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How Brilliant Careers Are Made — And Unmade

by Carter Cast

Everyone has blind spots and weaknesses. By identifying and addressing your own challenges, you can accelerate your career.

HAVE YOU EVER WONDERED WHY some careers flourish, while others stall? ‘Career derailment’ occurs when an individual previously deemed to have strong potential is fired, demoted or plateaus below expected levels of success. According to statistics, somewhere between 30 and 67 per cent of leaders involuntarily derail at some point in their career.

Not surprisingly, career derailment carries high costs: The direct and indirect cost to organizations can be more than 20 times the derailed employees’ salaries. Given the stakes involved for individuals and organizations alike, I recently set out to pinpoint the major causes of career derailment. In this article I will share key findings from the research, lay out the behaviours that can stall a career and offer remedies to help people avoid derailment.

Career Derailment 101

First and foremost, career derailment does not indicate a lack of managerial talent. Instead, it often afflicts talented managers who are either unaware of a debilitating weakness or interpersonal blind spot — or are arrogant enough to believe that the rules don’t apply to them.

As part of my research, I conducted extensive interviews with three leadership consulting firms: the Centre for Creative Leadership, the Korn Ferry Institute and the Hay Group. All three indicated that organizations prefer to focus on the positive and don’t even like to discuss peoples’ negative qualities. The problem is, these personal weaknesses often override an individual’s strengths. Following are five major career derailers that every leader should be aware of.


Researchers agree that this is the most prevalent and damaging derailer. Stuart Kaplan, the former global chief operating officer of Korn Ferry’s leadership and talent consulting practice (now director of organizational development at Google) put it this way: 

“As you progress [in your career], your relationships with others are more important than your knowledge of and relationship with data. This need kicks in as you move into middle and upper management. It’s a mindset change. You have to let go of having the answer and embrace the relational world. It becomes less about competencies and more about trust.”

To examine this derailer more closely, I broke it down into two categories: relational issues and dark-side personality dimensions. On the relational front, Korn Ferry analyzed a tremendous amount of data from its 360-degree feedback instrument (VOICES®) and found a total of 19 negative behavioural characteristics that reliably correlate to job performance flame-out. Ten of them are related specifically to relational issues. The five most common are, in descending order: defensiveness; lack of composure under stress; insensitivity to others’ feelings; excess ambition; and arrogance. Defensiveness leads the way in terms of career damage because it often suppresses one’s ability to learn and develop.

Defensiveness leads the way in terms of career damage because it often suppresses one’s ability to learn and develop.Tweet this

Looking at the second category, dark-side personality dimensions involve dysfunctional dispositions that are associated with failure as a manager. Psychologists Joyce and Robert Hogan have conducted extensive research on derailment resulting from personal factors and created an inventory assessment tool that managers can take to test for these dimensions. David Dotlich and Peter Cairo put the Hogans’ model into practice with their own tool, the CDR International Derailment Report, which they have administered to thousands of managers and executives. In doing so they have confirmed the accuracy of the Hogans’ dimensions. In Why CEOs Fail, they write:

“Many leaders sabotage themselves, albeit unconsciously. We’ve found all leaders are vulnerable to 11 derailers— deeply ingrained personality traits that affect their leadership style and actions. Odds are that you possess at least one of these traits.”

Dotlich and Cairo’s 11 derailers are as follows:

  • ARROGANCE: You’re right and everybody else is wrong.
  • MELODRAMA: You always grab the centre of attention.
  • VOLATILITY: Your mood swings drive business swings.
  • EXCESSIVE CAUTION: The next decision you make may be your first.
  • HABITUAL DISTRUST: You focus on the negatives.
  • ALOOFNESS: You disengage and disconnect.
  • MISCHIEVOUSNESS: Rules are made to be broken.
  • ECCENTRICITY: It’s fun to be different just for the sake of it.
  • PASSIVE RESISTANCE: Your silence is misinterpreted as agreement.
  • PERFECTIONISM: Get the little things right even if the big things go wrong.
  • EAGERNESS TO PLEASE: Winning the popularity contest matters most.
According to Dotlich and Cairo, most managers possess at least two or three of these derailers. This statistic might seem alarming, but it needn’t be. The unknown enemy is the most fearsome. By understanding our own derailment propensities, we can address them and mitigate their potential to cause trouble.


