164 Obstacles to Leadership and Business Success

Dive into the 164 ways leaders unknowingly block their own path to success, rooted in the psychological battleground of leadership. This blog not only identifies common pitfalls but also offers a guide for personal growth and transformative leadership, inviting you to turn obstacles into stepping stones for you and your team.

In the vast landscape of leadership, the journey to excellence is often marked by a series of hurdles—many of which are self-imposed. Through my extensive experience as an Executive Coach, working with a diverse group of companies and leaders, I've gathered insights into the common patterns that can trip up even the most promising leaders and teams. What emerges is a litany of challenges - both overt and subtle - that illustrates just some of the internal roadblock’s leaders face.

As Tony Robbins aptly puts it, success is 80% psychology and 20% skill. This emphasizes the profound impact of our mental frameworks and belief systems on our ability to lead effectively and build robust businesses. The following list of 164 potential stumbling blocks is comprised of issues I’ve seen first-hand that get in the way of leaders and their ultimate objectives. With awareness and practice, leaders can overcome these pitfalls and regain control over their goals and visions. Buckle up and let's unpack these challenges and discover strategies to navigate beyond them.

Consider if any of these points resonate with you and your experience. Addressing even just one could unlock your leadership potential, paving the way for higher achievement and success for both you and your team. 

164 Way Leaders Get in Their Own Way:

(in no particular order)

  1. Being Too Reliant on Others – The over-dependence on team members or partners, which can risk the leader's autonomy and decision-making capability.
  2. Not Celebrating Successes - Recognizing and appreciating achievements is crucial for morale and motivation within the team.
  3. The Perfectionist - Sets unattainably high standards, which can demoralize the team and slow progress due to fear of failure.
  4. Lack of Accountability - Leaders must own their mistakes and learn from them to foster a culture of responsibility and growth.
  5. Over-reliance on Traditional Methods - Sticking to the status quo without considering innovative approaches can stifle growth and adaptability.
  6. Failing to Adapt - Leaders need to stay flexible and responsive to new information to navigate the rapidly changing business landscape effectively.
  7. Not Prioritizing High Leverage Tasks - Focusing on tasks that offer significant returns or progress is essential for effective leadership and organizational success.
  8. Poor Time Management - Effective prioritization and time management are key to maximizing impact and achieving goals.
  9. The Micromanager - Focuses excessively on minor details, undermining trust and stifling team autonomy and creativity.
  10. Not Being Present - Fully engaging in the moment with team members and tasks is crucial for effective leadership and relationship building.
  11. Avoiding Risk - Embracing calculated risks is necessary for innovation and growth, as it opens up new opportunities and learning experiences.
  12. Not Setting Compelling Long-term Goals - Visionary objectives inspire and motivate teams, guiding them toward a shared future success.
  13. Failing to Encourage Creativity - Cultivating an environment where innovation thrives is essential for staying competitive and fostering team engagement.
  14. Overthinking or Over Intellectualizing - Decision-making can be hindered by excessive deliberation, leading to missed opportunities and stagnation.
  15. Not Practicing Leadership Daily - Consistent demonstration of leadership qualities is key to maintaining credibility and effectiveness.
  16. Failing to Invest in Leadership Development - Leadership skills require intentional development through training and mentorship for both oneself and the team.
  17. Ignoring One’s Physical Health - A leader's physical well-being significantly contributes to their effectiveness and endurance.
  18. Not Prioritizing Culture - The impact of culture on success and team morale cannot be overlooked; it's the foundation of a thriving workplace.
  19. Not Seeking the Counsel of a Trusted Advisor, Mentor, or Coach - External wisdom and perspective are invaluable for personal growth and overcoming challenges.
  20. Failing to Address Team Morale Proactively - Actively working to maintain and improve team morale prevents issues from significantly impacting performance.
  21. The People Pleaser - Strives to keep everyone happy, often at the expense of making tough but necessary decisions, which can lead to a lack of respect and loss of leadership authority.
