When it Comes To Work, Are You A Whirling Dervish?

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Pritzker Group Venture Capital: Carter Cast photographed at The Chicago Athletic Club, Chicago, IL. October 13, 2016. Photo by Andrew Collings.

[The following is the full raw transcript for a LEADx Podcast interview, which has been lightly edited for clarity.]

Kevin Kruse: Hello everyone, Kruse here. Welcome to The LEADx Leadership Show, where we help you to stand out and to get ahead. We help you to become the boss everyone wants to work for. Wow, today's guest is loaded with charisma, super successful guy, and super vulnerable, talking all about his failures instead of his many successes. We hit it off in the pre-show chat talking about our young kids and balancing all of that with being writers and entrepreneurs and everything else. We talk about five common ways people sabotage their career. He's got cool archetypes, like one he calls The Whirling Dervish. Another's Captain Fantastic. We talk about culture fit and a whole lot more.

First though, if you're the kind of person who likes to say thank you, I hope you'll thank the LEADx team by taking one minute to leave a rating on iTunes or wherever you listen to this podcast, and make sure to visit leadx.org for the free training course of the day. Doesn't even require an email. You just show up and watch and learn, and while you're there, check out the LEADx Academy, over 50 courses that will help you to stand out and to get ahead.

Our quote of the day: Turns out, the end of the last song The Beatles ever recorded together, it goes like this: “The love you take is equal to the love you make.” And this became a theme in so many of my guest interviews throughout the day.

Our guest for today's show was the VP of Marketing at Electronic Arts, where he launched The Sims. He then became the chief marketing officer of Blue Nile, which is the largest online seller of diamonds in the world. I actually think they might just be the largest seller of diamonds in the world at this point. He then moved on to become the CEO of walmart.com, third biggest online retailer behind Amazon and eBay. Today, though, he teaches entrepreneurs as a professor at the Kellogg School of Management, and he's also a venture capital partner at the Pritzker Group. His new book is The Right and Wrong Stuff: How Brilliant Careers Are Made And Unmade. Our guest is Carter Cast. Carter, welcome to the show.

Carter Cast: Thank you, I'm glad to be here, Kevin. Thank you.

Kruse: Now, I've got a tradition, Carter, where it doesn't matter who the guest is, they get the same first question, because I believe failures are stepping stones. There's no win or lose, only win or learn. And I've learned a lot over my decades. But I'm hoping you will tell us a story, like what's been one of your best failures in life? Because I'm selfish, I want to learn from your failures, not just my own.

Cast: Oh, I have so many to choose from. I'll pick one that's sort of relevant to our topic. I was brought into my boss's office 20 years ago when I was in my mid-30's and I was a senior marketing manager, so I was kind of mid-level management at Frito-Lay, and it was my performance review, and I was told I was unpromotable and I was told I was insubordinate and recalcitrant. I had to look up recalcitrant to look at what the hell that meant. And the guy kicked me off his team because he said I didn't follow his agenda. And I actually flatlined a couple years, I was sort of seen as toxic in the organization because I wasn't easy to manage.

And I had a blind spot, Kevin, I didn't understand, and I think in my case it's this almost an oppositional, it's an authority issue, oppositional defiance, but I didn't know it was hurting me so much, and so when this guy gave me this strong cup of coffee, kicked me off his team, my career flatlined a few years. I had to get my arms wrapped around a personality characteristic that wasn't so good. And it ended up being probably the best performance review I've ever had because it made me come and wrestle down this issue I have.

Kruse: Well, thank you for sharing that, and this is going to be a great lead-in in a moment to your book, of course, and I just want to share for our listeners that when I read this story in your book, that you just shared, I mean a couple things came to mind. First, it is an interesting example of how someone who can really be earmarked as a high performer or high-po, can suddenly derail. And I remember, I was 30 years old the first time an executive coach used this term derailer, “Oh, that's a derailer,” I didn't even know what that word meant. I found out quickly what it meant, but you used that phrase blind spot, and again, for our listeners, it's different than a weakness. A weakness is something you know it's there. A blind spot by definition, you don't know what you don't know, and we're going to dive into that in just a minute.