People who suffer from this derailer tend to do at least one — and sometimes all — of the following:

• THEY OVER-MANAGE. Those who over-manage don’t empower their team members and are over-controlling and meddling. As a result, team members find their efforts thwarted and can lose their sense of autonomy and their desire to take the initiative. Those who over-manage are also poor delegators. Because they were often effective individual contributors, they tend to revert to that behaviour and try to do the work themselves.

• THEY FAIL TO BUILD AND LEAD THE TEAM. These leaders don’t communicate business priorities or provide the necessary strategic context for assignments, so their team members fail to understand how their work fits within the overall strategy of the team, the department or the organization. They also find it difficult to resolve interpersonal, resource-allocation or workflow/process-related problems within the team in a timely manner, reducing its effectiveness, and they do a poor job of developing the functional and managerial skills of their direct reports.

• THEY DON’T MANAGE THE TEAM’S CONTEXT. Managing team members one-on-one isn’t the same as managing a team. Managing a team means also managing the team’s context, which entails: 
1) Scanning the competitive environment and making adjustments to strategy based on an ongoing assessment;
2) Lobbying for and securing resources for the team;
3) Ensuring strategic and project alignment with other internal functions; and
4) Ensuring that team objectives, goals and key performance indicators (KPIs) are clear — and are met.

Those who over-manage don’t empower their team members and are over-controlling and meddling.Tweet this


Almost two-thirds of managers who have derailed were described as being ‘unable to change or adapt’. As people rise through organizations and business situations become more complex, adaptability becomes increasingly important. With additional responsibility, more constituencies and political nuances must be managed. As my colleague, Kellogg Professor Kevin Murnane puts it: “As you progress, you need to move from the technical to the interpersonal and from certainty to ambiguity.”

This derailer can be triggered by three things:

• CHANGING CIRCUMSTANCES. The most common reason for derailment here is that a person gets promoted into a new position and doesn’t have the requisite skills or hasn’t taken the time to understand the job requirements — and continues to act and behave in the same manner as before being promoted. A common issue after promotion is the difficulty of making the mental transition from being a ‘technical manager’ to a ‘general manager’ and moving from ‘me’ to ‘we’. Some people also have great difficulty understanding and accepting fundamental shifts in the macro environment and making the necessary adjustments.

• OVER-DEPENDENCE ON AN ADVOCATE. Another common reason for derailment within this category is over-dependence on a previous boss or advocate. People frequently struggle when they lose their old boss and gain a new one who has a different agenda and management style.

• PERSONALITY TRAITS. These include not seeking input or being unable to take direction from others; being fearful of change (especially of appearing inept); having narrow interests; lacking curiosity; and preferring the status quo, even when faced with new challenges that necessitate a change in approach.


This derailer can be broken into three components:

• OVER-DEPENDENCE ON ONE SKILL. This means relying on the same skill or small set of skills to get any job done and not recognizing the importance of a broadened skill set, and it often comes with a bias for one’s functional area of expertise. The old adage, ‘If all you have is a hammer, everything looks like a nail’ comes to mind. For example, a chief financial officer trying to pin a return on investment to all projects, even those that are exploratory or conceptual; or an enterprise sales manager saying, ‘Selling is selling; I don’t need to understand how our new client software portal works’.

In the book Potential — For What?, the Hay Group lists such narrowness as a critical derailer: “A narrow and short-sighted emphasis on immediate results and/or technical expertise — this is the opposite of lateral thinking and taking a broader view.” All things change, and one of the requirements for higher-level management and career fulfilment is broadness and diversity.

• BEING NON-STRATEGIC. This often takes three forms:

1. Being a whirlwind of execution and not pulling back to examine and understand the strategic context surrounding the work. Given the propensity for this, when I worked at I frequently urged my team to remember to ‘zoom in’ or ‘pull back’;
2. Being too technically oriented, overly concerned with project details, getting mired in the tactics of the business and losing touch with its over-arching objective; and
3. Lacking a holistic understanding of how the pieces of the business fit together — not grasping the value chain, the process or activities by which a company adds consumer/customer value.