  22. Not Encouraging Open Communication - A culture where all voices are heard fosters innovation, trust, and a sense of belonging among team members.
  23. Over-Reliance on Authority - Inspiring leadership, rather than leading through intimidation, encourages engagement and empowerment.
  24. Failing to Recognize External Pressures - Acknowledging and addressing the pressures employees face outside of work can significantly impact their performance and well-being.
  25. Poor Listening Skills - Truly understanding others is foundational to effective leadership, fostering trust and collaboration.
  26. Not Maintaining or Developing a Network - A robust professional network is crucial for growth, support, and opportunities.
  27. Avoiding Conflict - Addressing disagreements healthily can lead to growth, innovation, and stronger relationships.
  28. Failing to Delegate - Sharing responsibilities empowers others, builds trust, and enhances team capability.
  29. Overestimating the competition - Recognizing and leveraging the talents within oneself and the organization can lead to underestimated opportunities for growth and success.
  30. Not Fully Understanding Company Finances - A deep understanding of financial aspects is critical to the company's success and strategic decision-making.
  31. Failing to Experiment - Trying new approaches or solutions is essential for breakthroughs and continuous improvement.
  32. Ignoring Junior Team Members - Investing in the development of emerging talents ensures the organization's future leadership and innovation capacity.
  33. Misaligning Team and Organizational Goals - Ensuring team objectives support the broader mission is crucial for cohesive and strategic progress.
  34. Neglecting Diversity and Inclusion - Valuing diverse perspectives and backgrounds enriches the workplace and drives better decision-making.
  35. Failing to Encourage Self-Management - Empowering employees to set their own goals and manage their workloads increases engagement and accountability.
  36. Playing Favorites - Maintaining fairness and impartiality is crucial for trust and morale within the team.
  37. Overcomplicating Solutions - Simplicity and clarity in problem-solving enhance understanding and implementation.
  38. Not Aligning Actions with     Values - Decisions and actions should consistently reflect the organization's core values to foster trust and integrity.
  39. Ineffective meetings - Meetings should have a clear purpose and agenda to avoid wasting valuable time and to enhance productivity.
  40. Failing to Coach Your Team  Members - Providing consistent coaching supports individual growth and development, creating a pipeline of future leaders.
  41. The Scapegoater - Blames others for failures or issues, eroding trust and accountability within the team.
  42. Ignoring Company-Wide Mental     Health - Resources and support for mental health in the workplace are     essential for employee well-being and performance.
  43. Not Celebrating Individual Contributions - Acknowledging each team member's unique contributions fosters a sense of value and belonging.
  44. Over-reliance on Past Successes - Openness to new strategies and ideas is essential for adaptation and continued success.
  45. Failing to Cultivate a Sense of Belonging - Creating an environment where everyone feels valued and part of the team is key to engagement and retention.
  46. Overworking - Setting a sustainable pace is     crucial for long-term effectiveness and well-being for both leaders and their teams.
  47. Not Championing Employee Initiatives - Supporting and advocating for team members' projects and ideas encourages innovation and ownership.
  48. Failing to Recognize Team Dynamics - Understanding and nurturing interpersonal relationships, team chemistry, and morale are essential for a cohesive and productive team.
  49. A Need to Control - Exerting too much control can stifle autonomy, innovation, and team empowerment.
  50. Not Prioritizing Customer Feedback - Listening to and acting on customer feedback is crucial for meeting needs and driving improvements.
  51. Confusing Management for Leadership - Distinguishing between managing tasks and leading people is essential for empowering teams and fostering innovation.
  52. Abdicating Authority - Leaders must not shy away from making decisions or asserting their role to maintain credibility and direction.
  53. Ignoring the Power of Storytelling - Using narrative to inspire, connect, and communicate vision and values can profoundly impact engagement and understanding.
  54. Neglecting Cross-Functional Collaboration - Opportunities for departments to work together can lead to innovation and break down silos.