But I also have to say that when I read that story, what went through my mind is your boss wasn't a very effective leader because if you were shocked by that feedback in your annual review, he or she was not giving you effective feedback the previous 12 months, and I felt for you as a young man at that point that you weren't working in a situation where he didn't just grab you earlier to have that talk with you.

Cast: Well, you've hit on a really big theme of the research I just did behind the book, which is there is an enormous amount of organizational complicity in this topic of derailment. I think it's part of being in the gig economy. You know, we're in the years of the 1099 worker, and there's not this reciprocity, this sort of mutuality of, “I develop you and you give me years of service.” So I went to PepsiCo, they spent a year training me before I started my first assignment.

Kruse: Wow.

Cast: Just like P&G takes you out in the field and gives you sales training if you're a brand marketer. I spent 11 years there, and that's sort of the social contract. It doesn't exist anymore, and I think one of the outputs of that issue is organizations are not giving people feedback about their performance. They aren't being proactive in developing development plans that are based partly on skill gaps, partly on interpersonal vulnerabilities, and partly on strengths that they want to amplify. So this just isn't happening as much, and I've got a lot of data behind these comments. And as a result of it, you are responsible for determining your own blind spots, weaknesses, skill gaps, because nobody else is going to help you. Maybe you get an enlightened boss here and there, and if you do, you're lucky.

Kruse: I was going to say, I think you're lucky and you can't count on the luck. On The LEADx Leadership Show, we always say we have to be lifelong learners ourselves, every day we've got to be trying to get a little bit better. And I'm curious, not even so much from the content in your book, but your experience as a boss, as a manager, as a leader over many years in large companies and as a venture capitalist. If you had a new manager, a first-time manager, what would be a piece of advice you would give her to get started right out of the gate?

Cast: Great question. One of the five reasons I found that people derail is you get this great individual contributor, and they get promoted to be a manager, and they continue trying to do it themselves. They over-manage, they micromanage, they don't teach them to fish, they try to fish for their team, and they don't realize that it's literally a transformation of identity to become a manager from being a doer, you have to enable instead of do and it's a nervy concept. When you're good at doing stuff, you want to keep doing stuff. And so the advice I would give that first-time manager is to understand what got them there. What got them here won't get them there, to use the phrase of Marshall Goldsmith. So you have to learn to codify, what you've learned that got you promoted, you should try to codify and teach your team.

Kruse: That's great.

Cast: And enable them to do what you've learned to do, and you know, it's kind of like I think trust and verify, as Reagan said, you want to develop a set of KPIs, key performance indicators, that your team buys into, and then you want to give them the freedom to go out there and hit their marks, and if things go from green to yellow, you'll get a bit involved to coach, and if they go from green to red, you'll get very involved.

Kruse: I like that, changing that situation of leadership based on whether you're still in the green, yellow, or hitting red. And Carter, again, your new book is The Right and Wrong Stuff: How Brilliant Careers are Made and Unmade. You've touched on one of the five common ways people derail, and unfortunately, it's a short format show, so we can't get deep into all of them, but can you touch on these five common ways?

Cast: Yeah, so the one I hit on, I call the Solo Flyer. It's somebody that gets promoted into management and keeps trying to do it themselves and doesn't leverage their team. The other four are, the first one's Captain Fantastic, who's got an ego problem and he alienates people and he bruises them with his sharp elbows. So he has blind spots and he has to sublimate his ego. And that happens a lot in senior managers. They get a degree of success and they start thinking they have all the answers and they stop realizing that what got them there was listening to the front line workers who were closest to the customer. They forget that.

Kruse: And it's probably the higher up you go, the more successful you think you are and the further away you get from those front lines.

Cast: Yeah, and there's great research by Folkman on looking at 360 feedback forms, and as people go up the organization to higher levels, their listening skills get worse. They start thinking they know and people should just follow their direction instead of seeking to understand, so that's another one. A third one is, I call this Version 1.0, and this happens a lot mid-career. We aren't adaptable. We get in a groove, and the groove becomes a rut, and on your point about learning agility, we don't stay fresh. We don't, “Oh, what is AI and its impact on voice recognition and customer service? Cryptocurrency and blockchain, what's really going on there right now and is it going to be regulated more?” You know, big data sets and internet of things, people got to stay curious about all these changing technologies, and the person that derails here gets complacent.

