Understanding Managerial Derailment

What causes promising executives to underperform, and how can organisations intervene in time?

Date Posted

6 Jan 2011


Issue 9, 14 Jun 2011

Although considerable efforts have been spent on leadership development research exploring the reasons for success in managerial or executive roles, about half of all managers nevertheless fail. This suggests that a more holistic perspective to understanding leadership is needed, one with a greater focus on understanding why leaders fail.

The term “derailment”, drawing on the metaphor of a train coming off the track, is commonly used to refer to talented managers who enjoyed much success early in their career but then have their advancement involuntarily stalled, or are demoted or fired when they fail to perform to expectations. In essence, derailment indicates a lack of fit between an individual and the evolving demands of the job and the organisation. It is not the same as “plateauing” or voluntarily deciding to opt out of further advancement.

Derailment is of concern to any organisation as the consequences can be considerable, especially at the executive and senior management levels where the impact is greater. Such adverse consequences include: not meeting organisational outcomes, loss of organisational reputation, breeding of dysfunctional cultures and irresponsible or unethical behaviours, as well as the decreased psychological well-being of those adversely affected by derailed managers.


There are four key dynamics leading to derailment:

1. An Early Strength Becomes A Weakness: The very same skills, characteristics and qualities that enable an individual to excel and enjoy success early in his career may become liabilities when he reaches managerial positions and does not develop new skills to balance these early strengths that may no longer be adequate in addressing new job demands. A diligent, conscientious, task-focused individual contributor who is accustomed to achieving results independently may find it harder to build relationships and work through teams or subordinates as he advances up the organisational hierarchy.

2. A Flaw Eventually Matters: Everybody possesses shortcomings or undesirable qualities; for managers, commonly cited ones include arrogance, narcissism, passive-aggression and scepticism. It is estimated that most executives have two to three flaws, which may only surface after a period of prolonged interaction. Some flaws may initially be compensated for by other personal strengths but then become less acceptable as the individual is promoted to higher levels of responsibility. For example, a manager who is intellectually sharp and results-oriented, but at the same time, is arrogant, short-fused or abrasive might be identified as someone with long–term potential based on his strengths. However, his lack of interpersonal skills may limit his effectiveness in managing teams and working through people to deliver results in more senior positions.

3. A Flaw Surfaces Under Extreme Or Unexpected Challenges: A manager may face unexpected challenges brought by changes in the organisation’s operating environment (such as economic downturns, crisis situations or legacy problems within the organisation), causing deficiencies to surface under pressure.

4. Becoming Victims of Their Own Success: Managers who enjoyed great success early and easily may develop an unrealistic sense of superiority and infallibility which affects their judgement and receptivity to alternative ideas or feedback from others. Threatened by the possibility of failure, some managers may resort to tried and-true but ineffective solutions rather than embarrass themselves by experimenting with new strategies that may fail. As a result, they fail to adapt to meet the evolving demands of complex new situations.

Lack of interpersonal skills may limit effectiveness in managing teams and working through people to deliver results.


The derailment dynamics described imply an interplay of situational and individual factors: managers typically possess some individual qualities that put them at risk for derailment, and these are most likely to surface in stressful situations. Situational factors that contribute to possible derailment occur at three levels – organisation, job and person.

Organisational Dynamics

Organisational cultures set the context for success and define what qualities are considered strengths or weaknesses. Hence, derailment qualities vary from organisation to organisation, context to context.

In addition, organisations with dysfunctional cultures, those that are intolerant of failure, or which have unbalanced reward structures that focus on outcomes regardless of processes, are more likely to encourage the display of dysfunctional behaviours that are linked to the likelihood of derailment.

Furthermore, success at different levels of the organisational hierarchy requires different behaviours, skills and perspectives as job responsibilities shift. When there is a lack of proper succession management, managers are more likely to find themselves being promoted to jobs for which they are not prepared in terms of experience and competence.

In particular, young talents who are fast-tracked may be at higher risk of derailment. Despite assuming positions of formal authority, they may have yet to develop the necessary knowledge, interpersonal and communication skills, emotional maturity, informal relationships and resource networks that would allow them to manage others effectively.

Furthermore, organisations often require managers to deal with transitions, such as a change of role or assignment or a new supervisor. While these challenging transitions contribute to skill-development by building a broader base of experiences, difficulty in managing the demands of a transition has been a strong predictor of derailment.

Job Dynamics

Derailment implies a misfit between a manager and his job. In broad terms, the manager’s job could be described as getting results through other people. At lower and middle managerial levels, the focus is on providing task-based leadership and sound technical skills to enable one’s unit to complete tasks and obtain results efficiently. Hence, those who derail at this level tend to lack these job-critical qualities. Managers who have poor interpersonal skills that prevent them from establishing good working relationships with their supervisors or subordinates are also likely to derail.

Young talents who are fast-tracked may be at higher risk of derailment.

