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How to not let your leadership strengths derail you when things get tough.

Photo by Rishabh Dharmani on Unsplash
History doesn't repeat itself, but it often rhymes.

I worked at Enron for three years until it failed under the weight of lies and accounting fraud, and even I am surprised about the rise and fall of WeWork.

I was surprised because nothing is unique or particularly new for Adam Neumann's (founder and former CEO) fall from grace. You can check the reasons for the rapid rise and fall against the common reasons leaders fail from the aptly named book "WHY CEOS FAIL". And that is why I was initially surprised:

✅ Arrogance - "you're right, and everybody else is wrong."

✅ Melodrama -" you always grab the centre of attention."

✅ Volatility - "Your mood shifts are sudden and unpredictable."

✅ Mischievousness - "You know that rules are only suggestions."

✅ Eccentricity - "It's fun to be different just for the sake of it."

These five immediately jumped out and were at the top of the list for reasons that I can see for why the WeWork CEO failed. Yet how did the board and C-Suite, as Winston Churchill said, " to learn from history... and so repeat it." allow this to happen? The excellent book "The Cult of We" details the collision of forces that explain the rise and fall of WeWork. But I want to explore these leadership traits and derailers in more detail because they are common topics for experienced executive coaches to work with their clients on. A derailer is an overused strength. One developed over time that has worked in the past, and may not serve us so well in the future, crucially as people step up and into more senior leadership positions.

What are the triggers for these derailers? How does a driven, successful business person prevent their careers and businesses from being derailed?

What is the real issue?

When coaching successful executives, I have found, from the C-Suite through senior management to middle management, that many do not receive adequate feedback or confrontation to help them understand their personalities and their impact on those around them. Once they do, they are usually capable of adjusting their behaviours in ways that lead to increased success - creating enduring positive change.

I say usually capable of changing because not everyone cares, especially the delusional leader:

  • The lost cause - will never accept feedback as correct because of a complete lack of insight and self-awareness. They see themselves as pretty close to perfect, and the lost cause is rarely willing to entertain the notion that they might have room to improve.

  • Aware but doesn't care - they are aware of their negative impact on others. Still, they will carry on regardless because they believe their approach and behaviour will help them get what they want. And therein lies their delusion because they draw the wrong lessons from good outcomes. Often their success to date has been despite their delusional behaviour.

To consider an alternative view, you must be willing to consider an alternative version of yourself.

Coaches often work in difficult areas of personal development. If these areas were simple to understand and easy to resolve, the person would not need a coach. They would have simply done it themselves. Often coaching is holding a mirror up and showing the person something they do not want to see and have avoided up to now. Coaching is about challenging assumptions, examining behaviours and habits, overcoming barriers and embedding change and challenge.

Two of the most effective coaching tools to raise self-awareness and confront people about their personalities and the negative impact they are having on those around them as their businesses are:

360 Feedback - the best way to improve your performance at almost anything. I have covered this topic extensively elsewhere. I strongly encourage you to read my article on the ways to seek feedback from those around you.

Psychometrics - Just as there are different types of coaching and leadership styles, there are different types of people and elements to an individual's personality. 'The big five' are considered the key underlying traits that make up an individual's personality. Also referred to as OCEAN, this is a powerful way to help you understand yourself and the people that you interact with. There's no right answer; scoring high or low isn't better or worse. There's no perfect personality.

By understanding the underlying personality traits that can lead to different behaviours, we better understand ourselves and the people with whom we interact.


  • Openness: Measures the degree to which a person likes to learn new things and enjoy new experiences. Openness traits include being insightful, imaginative and independent.

  • Conscientiousness: People who have a high degree of conscientiousness are likely to be dependable, reliable, organised, and disciplined but may be rigid and not like change.

  • Extraversion: Extraversion traits include being energetic, talkative, and sociable. Extroverts get their energy and drive from being with other people, while introverts are self-driven; they get their drive from within themselves.

  • Agreeableness: Assesses the degree to which a person seems warm, friendly, compassionate and cooperative, and traits include being kind, trusting and helpful. In contrast, people with lower levels of agreeableness may be more detached and challenging.

  • Neuroticism: Measures one's predisposition to psychological stress. People that score highly on neuroticism are often less stable under pressure. People with lower scores are usually more secure and confident.

Personality and why it matters in business

There are many personality assessments, often referred to as psychometrics, which help you determine your personality traits. The OCEAN mnemonic and these assessments will help raise your self-awareness. The vast majority of people don't receive adequate feedback to help them understand their personalities. Once they do, they are capable of adjusting their behaviours in ways that lead to increased success.

During a coaching engagement, I will typically use one or both of these tools (360 Feedback and Psychometrics). Because I have written extensively about Feedback previously, I will introduce the Hogan (Psychometric) Assessment here. We will delve into these derailers and why it is important to understand yours.

The Hogan assessment is based on the two views of personality:

  1. INSIDE OUT - your identity. The "you" that YOU know.

  2. OUTSIDE IN - your reputation. The "you" that OTHERS know you to be.

This distinction has important implications for transparency and authenticity. Reputation is more useful than identity when understanding others and their behaviours. The Hogan Assessment provides a unique insight into the depths of personality and cognitive reasoning, which can have strong implications for performance and development.

Everyday Leadership

The Hogan Personality Inventory (HPI) is a versatile tool that focuses on normal personality traits that describe how we relate to others when we are at our best. The tool uses scales such as the degree to which a person:

  • is calm and composed,

  • appears talkative and socially self-confident,

  • seems organised, dependable and thorough,

to address different components of leadership performance. We all can change our typical behaviour but,

  1. We need to know what to change,

  2. We must want to change it,

  3. We need to know how to change it.

This tool provides deep insights for my clients that we use to help direct our work together.

But there is more. We often aren't operating at our best. This leads us to the Hogan Development Survey (HDS), often referred to as the "Hogan Dark Side".

During times of stress or when under pressure

The HDS describes the dark side of personality - qualities that emerge in times of increased strain and can disrupt relationships, damage reputations and derail people's chances of success.

The typical person will have approximately three high-risk derailers. Therefore, it is essential to realise it would be highly unusual not to have some interpersonal behaviours that adversely affect your performance and reputation at work. Most commonly, they will emerge during periods of heightened stress. The tool pinpoints potential problem areas by raising awareness of the triggers, such as the situations that bring out the worst in us:

  • Working to a tight deadline,

  • When Short staffed,

  • An operational mistake occurs,

  • Conversations with a difficult client or team member

  • Last-minute changes to requirements.

Or the types of people whose actions might be a source of frustration to you. Their actions may arise from their default position based on their personality type, and the traits hardwired into them. These people are usually well-meaning, and they aren't necessarily intentionally pressing your buttons to cause you grief and angst.

It's difficult for busy people to take a step back and realise that their behaviour might be causing problems. The Johari Window is a compelling visualisation of what these tools are attempting to do:

  • Known by self/known by others - open/free area (top left)

  • Known by self/unknown by others - hidden area (both left)

  • Unknown by self/known by others - blind spots (top right)

  • Unknown by self/unknown by others - unknown area (bottom right)

Johari Window model

The aim is to increase the area of the first box and hence minimise the sizes of the other three. 360 Feedback and Hogan help us achieve and increase our chances of success with a new opportunity or deal with a problem, challenge or obstacle.

Photo by Milada Vigerova on Unsplash

Change isn't easy. It takes a great deal of self-reflection and the courage to hold the mirror up to one's face and take a good look. To proactively and regularly seek feedback and act upon it.

But leadership isn't about taking the easy option. It is about doing the small things that make a difference, influence others and make life at work better.


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