Kruse: You continue some great phrases as a writer and a speaker. I'm not shocked by that, but like you even said, I just love that, you get into a groove but then the groove becomes a rut. And it's great language, and again, with so many of these things, and we're only on number three right here, but it's almost the strength, when you over-rotate, becomes the weakness or becomes the limitation.

Cast: Kevin, I think that was probably one of the biggest themes of the research is what you just said. Many times, these weaknesses are the flip side of really good strengths we have, and we have to explore an overused strength and how it turns into a weakness because we become lopsided in our management profile. So you have somebody who's incredibly analytic and they can make a pivot table smoke when they're doing Excel, but they can't pull the trigger and make a decision because they keep seeking to do more analysis.

Kruse: Right.

Cast: So you've got so many cases of overused strengths becoming weaknesses. A guy named Morgan McCall wrote a book called High Flyers that is a terrific book that talks about overused strengths hurting us, and a guy named Robert Kaplan did a lot of work around overused strengths and in my case, this sort of charming and mischievous trait that I was told I had was overused and it became being difficult to manage by authority figures because I became a smart ass.

Kruse: Right.

Cast: So it's an overused strength that actually hurt me, too. So I think it's a great point you made on that.

Kruse: Now, I'm going to table a question I have, because I want to get through the fourth and the fifth, but you're triggering all kinds of interesting stuff. So you had talked about Version 1.0. What's another common derailer?

Cast: This one's a tricky one. It's called the One Trick Pony, and this is somebody who gets very good at what they're good at, so maybe they're a controller and they're wonderful at closing the books, they do a great job with the audit, they got everybody off QuickBooks, and they want to become a CFO. But they have a narrow band of knowledge and they've gone up vertically through their organization, and they haven't taken lateral moves, and they don't understand how all the pieces fit together in the company. And so they hit a ceiling because of being too narrow.

Kruse: One Trick Pony.

Cast: You know, so for that person, at a certain point in our careers, maybe five to eight years, you become really proficient at something, you should start looking for ways to broaden yourself. Maybe you're in marketing, you should try trade sales. Maybe if you're in merchandising, you should do sourcing for a while. Maybe if you're in FP&A, financial planning and analysis, you should try a job as a financial analyst in a line job instead of as a staff job. So how do you take, not a leap out, but a step out into an area that you can leverage existing strengths but start learning new skills.

Kruse: Great, great. And that brings us to number five.

Cast: The Whirling Dervish.

Kruse: The Whirling Dervish.

Cast: The highest, I have on my website, which is just my name, cartercast.com, there's an assessment tool I built with the CCL, with the Center for Creative Leadership, on derailment, and there are these five derailers and the highest self-rated reason for derailment is the Whirling Dervish, which is you don't deliver on promises because you're overextended and you're juggling and balls start dropping.

Kruse: I guess these are people who just don't know how to say no or don't say no soon enough to opportunities.

Cast: They don't say no soon enough and they don't understand how to effectively prioritize.

Kruse: Right. Prioritization.

Cast: It's really a lot about deciding which activities move the needle and doing first things first.

Kruse: Right.

Cast: And I think in this day and age, we're just clobbered with digital messages and we all feel like whirling dervishes going from one beep and notification to another. It's dangerous.

Kruse: What do you think about this idea, though, on some of these things that you bring up. Are they limitations, are they weaknesses, or is it just an environment misfit? Meaning, you talk about yourself kind of challenging authority and all this, and at some point, you got labeled as tough to work with or doesn't follow my orders or whatever that is, in a big, old-fashioned company, but from what I hear, you might've thrived at Amazon, where they love to debate and you know, with honest, raw emotion ideas and positions. What do you think?

