How to Stop Sabotaging Your Career

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Former Walmart.com CEO Carter Cast discusses the different ways people inadvertently hurt their careers.

718h32tARCLAre you the Captain Fantastic in your office? That’s the guy who knows all the answers and never needs help. Or maybe you’re a Whirling Dervish who tries to take care of everything, all at once. These are some of the archetypes identified by Carter Cast in his new book, The Right and Wrong Stuff: How Brilliant Careers Are Made and Unmade. Cast, a professor of innovation and entrepreneurship at Northwestern University, venture capitalist and former CEO of Walmart.com, explains how smart, talented people sometimes derail their own careers. Cast joined the Knowledge@Wharton show on SiriusXM channel 111 to talk about how to become more self-aware and stop career derailment in its tracks. (Listen to the full podcast using the player at the top of this page.)

The following is an edited transcript of the conversation.

Knowledge@Wharton: The idea for this book came from your personal experience?

Carter Cast: That’s right. I had a bad review when I was in my mid-30s, which was 20 years ago, and was blindsided by the feedback. My boss told me that he no longer wanted me in his group because I was difficult to work with and didn’t follow direction. I ended up being put on ice at the company and was considered non-promotable for about a year and a half. I had to dig my way out of the hole I made. I was embarrassed and didn’t see it coming. One of the reasons I ended up writing this book is to help people so that this doesn’t happen to them.

Knowledge@Wharton: Did you have level of comfort where you were just moving along and doing the job, then you suddenly got hit by this?

Cast: One of the reasons I found that people derail is during transitions. They transition to a new boss, transition into a new job, and they don’t stay flexible and open minded and adaptable. I had a new boss who was much more participative than my old boss, who was more hands off and let me run. I didn’t react well to the new boss’ style.

Knowledge@Wharton: What are some of the most common reasons why people derail their careers?

Cast: The most common reason is an archetype I created called Captain Fantastic. This is the guy with the sharp elbows who bruises you on his quest for the Holy Grail of the corner office. Captain Fantastic has personal issues driven by arrogance, ego and defensiveness. People just don’t want to work with this guy, even though he’s smart and capable. Eventually, when his numbers turn and he doesn’t make his quarter or his year, he finds that no one wants to help him.

“With the rate of change in technology lifecycles, none of us can get complacent with our knowledge.”

Knowledge@Wharton: But more companies are organizing their employees into teams to promote innovation, so being able to get along with others is paramount.

Cast: I think that’s right. The set of interdependencies now is so great with globalization and with so many products having such a technical foundation that you need to have an attitude of we, not me. Captain Fantastic doesn’t have that attitude. That’s the No. 1 reason that people run into trouble.

A close second is this archetype I call Version 1.0, which is someone who gets stuck in their ways and isn’t adaptable to changing circumstances. With the rate of change in technology lifecycles, none of us can get complacent with our knowledge. We have to stay active reading from the thought leaders, reading white papers, going to conferences. We’ve got to stay abreast of all the changes that are happening.

Knowledge@Wharton: Another type you have identified is the Whirling Dervish, who is someone who tries to do too much and gets overwhelmed. Tell us about that.

Cast: I have an assessment on my website where you can see which of these archetypes you fit into, and this is the No. 1 self-claimed archetype. We’re constantly bludgeoned with texts and emails, so I think we all feel like Whirling Dervishes now.

Knowledge@Wharton: What is the most important thing about recognizing your own trouble spots and accepting feedback?

Cast: The most striking piece of research I found is that people who have an inaccurate self-assessment, who don’t have high self-awareness, derail. They get fired or demoted six times more frequently than people that have an accurate self-conception. It’s not about thinking that you’re great at everything. People who understand what they are good at can move around their weaknesses or the fact that they have a vulnerability. People who think they’re good at too many things or have a difficult time facing the music end up failing six times more frequently than those with accurate self-conception.

Knowledge@Wharton: How are these concerns different in men and women?

Cast: The most common reason that men derail is usually they’re Captain Fantastic. It is thinking you have the answers, so you stop seeking the answer. Usually the people who have the answer are on the front line of our business, closest to the customers. You’ve got to get out of your office and talk to those folks and see what’s really going on. Men often suffer because of ego, of thinking they have the solutions without asking.

Based on looking at hundreds of thousands of 360 feedback forms that came in about people, the No. 1 reason women derail is being called nonstrategic, which is ridiculous. There’s nothing inherently more strategic with men than women — I think it’s really a problem with access and visibility. Women get in different roles and rotated into enough roles where they get a vantage point of the business that’s broad enough that they see how the different pieces fit together.

Knowledge@Wharton: How does position in the corporate structure affect behavior?

Cast: Different levels have different derailment tendencies. If you’re junior, the chances you’re going to derail are more likely because you have difficulty managing teams, which is my archetype that I call the Solo Flyer. You want to do it yourself because you’re comfortable doing it yourself or you know you’ll do a good job. That’s not scalable, and your team becomes disempowered, disenfranchised by that.

“There’s nothing inherently more strategic with men than women; I think it’s really a problem with access and visibility.”