  55. Forgetting to Lead by Example - Modeling the behavior and values expected of others is foundational to credible and inspiring  leadership.
  56. Ignoring Work-Life Balance - Promoting a healthy balance is essential for sustainability and well-being.
  57. The Autocrat - Makes decisions unilaterally, limiting team engagement and innovation by not considering diverse viewpoints or fostering a collaborative environment.
  58. Inability to Show Vulnerability - Sharing personal challenges or weaknesses can humanize leaders and foster deeper connections and trust.
  59. Indecisiveness - Making timely and informed decisions is crucial for momentum and clarity.
  60. eI know better - Assuming one's approach is superior without considering others' input can limit perspectives and innovation.
  61. Isolated Too Much - Engaging with the relevant business community is essential for networking, growth, and staying informed.
  62. Lack of Agreements - Establishing clear expectations and commitments prevents misunderstandings and aligns efforts.
  63. Lack of Clarity in Vision - Articulating a clear and compelling vision guides and motivates the team towards shared goals.
  64. The Teflon Leader - Avoids taking responsibility for mistakes, letting issues slide off without addressing them, which can undermine credibility and accountability.
  65. Lack of Defined Company Purpose - Beyond revenue, a deeper mission and values drive engagement and give meaning to work.
  66. Lack of Empathy - Understanding and sharing the feelings of others is key to effective leadership and building strong relationships.
  67. Lack of Flexibility in Leadership Style - Adapting one's approach to meet diverse needs enhances effectiveness and team dynamics.
  68. Lack of Gratitude - Regularly expressing appreciation builds a positive team culture and reinforces valued behaviors.
  69. Lack of Self-Awareness - Reflecting on personal impact and areas for growth is essential for continuous improvement and effective leadership.
  70. Lack of Strategic Networking - Building and maintaining strategic relationships benefits the organization and personal growth.
  71. Lack of Transparency - Openness and honesty foster trust and open communication within the team and organization.
  72. Lack of Vision - A clear and compelling direction is necessary for guiding and inspiring the team towards future success.
  73. Learning from Failures - Viewing setbacks as growth opportunities fosters resilience and a culture of innovation.
  74. Misunderstanding Motivation - Recognizing the difference between intrinsic and extrinsic motivators can enhance motivation strategies.
  75. Neglecting Self-Development - Continuous personal growth is key to leadership effectiveness and adapting to new challenges.
  76. Neglecting Soft Skill Development - Communication, leadership, and teamwork skills are as important as technical skills for overall success.
  77. Not Addressing Burnout Proactively - Taking preventative measures against burnout protects well-being and maintains productivity.
  78. Fear of Change - Embracing change as an opportunity for growth is essential for innovation and staying competitive.
  79. Building Emotional Intelligence - High emotional intelligence is crucial for understanding and managing one's own emotions and influencing others.
  80. Creating an Environment of     Trust and Psychological Safety - A safe environment encourages risk-taking, voice, and innovation.
  81. Development of Emotional Intelligence - The ability to recognize and influence the emotions of others is a key leadership skill.
  82. Difficult Conversations - Addressing issues directly and constructively is necessary for resolution and growth.
  83. Ego-driven Decisions - Prioritizing the team's needs over personal ego ensures decisions are made for the right reasons.
  84. Ensuring the Development of Your Team - Investing in team members' growth contributes to organizational success and employee satisfaction.
  85. Ignoring One's Mental Health - Leaders must not neglect their well-being, as it's crucial for sustained effectiveness.
  86. Ignoring Succession Planning - Preparing for leadership transitions ensures organizational stability and continuity.
  87. Inconsistency - Consistent and predictable leadership provides stability and clarity for the team.
  88. Not Leveraging Employee Feedback - Acting on team insights can lead to meaningful improvements and increased engagement.
  89. Not Embodying the Organization's Purpose Daily - Living out the mission in daily actions reinforces values and guides behavior.
