ll start having this reciprocity between the subordinate and the superior that will lead to trust and the superior, the coach, will start letting go and letting the person run more. So, I think it’s about getting to know your team better and more deeply so you begin to trust them.

Peter: So, here’s a possible way to diagnose yourself as to whether you’re more Captain Fantastic or Solo Flyer. Which is, if you find yourself resistant to doing what you just said, which is asking and listening and caring what the people around you say, then probably, you’re more Captain Fantastic. And if you look at that solution and go, “Oh, that would be very useful to listen, and to ask questions, and to understand their perspective, and to possibly mediate what I’m doing with the knowledge that I’ve gained from their insights,” that might make you a little bit more of a repairable Solo Flyer. Am I thinking about this correctly?

Carter: Yeah. I think that’s brilliant. I love that.

Peter: Awesome. Version 1.0. That’s a third derailer.

Carter: Often happens mid-career. You get in a groove, and the groove turns into a rut. You get complacent, and you stop having that learner’s mindset. The discovery skills, experimenting, observing, questioning, networking, you stop doing those things that sharpen your saw and, if I asked you about artificial intelligence as it relates to voice recognition, you wouldn’t know what I’m talking about. Or, if I asked you about big data sets in IoT machine learning, you’d say, “I don’t understand that.” In this day and age, we have to stay hungry for knowledge and information.

Peter: Got it. And, are those people usually self-aware, or they don’t realize they’ve been stuck in a rut? And so, the remediation here really lends itself to increasing awareness that there’s a whole bunch of stuff you don’t know that you might need to.

Carter: That’s absolutely right. I think this is increasing awareness, because they’ve gotten in sort of a groove, or in a silo, and they need to be broadened. Then they’ll realize, boy, I got to get out there. I got to tour with the sales folks. I got to talk to suppliers. I need to do a competitive audit. I need to go out and do some primary research on our customers. They have to get out of their office and into the market more.

There’s a second side of this Version 1.0, which is, people that are basically recalcitrant and inflexible by nature, that aren’t adaptable to changing circumstances, getting a new boss, a new technology is used in your company, you go from a functional organization to a matrix structure and they fight it. So, there are some personality characteristics that can hurt people just around not being flexible and open-minded here on this.

Peter: How do you imbue the inflexible with some flexibility?

Carter: One of the things you can do is, I ask people, before you speak, just ask a lot of questions. Go into meetings, and try to reserve judgment, and spend … There’s this great stat by Clayton Christensen. He said that, in his research, “Innovators have a ratio of six to one on questions asked to statements made.”

Peter: So, possibly the most important skill that we can teach the Version 1.0 is … and actually, it sounds like also the Solo Flyer. Maybe all of these. Is, curiosity. Right? [inaudible 00:19:22] help people to be naturally more curious, they’re gonna maybe get out of their ways a little more.

Carter: Which is why I’ve taken Carol Dweck to dinner three different occasions.

Peter: She’s a lovely, lovely person, isn’t she?

Carter: Lovely person, and the growth mindset is what we’re talking about here, right? We’re talking about not having a fixed mindset where there’s a zero-sum situation. If you fail, you don’t see it as a failure. You see it as an experiment that you learned from.

Peter: Right. Right. Now, distinguish for us Version 1.0 from your next derailer, the fourth one, the One-Trick Pony, because it seems like there’s a relationship between those two.

Carter: The One-Trick Pony has gone up the ladder in a vertical way, and they haven’t broadened their skill set, so they hit a ceiling in terms of their promotability. So, they’re too narrow and they’re viewed as non-strategic. This was the number one derailer of women. Number one derailer.

Peter: That’s interesting.

Carter: Yeah. And I think … When I give a presentation, I’ll say … to the audience, “Well, do you just think women are less strategic than men from a genetic standpoint?” And people will grimace at me, and I’ll say, “Well, of course not. This is a problem of access. Having access to different jobs, to different mentors, to different counselors. Broadening your perspective by being rotated into different assignments.”

So, the problem here is, like you might have a controller that wants to become a CFO, but the controller has never had any visibility into capital asset management, or forecasting tools, or whatever. I would say five to eight years into your career, you might be a functional expert at that point. You know, the old 10,000 hours at five to eight years, and it’s time to start looking for step-out opportunities.

Peter: This also brings me to the importance of leadership around people’s careers, and the role of the organization, and I can see where the role of the organization for Captain Fantastic might be to ensure for his own good a degree of failure. Meaning, to create the boundaries that don’t allow this person to be so successful with that behavior, so that the natural consequence isn’t so catastrophic for the organization, but taught early on. And it seems like for-

Carter: Yeah, I think that’s a great point. And I think that would be … Little tests like that that challenge Captain Fantastic’s self-conception, and offer him learning experiences.

Peter: Right.

Carter: Through failures. Through little failures.

