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Are You Destined to Repeat Leadership Mistakes?

It's likely to happen. Those words you were determined never to say come out of your mouth. And immediately, you think to yourself. I really do sound like my parents! Is that good or bad? It only makes sense that the leader you become in the workplace is influenced to some extent by your experiences and those you admire. Not surprisingly, evidence suggests that personality traits and virtues also significantly influence behavior, especially when you have the freedom to make choices. Let's get clear on what this means. Self-understanding is essential to breaking leadership bad habits. And the bad habits of leadership that we have all witnessed or engaged in are not destiny. An inside-out approach to leadership development is essential for breaking bad habits. Here are four attributes quietly influencing how you lead and practical steps to enhance self-awareness.

Attribute 1: Leadership personality traits and habits

Clear connections between habits and leadership personality traits exist. A leadership study across many different business sectors found that follower perceptions of leader personality significantly correlate to leader behaviors that moderate organizational engagement and performance.

The most widely accepted trait framework is the Five-Factor Model. It presents that openness, conscientiousness, extraversion, agreeableness, and neuroticism as the building blocks of personality. These factors are a causal force on patterns of thought, feelings, and actions.

The American Psychology Association describes the five factors as:

  • Openness - Open to new experiences from a visual, cultural, or intellectual perspective.

  • Conscientiousness - Reliable, efficient, responsible, and hardworking.

  • Extraversion - Talkative, outgoing, sociable, and openly expressive.

  • Agreeableness - Cooperative and unselfish.

  • Neuroticism - A lack of emotional predictability and a tendency to struggle with emotions like anxiety.

Personality assessments combined with executive coaching are an excellent way to get subjective and objective feedback on personality traits and leadership habits. However, not all assessments that measure personality are equal. In addition to understanding the cost and time involved, it is crucial to consider the assessments:

  • Degree of reliability (i.e., consistency)

  • Validity (i.e., the accuracy of interpretation)

  • Fairness (i.e., equivalence across different populations)

  • Type of feedback (group norms or self-reported)

  • Education requirements to interpret the results

There are many different aspects of personality and trait assessments. Here are four examples:

  1. 16PF (PSI Services): The 16PF Questionnaire assesses global and primary factors. Global Factors: Extraversion, anxiety, tough-mindedness, independence, and self-control. Primary Factors: Warmth, reasoning, emotional stability, dominance, liveliness, rule-consciousness, social boldness, sensitivity, vigilance, abstractedness, privateness, apprehension, openness to change, self-reliance, perfectionism, and tension.

  2. DISC Temperament Inventory (Wiley): Measures a person's temperament, the foundation on which personality forms. The DISC measures dominant and recessive temperaments, including driving, influencing, stabilizing, and conscientiousness.

  3. Hogan Challenge (Hogan): Measures 11 common dysfunctional patterns of interpersonal behavior. To evaluate how a person will perform during times of stress and conditions of uncertainty. To aid personal development by identifying behavior patterns that may be derailing tendencies. To inform leaders preparing for or undergoing significant change, for individuals experiencing performance issues, and for leaders whose personality characteristics interfere with their performance.

  4. Personality Vector Analysis (Bartell & Bartell): A snapshot of personality, current growth/development, and vector/valence, measuring a person's natural influence through a task/output approach or a people/process orientation. Very useful in building synergistic teams.

Attribute 2: Leadership virtues, character, and habits

A leader's virtues and values are foundational attributes to effective leadership. Aristotle considered virtues a habit or disposition to think, act, or feel in the right way that is not deficient or in excess and toward a good goal. Virtues are a part of an individual's distinctive character that influences personal values.

In a study involving 2,000 manufacturing companies, researchers discovered that a leader's character had a more significant positive impact on organizational performance and quality than management control processes.

Using an assessment like the Character Strengths Survey from the VIA Institute is an excellent place to build self-awareness about your assumptions and beliefs. The VIA has been completed by over 15 million people globally, and all scales have satisfactory reliability.

The free version of the VIA Character Strength Survey provides insights into character strengths which are described as:

  • Values in action or positive traits for thinking

  • Feeling

  • Behaving that benefit the leader and others

Attribute 3: Leadership experiences and habits

Past events shape the experiences you have today. The positive and negative consequences associated with these past events have the most significant impact on influencing your future behavior. Consequences increase or decrease patterns of behavior, creating habits.

Consequences from events you observe also influence your attitude and actions. According to self-perception theory, you infer a response when put in a new situation. This is why when you are served a meal and see other people's reactions to taking a bite can become anxious to take a bite.