  90. Fear of Feedback - Viewing feedback as a gift allows for continuous improvement and personal growth.
  91. Scarcity Mindset - Operating from a mindset of abundance opens up possibilities and fosters a positive outlook.
  92. Shiny Object Syndrome - Focusing on strategic priorities rather than constantly chasing new trends ensures sustained progress.
  93. Shying Away from Difficult Things - Facing challenges head-on fosters growth, resilience, and problem-solving skills.
  94. Toxic Positivity - Acknowledging and addressing genuine concerns fosters authenticity and supports emotional well-being.
  95. Trying to Attract or Detract  from Attention - Managing visibility and influence effectively is key to leadership presence and impact.
  96. Underestimating Personal Impact - Recognizing the influence of one's leadership style is crucial for team morale and productivity.
  97. Underestimating the Competition - Staying informed about industry trends and competitors ensures strategic positioning.
  98. Underestimating the Value of Rest - Recognizing downtime's importance for creativity and productivity is essential for     sustainable success.
  99. Under communicating Expectations - Clear goals and standards guide team efforts and align with organizational objectives.
  100. Underutilizing Talents and Skills - Leveraging the diverse talents within the team enhances innovation and effectiveness.
  101. Too Isolated - Active engagement with the business community enriches leadership with new insights and opportunities.
  102. Anger Management - Controlling temper in stressful situations is crucial for maintaining professional relationships and credibility.
  103. Being Afraid to Hire - Expanding the team through delegation enhances capacity and allows for leadership focus on strategic     areas.
  104. Catastrophizing - Focusing on solutions rather than worst-case scenarios reduces stress and promotes proactive problem-solving.
  105. Disconnecting When Away - Truly disconnecting and recharging is vital for preventing burnout and maintaining productivity.
  106. Downplaying Abilities and Accomplishments - Recognizing and owning one's achievements builds confidence and leadership presence.
  107. Expecting Results Too Soon - Patience and persistence in strategy execution allow for meaningful and sustainable success.
  108. Fail Fail, Fail - Embracing failure as a learning opportunity encourages innovation and risk-taking.
  109. The Bystander - Avoids making decisions or taking a stance, leading to a lack of direction and uncertainty within the team.
  110. Flying Solo - Collaboration and support enrich leadership with diverse perspectives and shared expertise.
  111. Giving Away the Farm - Ensuring adequate compensation and setting boundaries prevent undervaluation and burnout.
  112. Hoarding All the Praise - Sharing success and recognition with the team fosters motivation and a sense of collective achievement.
  113. Jumping Ship Too Soon - Commitment to strategies or projects allows for their potential success and learning from the process.
  114. Just Doing Busy Work - Focusing on impactful tasks rather than busywork drives progress and strategic advancement.
  115. Keeping Up with the Joneses - Focusing on one's unique path and strengths rather than comparing to others supports authentic growth and satisfaction.
  116. Lack of Boundaries - Setting healthy limits with work, clients, or team members protects well-being and ensures focused effort.
  117. Lack of Self-Control - Managing impulses is key to thoughtful decision-making and leadership integrity.
  118. Loving One’s Product or Service Too Much - Openness to feedback and adaptation ensures products or services meet market needs and evolve.
  119. Manipulating Others - Ethical leadership and integrity in interactions build trust and long-term relationships.
  120. Never Asking for Help - Seeking assistance or advice when needed supports problem-solving and demonstrates humility.
  121. Not Thinking Big Enough - Visionary thinking inspires innovation and drives the team towards ambitious goals.
  122. Playing Well in the Sandbox - Effective collaboration with peers, partners, or competitors enhances outcomes and relationships.
  123. Setting Unattainable Goals - Realistic and challenging goals motivate and guide the team towards achievable successes.
  124. Trying to Do Too Many Things - Focused effort on strategic priorities enhances impact and prevents dilution of efforts.
  125. Working with Family or Friends - Navigating personal relationships in business requires clear boundaries and professional integrity.