Mid-level managers start to run into trouble by being nonstrategic because they haven’t yet had a vantage point of different functions and how they operate and how the whole company is interdisciplinary. In later stages, it’s the hubris. Senior vice president, executive vice president — it’s being too far removed from the front lines and starting to think that you have the answers. It’s that Captain Fantastic archetype that hurts people

Knowledge@Wharton: You also mention that people have blind spots. Could you explain?

Cast: I love reading Joseph Campbell, who wrote The Power of Myth. He said the best way you can understand where you’re headed and how to look at yourself clearly is by journaling, so you can look back at what you’ve written and see the themes that play out on a regular basis — your fears, your vulnerabilities, what you want to do.

But he also said there’s nothing like asking your friends, because those closest to us see us more clearly than we often see ourselves. Go to the folks that care about you, that want to see you succeed and just ask them for honest feedback. “Where do you think I have a developmental opportunity that I need to pay attention to in my career?” If you trust them and they trust you, they’ll tell you the truth. It could be an area that’s a blind spot, like mine was this sort of difficulty with authority figures.

Knowledge@Wharton: If someone has mastered a particular skillset and relies heavily on that at the office, can that cause trouble as well?

Cast: This is a really good question. At Kellogg, we talk about the leadership T. The vertical part of the T is rigor and expertise. The horizontal part is management leadership. A lot of students say to me, “I’d like to become a leader or a manager.” Well, that’s great. That’s the top of the T. But you’ve got to spend time at the bottom of the T to get the credibility and expertise to get to the top of the T.

At what point do you have enough expertise at the bottom to start broadening yourself? If you do it too early in your career, like you try to become a general manager right away, you probably don’t have the expertise to make the right decisions. But if you wait too long, you’re pigeonholed as being a functional expert in one specific area. The advice I generally give is that it takes five years of deliberate practice, if you use the 10,000-hour theory. You should become really proficient in marketing or sales or operations or human resources or finance or whatever in five diligent years, then start looking for opportunities to broaden your understanding of the business. But the biggest mistake I see for young MBAs is they get impatient with their careers, jump around from place to place and don’t establish that bottom of the T.

Knowledge@Wharton: What about young entrepreneurs? A lot of them are fresh out of college and don’t have that leadership quotient, yet they’re trying to build these great ideas from the ground up.

Cast: Entrepreneurs are a different breed. I spend all my time with entrepreneurs as a venture capitalist and teaching two entrepreneurship classes at Kellogg. You have a founder profile for people that are going to be crazy enough to go out there and start something from scratch. There is a genetic component to their passion and belief in their idea, their risk/reward profile and their desire not to be managed by other people, which makes them want to go out there and become entrepreneurs.

Nonetheless, they’re going to have this baptism by fire of realizing they have to learn to be decent managers if their business is going to scale. That’s where it becomes interesting. If they can make the transition from a founder to a true CEO as the company scales, they have to learn a lot of these skills. Some of them make it, like Bezos and Gates and Jobs. And some of them sell their businesses or become the chairman and find a CEO to run it.

“One of the biggest reasons people derail isn’t because they’re not talented, it’s because they’re in the wrong job.”

Knowledge@Wharton: Companies realize that losing employees is an expense that they don’t want to incur. Does that make the leadership more willing to help employees overcome obstacles that could derail their careers?

Cast: My research found the opposite, unfortunately. I found that organizations are very complicit in people’s derailment because we live in the age of the ‘[IRS Form] 1099’ employee, the free agent. It isn’t like when I grew up and IBM gives you lifetime employment. I went to PepsiCo for 11 years and went through a series of developmental training programs before I got my first line job. That day and age is over. You have to take care of your own career because your organization is probably not going to put down a formalized development plan to make you loyal to them.

But what I do say to organizations is, while you’re going through these annual performance reviews that we all hate, make sure that half the time is on development. Don’t make it all rearview mirror about what you did wrong and what you need to improve on. Spend half the time looking forward and saying, “Where do you want to go in your career? How can I help you get there? Where do you have skill gaps? Where do you have developmental needs?” The chances are a lot better that they’re going to stay loyal to you because they know that you care about their personal advancement.

Knowledge@Wharton: What do you tell your students about career development?

Cast: The first thing I say is, get in the habit of constantly receiving and asking for feedback. Don’t wait for the performance review, like I did, to find out that you’re viewed poorly by your manager. The minute you’re done with the presentation, the minute you’re done at a big meeting, ask, “How did that go? Tell me one thing that went well and one thing that I could have done better?”

The second thing I’d say is, if you are in career trouble and you’ve hit a wall, finding a career coach is really helpful. It doesn’t have to be that expensive. You can use them for three or four sessions, and they have a lot of tools you can use to help see yourself more clearly.

Knowledge@Wharton: For employees who are also entrepreneurs, there’s a frustration with moving through the corporate structure to gain experience while wanting to go out there and run a business. How should they develop their careers?

Cast: It gets back to your motives. Some people are motivated by autonomy. Some people are motivated by achievement. Some people are motivated by affiliation. Some people are motivated by a sense of purpose. If you’re motivated by autonomy and achievement, and they are really strong drivers for you, you probably should be doing something at a smaller company or being an entrepreneur. I’m motivated by autonomy, so working inside of Walmart or PepsiCo after a while got very frustrating to me. Try to understand your own motive profile. I talk about that a lot in the book because sometimes one of the biggest reasons people derail isn’t because they’re not talented — it’s because they’re in the wrong job.

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