Cast: I think that's a wonderful question. I found three categories of derailers. There are skill gaps, like One Trick Pony needs to gain additional skills to become a CFO from a controller. She has to learn capital asset management, long range forecasting, whatever. There are skill gaps. There are interpersonal vulnerabilities often that are attached to blind spots, like I had. And the third category is what you just said, and I think it's the grand poobah. You're in the wrong context. The culture you're in doesn't fit you. The stage of company, I do a chart for my MBAs with five stages of a company, and I say, “Where should you play, given who you are? Incubate, startup, aggressive scale, growth, or mature phase? Five stages, with your natural personality traits and skills, where should you play?” And you are right, Kevin, I had no right playing in a mature company with my itchy nature. I was perfect for the startup and scale phase.

Kruse: Right, right. Which you eventually did, in…

Cast: Which I wandered my way down to after beating my head against a brick wall for 11 years, yeah.

Kruse: And I think in the book you had mentioned that like some of your MBA students now will say things like, “Oh, I'm going to start my own company,” or “I'm going to go do the tech startup after I do my 10 or 20 years of experience in Fortune 500,” and you obviously, “No, no, no. That's not the right way to think about your career.”

Cast: Yeah, you know, ultimately, and this is how I got to know Dan Pink. I think it always comes down to motives. What gives you energy? In what environment are you in a state of flow, like Mihaly Csikszentmihalyi would say? You know, you're absorbed in an activity and you're really grooving and time flies. If you look at your calendar for a week, which meetings are you excited about going to? If you look at the emails that are in your inbox, which ones do you look forward to opening? Which ones do you open first, and which ones do you groan at when you look at them? When do you raise your hand and say, “I'll take that”? These all give us an idea of what gives us energy and how can we find jobs where more of the activities on a daily basis are around those areas that give us energy.

I had no right being a corporate, I ended up being a CEO for a multi-billion-dollar division of Walmart, and yet, half those activities that I did every day didn't give me any energy. When I'm a teacher and a venture capitalist, 80%, 90% of the activities I do give me energy. So I would say to your listeners, figuring out the activities that give you energy and trying to map those to jobs, it sounds easy, but actually, you've got to be pretty deliberate about it.

Kruse: Yeah, and Carter, I just want to, I think what you just said is so important, and I want to underscore it for our listeners. As I've gotten older, more and more, I think about energy and how to maximize it and what are the activities, the people in my life, et cetera, that bring positive energy. My own sort of aha around this was I had sold a small company I had in the 20s, I was 30 years old, and the bigger company, Kenexa, that had acquired me, they wanted to put me through these psychological assessments, right? So one of them was a sales assessment, how good of a salesperson am I.

Now, I'm 30 years old, and I'm thinking, “Well, I sold my business and I've sold million-dollar enterprise SaaS deals before SaaS was a term.” I'm thinking I'm a great salesperson, I'm going to ace this psychological profile. And they put me through this thing and they come through and said, “Hey, we're going to debrief you,” and they go through and very quickly I saw according to them, I'm a horrible salesperson, like personality was not for sales. And my immediate 30-year-old reaction was defensive and, “Well, this is a stupid assessment and what's the validity behind this,” I just challenged it. And it was very quickly they said, “Listen, it doesn't mean you can't sell. It doesn't mean you can't be successful in sales. It's saying your personality type, it's not natural. It's not where you get energy, where you feel good.”

And as soon as they explained it that way, I mean, I almost realized like, “Yeah, for the last 10 years, I've been pretty miserable because my number one job every day is selling.” Early days, it was 50 cold calls a day. Later days, it's business development. And I realized, that actually is not, even if I can do it, that's not a strength. And the sooner I let other people who love that stuff do it and I focus on other areas, the better. And I think the earlier in our careers that we can learn this, the better, right?

Cast: Amen. And I have the same story. I took an assessment to be the chief marketing officer of Levi's, when I still hadn't woken up to the fact that I should be down in the earlier stages of a company. I took this assessment, and they said, “There's some stuff on this assessment that worries us about your personality as it relates to speed, team play with authority figures,” all this stuff, and they said, “We don't think we should give you this job. You can do the job based on your background, but we don't think there's a fit.” I ended up going to eBay, CMO of eBay. I lasted three months.