Higher up the organisational hierarchy, a successful manager has to develop a greater repertoire of skills in order to respond to the evolving demands of the job, such as developing and promoting a vision, recruiting and retaining talented people and motivating a team. Managers have to effectively garner support and resources for their initiatives. Those who do not possess the necessary intellectual skills such as strategic thinking and ability to make high quality decisions, and the skills or willingness to adapt will face difficulty coping with the demands of working within a larger sphere of diverse functions, and a fast-paced and dynamic environment.

Managing strong teams and working well with others are key aspects of successful managers. Thus, managers at risk of derailment are those who are unable to build, direct and motivate their team, or are unable to teach and develop their team. Managers lacking the necessary interpersonal skills to build and maintain relationships, resolve conflicts or establish consensus across boundaries may be at risk of derailment as their job responsibilities become ever more complex and dependent on teamwork across boundaries.

Personal Factors

Personal circumstances may inadvertently lead to derailment at work. Some individuals lack the passion for managerial roles but accept them as the only way to advance in their careers, while others no longer see meaning in their work. A lack of commitment, coupled with inadequate managerial skills, may eventually lead to performance problems and derailment.

Stress and fatigue – the result of unfamiliar and more demanding job responsibilities as one moves up the organisational hierarchy – are also prime reasons why people underperform or behave in counterproductive ways. An individual’s life-stage and level of maturity is another factor that may result in challenges being faced at work, and increase the likelihood of derailment. Other major events in one’s personal life, such as family-related issues or a major illness, could also have a temporary or long-term impact on performance.


Research provides insight on how managerial derailment can be minimised.

1. Consider potential derailment factors in the selection of talent

Current selection processes typically focus on evaluating applicants against a list of organisational- and job-relevant competencies. Emphasis should also be given to overplayed strengths, significant limitations, or other personal qualities, such as inability and unwillingness to adapt and other key derailment factors. The assessment process should seek to have a holistic understanding of the strengths and limitations of the applicants and consider the extent/ severity and likely impact of these flaws in selection and promotion decisions. Consideration should be made of the individual’s self-awareness (or lack of) and the likelihood of any flaws being overcome over time with the right development interventions.

2. Have a holistic leadership development approach that helps managers identify and manage their risk of derailment

Leadership development has traditionally focused on exploring what makes leaders successful. This may well be inadequate. It is important to take a holistic approach that helps managers be aware of their own shortcomings and derailment risk factors so that they can better manage their own behaviours and personal development.

Furthermore, research has consistently shown managers to be less aware of their own risk of derailment than others perceive. Tools such as self-assessment questionnaires and 360-degree surveys can help managers become more aware of their own potential derailment factors, and development interventions such as coaching, action learning and targeted on-the-job assignments with appropriate feedback and self-reflection are useful in helping managers address their own shortcomings. In addition, when individuals are faced with difficult personal circumstances, it is important for both managers and supervisors to recognise the potential negative impact on performance, and also for the organisation to be supportive of managers in such situations.

3. Design appropriate on-boarding programmes to manage transitions

Successions are significant transitions that may become tipping points leading to derailment. Hence, a better succession process would help organisations minimise potential derailment among its managers. More work could also be done to design and implement relevant on-boarding programmes for managers in new roles, to help them understand the current and future job demands, acquire the necessary skills, and provide them with the necessary support and resources during career transitions. For example, challenging assignments could be better designed or the individual could be given greater support, so that there are more positive outcomes for the individual and, at the same time, a lower risk of derailment.

4. Better manage and develop young, fast-tracked managers

In the Singapore Public Sector, a sizeable proportion of young, fast-tracked managers are identified as potential public sector leaders early in their careers. Such managers may be at risk of derailment if they become victims of their initial career success. A more deliberate focus may be needed to help these managers be self-aware and adaptable so that they understand the potential derailment risk, and work towards developing greater leadership effectiveness in order to improve their likelihood of succeeding as public sector leaders in the longer term. In addition, though talented, the relative youth of these managers may mean that they require specially-tailored developmental opportunities to compensate for their lack of on-the-job and life experience necessary to be effective in managerial roles in diverse workplaces and complex situations.

Research has consistently shown managers to be less aware of their own risk of derailment than others perceive.


Most research on derailment relies on post-hoc explanations provided by the colleagues of the derailed manager. A key limitation of such a methodology is that people’s perceptions of the manager may be biased by the fact of his derailment. Thus, longitudinal studies of managers may help to provide another perspective on the qualities that are most closely associated with derailment. Furthermore, since most findings are based on studies in western cultures, it would be useful to tease out the most relevant situational dynamics and individual qualities that tend to lead to derailment in the unique context of the Singapore Public Sector.

This article is based on the findings of a research study undertaken in 2010 by Khoo Ee Wan and Caithlin Tham of the Centre for Leadership Development, Civil Service College. The full research report, together with the references, can be accessed at


Khoo Ee Wan is Senior Consultant (Psychologist) in the Centre for Leadership Development in the Civil Service College. The Centre provides leadership assessment and development services that support the Singapore Public Service in developing a pipeline of talent that are inspired to lead and drive change.

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