Derailers: Why Leaders Fail

Much of the writing on leadership (mine included!) concentrates on the positive stories and helpful hints, partly because it’s human nature to prefer the optimism. However, it’s also valuable to be aware of our blindspots and the traits we have that could potentially derail us in our leadership journeys. Career derailment typically occurs when an executive’s career is going well and should be progressing but it unintentionally fails. I’ve heard that roughly half of executives derail at least once in our careers (!) but given its nature, derailing isn’t widely publicised (unless high profile). 

It’s helpful for leaders to be sensitive to potential derailment of those around us too, especially in our own teams, so that we can offer support. There is some connection to burnout, although that is often caused by external factors wearing us down rather than inherent personality-based behavioural traits we have. The first step in dealing with our derailers is to recognise that we are fallible. And that imperfect human beings can still be amazing leaders. Acknowledging this frees us to learn to manage our derailers. 

Understanding derailers helps us better understand why talented leaders make poor decisions, overlook opportunities, alienate key people, and miss obvious trends, even when we genuinely want to do the right thing. Read more to see how our strengths and derailers are related, explore potential causes of stress, and unpack 11 behavioural traits that can cause leaders to fail. As you read, please reflect on yours, and their triggers, and do reach out to us if you’d like support in managing them on your own leadership journey. 

Two sides of the same coin
Our own potential leadership derailers stem directly from our strengths i.e. they manifest as negative consequences of positive attributes. Our strengths become warped when we’re under stress and pressure, and we don’t see what we’re doing wrong… After all, we’re being ourselves and doing the same things we’ve done successfully for years! So, failure completely blindsides us, even if others spot warning signs. 

Simplistic examples include a confident salesperson becoming overbearing under increased stress, or pressure prompting a careful accountant to micromanage his team. 

And, while derailers emerge under stress, what’s stressful for one leader may not be for another. It’s crucial to build our self-awareness so that we understand what kinds of stress we’re vulnerable to and what triggers our personal derailers. 

Causes of stress
Executives often begin to exhibit our derailers when we are under acute pressure that leads to prolonged periods of intense stress. This extent of pressure is typically beyond the day-to-day challenges at leadership level, which we are likely to have adapted to. Instead the extreme strain could be brought on by combinations of: 

• significant organisational restructuring
  
• a new boss
  
• market downturns
  
• a promotion
  
• joining a new employer
  
• personal challenges such as divorce, death in the family, illness etc
  
• moving to a new country

And, the pressure may be both real and assumed e.g. imagined expectations of a new boss. 

One example of a particularly stressful situation is moving to a new country as a lot can be changing at once. A new language, country culture, market conditions, boss, team, peers, organisational culture, and perhaps business model. On top of this, some executives will have complex personal situations including children and/or a partner also adapting to the new circumstances. 

There is a vicious cycle at play under intense pressure: an initial derailing tendency emerges, which causes additional pressure, leading to other derailment tendencies emerging and compounding the bad situation, before, finally, complete derailment. 

The Derailers
But, our goal shouldn’t be to eliminate our derailers – we can’t. They’re part of our personalities, and have been with us from the start of our careers, probably without serious negative consequences earlier. Our aim should be to:

• understand them, 
  
• determine what causes them to occur, 
  
• and learn ways to manage them i.e. keep them in balance. 

Some of the most effective and successful leaders have multiple derailers – this is to be expected as every trait has a positive side that helps us achieve success as well as a downside. 

Drs David Dotlich and Peter Cairo wrote about derailers in their book ‘Why CEOs Fail: The 11 Behaviours That Can Derail Your Climb to the Top – And How to Manage Them’*. The Hogan Assessments (personality assessments) refer to derailers as the ‘Dark Side’ which can disrupt relationships, damage reputations, and derail success. There is alignment between these approaches although they use different descriptors. Below I describe the 11 together with their twin strengths, in no particular order – the subscales in each heading are from Hogan. As you read the details, please reflect on which are possible derailers for you: 

1) ‘Arrogance’/‘Bold’ with subscales: entitled, overconfident, fantasised talent
This behavioural trait is the dark side of self-confidence i.e. seeming fearless and self-assured. One of the most challenging balances in leadership is between too much confidence and too little – to succeed, we need to have belief in our abilities, but if we start to reinterpret data to fit our world views, we close ourselves off to learning, and resist change. We also become unable to admit mistakes, and can compound them by blaming others. And, we fail to recognise our own limitations. 

2) ‘Melodrama’/‘Colourful’ with subscales: public confidence, distractible, self-display
Charisma and presence are also great attributes to have as a leader i.e. seeming gregarious, fun and entertaining. However, being fond of the spotlight can become overly dramatic and eager to grab attention, which can detract from others’ performance. Showboating can also impair our ability to see what’s really going on. Melodramatic leaders talk big, which can cause elevated expectations, and focus can be scattered as they’ll often say whatever comes to mind in order to impress. 

3) ‘Volatility’/‘Excitable’ with subscales: volatile, easily disappointed, no direction
Passion and enthusiasm are important, especially to inspire others to join us on the journey we wish to lead our business or function on. But, with the highs can come the lows i.e. being easily frustrated, moody or irritable, and we may give up on projects or people. Our mood swings can drive business swings, and unpredictability can drain subordinates who try to adjust. Some signs include people holding back from delivering bad news or broaching certain topics with us, or trying to stay out of our way. 