• HAVING A KEY SKILL DEFICIENCY. This issue concerns not having a key skill necessary to be successful in a position. Some of the causal factors for this are: counting backwards to retirement and not taking on new challenges or learning new skills; younger managers suffering from general inexperience; lacking technical or functional skills; being new to the job or function and also not being interested in self-development.


This last derailer is an insidious one. When managers cannot be counted on to deliver on commitments, they lose their personal credibility and co-workers slowly but surely back away and avoid working with them. Following are five reasons for poor follow-through. 

• POOR PLANNING AND ORGANIZATIONAL SKILLS. People suffering from this derailer are often disorganized and are not detail oriented, which can lead to unmet commitments.

• TROUBLE PRIORITIZING WORK. Effective managers are able to differentiate high-impact work from busy work and prioritize their time accordingly. They use various heuristics to prioritize, plan and execute their work. An affliction from which ineffective managers suffer is what I call ‘working in response mode,’ wherein
they allow interruption after interruption to impede their progress on important projects by responding, like Pavlov’s dogs, every time a text or email message comes in over the transom.

• BEING A PLEASER. People who have trouble delivering on promises are often pleasers who never say ‘no’ to a request for fear of disappointing their co-workers. As a result, they over-commit and under-deliver.

• NOT UNDERSTANDING DUE PROCESS. In my experience, managers who execute poorly often lack an understanding of the due process required inside their business unit or company. They tend to have a naive or inadequate understanding of the action steps, the work flow, the functional and cross-functional dependencies, and the necessary stakeholder approvals required to complete an initiative inside their company. As a result, they assume they can accomplish activities or projects in an unrealistic time frame.

• SUFFERING FROM GRANDIOSITY. People who suffer from grandiosity often are creative, curious, highly conceptual people who are spirited and full of big ideas. When this trait goes into overdrive, however, their strengths can become weaknesses. They become enamoured of their game-changing, high-concept ideas and are distracted from following through on the mundane tasks or projects for which they are accountable.

Derailment Remedies

All positive change — whether becoming a better leader, learning to be more adaptable, thinking less narrowly or improving follow-through skills — begins with self-awareness. This trait is mission critical. A lack of self-awareness is the single best indicator of an individual’s impending derailment. For those who want to improve their self-awareness and proactively tend to their blind spots, I recommend the following.

SEEK 360-DEGREE FEEDBACK FROM CO-WORKERS. A handful of organizations do a fine job of administering, interpreting and coaching managers and executives through some type of multi-source assessment. I urge everyone — regardless of level — to go through this type of assessment process.

GAIN A DEEPER UNDERSTANDING OF YOUR BLIND SPOTS AND SELF-DEFEATING BEHAVIOURS. Although none of us likes the prospect of hearing about, examining and addressing our areas of personal vulnerability, there is no better way to improve our performance. The Hogan Personality Inventory and the Hogan Development Survey offer a rich set of tools to understand bright-side and darkside personality traits.

GAIN A DEEPER UNDERSTANDING OF YOUR ‘STRENGTHS IN OVERDRIVE’. Do you know the circumstances in which you overuse your strengths? Let’s say one of your strengths is ‘determination’: You are widely known as a person who works hard and doesn’t stop until the job has been successfully completed. Think of what happens when that strength goes into overdrive — when you offer too much of it. Perhaps your determination turns into pushiness. Then think about the challenge behaviour — the balancing behaviour you’re leaving out. So with ‘pushiness’ you might be missing ‘patience’ or ‘deliberation’.

Given your determination, do you have a bias against people who demonstrate great patience and are deliberate? Perhaps you tend to associate these traits with being ‘lazy’ or ‘slow-moving’. The key here is to examine the flip side of your biggest strengths. By doing so, you can uncover behavioural areas that may be
holding you back.