Here are a few questions to improve your self-understanding of the experiences and observations influencing your leadership:

  • What do you like about the way you have been led?

  • What leadership mistakes would you not want to repeat?

  • Who is a leader you have admired? Why?

Attribute 4: Leadership purpose and habits

Any path you take will get you where you are going if you don't know where you are going. A serious threat to achieving success and significance is not being deliberate about your purpose. Living without a vision for the future is not a great approach if you want to make the most of your life and avoid repeating bad habits.

Ask yourself the following two powerful questions:

  1. What do I want to be remembered for in life and at work? Starting with the end in mind goes far beyond knowing what you love or desire. This question requires considering why and what outcome you want from your personal and professional investment of time and energy. To answer this question, you have to factor in the impact you will have on others, what you stand for, and how you want to show up daily.

  2. What does personal and professional success look like this year and over the next five years? We are bombarded with images of what success should be. Images such as vacationing at a luxurious resort, buying a dream house, or driving a new car are images likely floating around your mind when you think about success. Also, our answers to this question are influenced by our culture and upbringing. When thinking about the answer to this question, consider the following types of success: material, emotional, intellectual, spiritual, physical, commercial, organizational, environmental, time, and team.

You can get the most out of these questions by taking these steps.

  1. Schedule some time in your calendar to reflect for ten minutes on each question. Discovering your answers can be challenging in a world full of suggestions for what success and significance should be.

  2. Ask yourself each question and journal what comes to mind. Don't filter. Just write it down. Journaling is often an underutilized tool. It is simply not enough to reflect. To gain traction, you need to be able to come back at a later time and reflect on your answers. If you aren't in the habit of journaling, you may like the structure and ease of the Day One app.

  3. Find a few people that know you well, that you trust, and will be encouraging of your exploration. Ask them how they would answer the questions for you.

  4. Consider hiring an executive coach. Some leaders become anxious with introspection. An effective executive coach will challenge assumptions and views and encourage, stretch, and challenge you. Coaching is a thought-provoking and creative process that inspires clients to maximize their personal and professional potential. Finding an individual leadership purpose can be challenging in a world full of powerful and influential advice about what success and significance look like.

  5. Reflect on what you heard. Consider themes rather than specific points shared and, as needed, edit or delete points you journaled.

Conclusion: Leadership bad habits don't have to be your destiny

Self-understanding is essential to breaking leadership bad habits. The bad habits of leadership that we have all witnessed or engaged in are not destiny. Striving for better habits is a competitive advantage available to any leader looking for a powerful point of differentiation.

Through a better understanding of personality traits, virtues, experiences, and purpose, you can get in front of the busyness of life as a leader and better persevere when life throws you a curveball.

What accidental leadership habit do you want to avoid, and what is your real challenge?


American Psychological Association. (n.d.). APA Dictionary of Psychology. American Psychological Association. Retrieved January 17, 2022, from

Daniels, A., & Daniels, J. (2006). Performance management: Changing behavior that drives organizational effectiveness. Performance Management Publications.

Egan, V., & Parmar, R. (2013). Dirty habits? online pornography use, personality, obsessionality, and compulsivity. Journal of Sex & Marital Therapy, 39(5), 394-409.

Judge, T., & Zapata, C. (2015). The person-situation debate revisited: Effect of situation strength and trait activation on the validity of the big five personality traits in predicting job performance. Academy of Management Journal, 58(4), 1149-1179.

Langford, P., Dougall, C., & Parkes, L. (2017). Measuring leader behaviour: Evidence for a "big five" model of leadership. Leadership & Organization Development Journal, 38(1), 126-144.

McCrae, R., & John, O. (1992). An introduction to the five-factor model and its applications. Journal of Personality, 60(2), 175-215.


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I hope you enjoy reading this blog post.

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Hi, I'm Dr. Jeff Doolittle. I'm determined to make your personal and professional goals a reality. My only question is, are you?

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About Dr. Jeff Doolittle

He is the founder of Organizational Talent Consulting in Grand Rapids, MI, and Program Director of online graduate and continuing business education at Olivet Nazarene University in Bourbonnais, IL. Executive leaders who work with Jeff describe him as thoughtful, decisive, intelligent, and collaborative. Jeff is a business executive with over twenty years of talent development and organizational strategy experience working with C-suite leaders in Fortune 100, Forbes top 25 private, for-profit, non-profit, and global companies in many industries.

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