4) ‘Eagerness to Please’ / ‘Dutiful’ with subscales: indecisive, ingratiating, conforming
These leaders are able to get along with anyone, effortlessly helping others feel at ease. People-focused, they are astute at achieving consensus. But, they can also have an aversion to conflict and contentious debate which leads them to bury opposing opinions and/or unconventional ideas. With this trait, we can struggle to face tough people decisions, be unwilling to defend our people when a customer (for example) challenges them, and avoid opportunities for creative conflict. In our efforts to please everyone, we can lose people’s support and loyalty by agreeing too much and not forming our own opinion that we stand behind. 

5) ‘Excessive Caution’ / ‘Cautious’ with subscales: avoidant, fearful, unassertive
While it’s sensible to look before we leap, prudence as leaders can prevent us from taking action, instead overanalysing decisions or procrastinating, requesting more evidence before we feel comfortable to act. The issue can quickly become (much) worse or the opportunity is long gone, and our indecision and fear of failure has precipitated the failure! Indications that we may be too risk averse include an unwillingness to fire anyone, a preference for small actions with little risk that don’t lead to progress, or an absence of strong opinions or engagement in debate i.e. observing instead of taking action. 

6) ‘Perfectionism’/‘Diligent’ with subscales: standards, perfectionistic, organised 
Having high standards for ourselves and others, and being hardworking and detail-oriented, can be great in business. However, their dark side can lead to us being so wrapped up in the little things that we miss the major developments around us i.e. the big things go wrong. There are some areas where perfection is great, but in many other areas, good enough really is good enough. These leaders are terrified of ambiguity that can’t be resolved by rigorous analysis, and messy and chaotic situations that defy attempts to order them. With this trait, we can have difficulty delegating and can obsess over details. As our stress escalates, we can work even harder to attempt to control the details, tightening our grip, and making things worse and worse. 

7) ‘Habitual Distrust’ / ‘Sceptical’ with subscales: cynical, mistrusting, grudges
It’s good as a leader to be risk-aware: healthy scepticism is helpful. But, when we become overly suspicious, focusing on the negatives, it sends a message of mistrust and people avoid risks under our steely gaze. We second-guess others’ motives, and are constantly on the lookout for deceptive behaviour in others. This makes our direct reports become highly defensive, covering their backs, and causes us difficulties in forging alliances with external people and organisations. 

8) ‘Aloofness’/‘Reserved’ with subscales: introverted, unsocial, tough
Some distance can allow us to be more impartial, insulating us from drama, and giving us a birds-eye view. But, under stress, we can become withdrawn and isolate ourselves from those who desperately need our input or support e.g. hiding out in our offices! We can ignore conflict, hoping it will go away, and our people stop working hard because they get no recognition from us i.e. disconnecting destroys motivation. And, because people have to guess what we think or want, there can be widespread false assumptions and miscommunication. 

9) ‘Mischievousness’/‘Mischievous’ with subscales: risky, impulsive, manipulative
Mischievous leaders have an impulse to break the rules, test the limits and shake things up, which can be great when challenging the status quo, aiming to disrupt an industry as a new entrant, or taking risks. However, behaving impulsively can mean we don’t consider the impact of our actions thoroughly enough. With this behavioural trait, we are easily bored, and like to stir the pot to liven things up. Our adventurous streaks can lead to others questioning our commitment to things we start as we don’t tend to follow through. Acting in the spur of the moment also risks leaving others behind as we don’t take time to win people over. 

10) ‘Eccentricity’/‘Imaginative’ with subscales: eccentric, special sensitivity, creative thinking 
Marching to a different drummer allows us to see things differently, and spot innovative opportunities others can’t see i.e. creativity is a strong advantage of this trait. But in a crisis, we can drive others crazy by proposing yet more wacky ideas, or acting in a way that others find bewildering. Eccentricity can repel others: bizarre, and not in an endearing way, as we’re different just for the sake of it. Clues here include not being able to prioritise as we believe all ideas are critically important, stubbornly going it alone, and/or not being taken seriously as a leader.

11) ‘Passive Resistance’ / ‘Leisurely’ with subscales: passive aggressive, unappreciated, irritated
This duplicitous behaviour trait poses as friendly and cooperative, while we as leaders actually follow our own agendas. We quietly, but stubbornly, resist what others are trying to achieve. We nod publicly and voice that we offer full support, but privately we badmouth the project and/or withhold support. Leaders like this create expectations we don’t meet, confusing and disappointing our people in the short-term and creating cynicism and anger in the long-run i.e. we don’t follow through on public commitments. Teams, alliances and partnerships can fall apart as result of our lip service. 

Wrapping up
Please bear in mind too that companies can be hit by both internal and external shocks i.e. leaders can operate in contexts beyond our control, and our success rests on us, yes, but also the others around us. That’s why we need to build strong, diverse teams, who can offer different perspectives, and together adapt to evolving circumstances. The most senior example of this is the company board, which plays a strong role in reading market signals, and calling on their own experiences, networks and resources to temper management hubris and guide the CEO (and organisation) towards success. Please do reach out to Protagion’s experienced professional mentors and coaches for support in leading your team and organisation to even greater heights. 

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