SEEK COACHING AND COUNSEL, ESPECIALLY DURING TIMES OF TRANSITION. When I interviewed Smruti Rajagopalan, an organizational design and talent management consultant at the Hay Group, she stressed the importance of self-awareness and self-management during times of change. Behaviour is a function of a person in a situation, she explained, and blind spots often act as derailers because they cause individuals to misjudge situations and their approach to emerging challenges.

This is particularly true during times of change: A new job or assignment, new boss or other wildcard thrown into the mix can heighten derailment risks. Difficulty adapting to changing circumstances — especially a job change involving a new assignment or a promotion — can often derail promising careers. People perform well when there is a match between their capabilities and the requirements of their job. When that match gets out of balance, they struggle.

While working with both middle and senior level managers attending the Kellogg School’s continuing education program, I have asked hundreds of program participants, ‘When you were promoted or transferred into a new assignment, how many of you had a clear understanding of the skills required and the success factors of your new job?’ Only 10 to 20 per cent of people raise their hands. Then I’ve called on people who did raise their hands, asking them how they went about understanding the job requirements and success factors of their new job and trying to create a smooth transition into their new role.

They have all reported taking one or all of the following actions: First, taking the time to be crystal clear on what their new boss wanted, asking essentially, ‘What will I have accomplished in two or three years to make you say I did a great job in this role?’ From that conversation, they made a list of the three to five key deliverables and then worked with their boss to establish key performance indicators for each. Their goal was to be crystal clear on what success looked like.

Second, if the new boss wasn’t able to provide clear direction, they developed their own goals and objectives, with clear success metrics and then ran them by him/her to ensure alignment. Third, they sought advice from other employees who had gone through the same or similar transitions, asking about challenges in the transition and what to watch out for. What did they learn? What caught them off-guard? Which other departments, functional groups and resources were critical to their success?

What three pieces of advice would they offer? Then, in the early stages of a job transition, they checked in with the boss on a regular basis — weekly or bi-weekly — to make sure they were aligned on what was important to accomplish and make sure they received ongoing feedback.

BE EMPATHETIC AND COMPASSIONATE — AND STAY HUMBLE. One of the best ways to avoid derailment is to be ‘other oriented’ by practising empathy and compassion. When you find yourself in a charged situation with a peer, ask yourself, ‘Why might this person be resisting my proposal?’ ‘What are her objectives, and how might I help her achieve them while still adhering to my own goals?’ Above all, practise humility. Staying humble is important because the leading cause of interpersonal issues is arrogance.

EMBRACE THE SHIFT FROM MANAGING SELF TO MANAGING OTHERS. Making the shift from being a ‘doer’ to managing through others is an enormous transition that is not always easy. When we’re good at something, we like to keep doing it. We see the tangible progress and receive the rewards, so we’re naturally reluctant to change our approach. In Becoming a Manager, Linda Hill discusses the importance of the mindset shift that occurs in this transition from being a specialist to an orchestrator. She writes that this shift literally involves a transformation of identity. To be successful, managers must not only learn their job requirements but also cultivate self-reflection in order to motivate others.

In closing

Your career is not a foot race. It is long. No one — you included — will remember if you reached vice president by age 35 or age 39. So, take the time to get really good at something; that’s your bargaining chip, your career leverage. And by all means, take a lateral move if it’s in a critical path area that’s important to understand.

Always remember: You will only go as far as your blind spots allow. Do whatever you can to increase your self-awareness and reduce the career-limiting effects of blind spots. The fact is, each and every one of us has derailment propensities. To understand them is to empower ourselves to manage past them. The best news of all: By identifying and addressing your own issues and challenges, you can accelerate your career. 

Carter Cast
is the Clinical Professor of Innovation and Entrepreneurship at the Kellogg School of Management, a venture partner at Pritzker Group Venture Capital and author of The Right (and Wrong) Stuff: How Brilliant Careers are Made — and Unmade (PublicAffairs, 2018). He is the former CEO of and has held senior management positions at PepsiCo and Electronic Arts.

This article appeared in the Fall 2018 issue. Published by the University of Toronto’s Rotman School of Management, Rotman Management explores themes of interest to leaders, innovators and entrepreneurs.

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