Kruse: Wow.

Cast: And I left. I walked out after three months because there was enough hierarchy and it was a big enough organization at that point, all it did was it annoyed me, and it was my fault. It wasn't Meg Whitman's fault. It was my fault because I took the wrong job, given what you just said.

Kruse: So when you got that feedback from Levi's, what did you think? Did you think, “Well, that's a stupid assessment,” or, “That's interesting, but I know what the next rung on the ladder is”? How did you process it?

Cast: What you just said. I had made a mistake. I was a little bit too inflexible. I thought given all the marketing training I've gone through, I should be a CMO. I should be a CMO, and this is the next step of being a CMO. Then when they turned me down, I got the CMO job at eBay, which actually was a bigger and better job at that time, and I thought, well this fits the CMO path that I've been on. So it was, I was working against an assumption I'd had for about 15 years that was an old, faulty, dusty, assumption.

Kruse: Yeah, yeah. This is powerful stuff. And kind of a context for all of this, you know, in your book, you say a lot of people are talking about the strengths-based movement, leading with strengths, reinforcing people's strengths. You say we need to talk about strengths, but also have some straight talk about developmental areas. So give us more advice on this, especially from this perspective of we're trying to develop our team members.

Cast: Yeah. Well, you know, I love the strengths movement. What's not to like about it, right? I mean, we've just been talking about strengths, essentially is putting ourselves in the right context where our strengths will flourish, so I agree with it, but it can't be done at the exclusion of understanding our vulnerabilities and weaknesses and skill gaps.

Kruse: Right, right.

Cast: So it's not either or. It's yes and. You know? And so what I think is really important is make sure you work on a development plan for yourself and get your boss's approval or engagement in it, and I think that development plan should be pretty simple. Maybe it has five items, maybe it has three. One or two of the items should be areas that you have either skill gaps or weaknesses that you're working on. But a couple of the items should be strengths that you want to amplify. New experiences that your boss and your organization's going to give you that will make you even more analytical, even a better salesperson, even more effective as a supply chain manager. So I think the dev plan should be this nice balance of development around gaps or blind spots or vulnerabilities, but also don't forget about development around areas that you're strong to be even stronger.

Kruse: Yeah. I think that's great, and for people who think it's all about the strengths, if you listen carefully to the Gallup work and their interviews, they themselves will say, it doesn't mean you ignore the developmental areas that are going to hold you back. I mean, if there's something that's interfering with the job, et cetera, you do need to address those. It's just try to play to the strengths.

Carter, this has just been a phenomenal conversation. There's so much more good stuff in your book. How can our listeners find out more about your work and your book, in particular?

Cast: Oh, well thank you for asking. I built a website around the book that's just my name, cartercast.com, so you can read about, you can take this assessment, et cetera, and then the book's available for purchase at Barnes and Noble and Amazon and everywhere else, and it's The Right and Wrong Stuff, and my bio on my Kellogg as a professor, if you go and enter Kellogg and my name, you'll see a bunch of the things I've written that are available if you're curious.

Kruse: I love that, and I'm going to wrap up, I like to challenge our listeners to get a little bit better every single day, and you covered so many things that could be our challenge of the day, but the one I want to highlight before we sign out is, listeners, I want you to take a piece of paper and put a couple lines down so you've got three columns, and on the top of one, put “skill gaps.” Across the other one, “interpersonal gaps or developmental areas,” and third, “context or environment,” and have an honest conversation with yourself, what are some developmental opportunities in these three buckets. I think it's a great model for us as we develop.

And Carter, we'll put that link in the show notes and articles everywhere we have, and thanks again for coming on The LEADx Leadership Show.

Cast: Thank you, Kevin. I had fun.

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Kevin Kruse
NY Times bestselling author, Inc 500 entrepreneur, and keynote speaker on Wholehearted Leadership and Extreme Productivity. Download 'How Millionaires Plan Their Day: A 1-Page Tool' at http://kevinkruse.leadpages.co/1page/