Peter: And it seems like the opposite approach would be useful for the One-Trick Pony, to basically create support mechanisms, and mentorship, and opportunities to broaden their scope and awareness so that they can become more strategic. And maybe that’s true for Version 1.0 as well.

Carter: Yeah, I think that’s absolutely true with the One-Trick Pony. You always get asked as a follow on question to this one is, “Well, how do I get mentors?” And I’ll say, “You don’t just want one mentor. You want a bunch of counselors. You want a mosaic of mentors. You want, maybe Carter for demand generation in a digital world, and you want Peter for leadership, and you want somebody else for supply chain. But, pick these pieces of people where they have areas of expertise and leverage them instead of kind of hanging it all on one mentor to …

Peter: That’s a great, great point. And certainly don’t go to me for supply chain management. So, let’s do this last one, the Whirling Dervish.

Carter: Yeah, this is an easy one, and actually, in the assessment tool I created where you can … I developed it with the CCL. You can take this test and see which of these five propensities you might have. This was the most, highest self-reported one. I have thousands of surveys on my website.

Peter: Right.

Carter: This one, this is number one. And this is the Whirling Dervish, which is, doesn’t deliver on promises because they’re over-extended, can’t say no, poorly organized, don’t prioritize, and as a result, balls drop and people start distancing themselves from this person because their word isn’t their bond.

Peter: And what you’re saying is that, most people are self-aware of that derailer versus the ones who fall into the categories of the other derailers.

Carter: Yes, or some of them, they just don’t want to painfully look at. It’s easy to say, “Oh, I’m so busy, I’m so wanted that I have a little bit of the Whirling Dervish in me ’cause so many people desire my time.”

Peter: Interesting.

Carter: Versus, “I’m non-strategic.”

Peter: Right. So, I feel good, if I’m a Whirling Dervish, it means I’m that important, and that … In fact, I can imagine a Captain Fantastic might be correlated with a Whirling Dervish too, to just say, “Ahh, I’m so in demand because I’m so great that I really have to get my … I need time management.”

Carter: Yeah. No one says they’re non-strategic. I do a workshop on this at Kellogg. And I have students sit at tables after they take the assessment. And the table is what their archetype is. And the table, I’ll have three tables of Whirling Dervishes. And I’ll have two people that are self-reported One-Trick Ponies. No one likes to say it.

Peter: And I guess my question is, if you look at the … Assuming people read the book, which I think you should, it’s a great book, and you self-identify as a Whirling Dervish, would you recommend that, if that’s your instinct, that you look a little deeper because there’s a potential that you might be missing one of the other four derailers and cloaking that derailment factor in Whirling Dervish overwhelm?

Carter: Yes. And I would go so far as to boldly say that every single one of us has interpersonal issues that are driven by some of our natural insecurities. And Robert Hogan, if you take the Hogan, he has 11 of these attributes in his Hogan psychology … development survey. And, everyone has at least one of these areas that flares. I had two. And so, I would argue, no matter who you are, you’re gonna have some dark-side tendencies that hurt you interpersonally if you aren’t aware of them and you don’t self-monitor them.

Peter: That’s interesting. And, that might also be a way of helping the Captain Fantastic become more self-aware. Which is, they might have a likelihood of not admitting to any real gap or derailment factor.

Carter: That would be interesting, ’cause-

Peter: And that would be interesting to say, “Well, okay, so everybody has them.”
Carter: Except you.

Peter: “And if you don’t know what yours are, chances are you’re this one.” That could be kind of interesting, too.

Carter, thank you so much. This has been a really fun conversation, really really interesting. I think I have the elements of all five of these, as do probably a lot of people. And I can see where, just seeing, without even labeling myself, just seeing the opportunities for growth in each of them is a very useful way to look at this too, which is to say, can I get better at being less Captain Fantastic, or less Version 1.0, or less of a Solo Flyer. And I think, for most of us, the answer would be yes to all of these things.

Carter: I’m so glad you said that, because this is not an indictment. We’re all human, we’ve all got these bumpy, jagged little areas that actually make us interesting. So, I love what you said. See these as ways to get even better, versus, these aren’t indictments on your personality, or … It’s just, I like the way you said that, because that’s what I believe.

Peter: I believe that too. Carter, thank you so much for being on the Bregman Leadership Podcast.

Carter: Thank you, Peter. Great questions, I really enjoyed myself.

Peter: If you enjoyed this episode of the Bregman Leadership Podcast, please subscribe and leave a review on iTunes. For more information about the Bregman Leadership Intensive, as well as access to my articles, videos, and podcasts, visit Thank you to Claire Marshall for producing this episode, and to Brian Wood who created our music. Thanks for listening, and stay tuned for the next great conversation.


  1. Pamela Moore says:

    Not up to the usual standard. This is too simplistic. I’m quite surprised because my understanding is that your business doesn’t endorse labeling and categorizing people into boxes. You normally recognize the complexity of leadership and this is far from that.

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