  126. Always Focusing on What’s Wrong - Balancing awareness of challenges with recognition of successes fosters a positive and resilient team culture.
  127. An Autocratic Leader - Inclusive decision-making and empowering leadership styles foster creativity and team engagement.
  128. Confirmation Bias - Seeking diverse perspectives and challenging assumptions enhance decision-making and innovation.
  129. Fear of Firing - Making necessary personnel changes supports team performance and alignment with organizational standards.
  130. Fear of Investing in the Company - Allocating resources towards growth opportunities drives innovation and expansion.
  131. Inauthenticity - Genuine interactions and decisions build trust and strengthen team connections.
  132. Lack of Integrity - Upholding ethical standards is foundational to leadership credibility and organizational trust.
  133. Needing to Be the Smartest Person in the Room - Valuing collective wisdom over personal ego enriches leadership and decision-making.
  134. Needing to Belong - Making tough leadership decisions without seeking approval supports authenticity and effectiveness.
  135. Over reliance on Authority - Inspiring rather than intimidating leadership encourages team empowerment and innovation.
  136. Profits Over People - Prioritizing employee well-being and satisfaction drives engagement and long-term success.
  137. The Silent Judge - Critiques without offering constructive feedback, leaving team members confused about how to improve.
  138. Protecting Your People Too Much - Exposing the team to challenges fosters growth, resilience, and problem-solving skills.
  139. Relentless Drive - Balancing ambition with well-being prevents burnout and maintains team engagement.
  140. Selfish Leader - Putting the team's and organization's needs ahead of personal gains fosters trust and collective success.
  141. The Charmer - Relies on charisma rather than concrete action or competence, which can lead to a lack of substance and     unfulfilled promises.
  142. Too Conservative - Openness to risk and innovation ensures the organization remains competitive and adaptable.
  143. Too Critical - Balanced feedback supports growth and development while maintaining motivation and self-esteem.
  144. Too Distant and Inaccessible - Being available and approachable supports effective communication and team support.
  145. Tolerating Too Much - Addressing poor performance or negative behaviors maintains standards and team morale.
  146. Avoiding Setting Goals - Clear objectives provide direction and focus for the team, aligning efforts with organizational vision.
  147. Drugs and Alcohol - Addressing substance use issues is crucial for maintaining decision-making quality, leadership, and overall performance.
  148. Making Excuses - Taking responsibility for actions and decisions enhances leadership credibility and fosters a culture of accountability.
  149. Mental Illness - Addressing mental health issues supports personal well-being and sustained leadership effectiveness.
  150. Needing to Be “Right” - Embracing collaborative progress and learning from mistakes fosters innovation and team development.
  151. I want to Belong - Balancing the need for approval with leadership responsibilities ensures decisions are made in the organization's best interest.
  152. Diverse Perspectives Outside The Organization - Seeking insights beyond the internal environment enriches strategy and innovation.
  153. The Quick Fix - Addressing underlying issues rather than opting for temporary solutions prevents recurring problems and fosters sustainable improvements.
  154. Too Many Cooks in the Kitchen - Clarifying decision-making processes and roles ensures efficiency and prevents confusion.
  155. Staying in a Toxic Environment - Seeking change or exiting negative situations protects well-being and fosters a positive work environment.
  156. Resistance to Technology - Embracing technology enhances efficiency, innovation, and competitiveness.
  157. Poor Communication - Clarity, consistency, and effectiveness in messaging ensure alignment and understanding across the team.
  158. People Pleasing - Balancing the desire to satisfy with leadership effectiveness prevents compromise on vision and standards.
  159. Promoting A Team Dynamic - Building collaborative teams that work together enhances outcomes and fosters a supportive culture.
  160. Overemphasis on Short-term Goals - Balancing short-term wins with long-term vision ensures sustained progress and strategic alignment.
  161. Overlooking Continuous Learning - Fostering a culture of personal and professional development supports adaptability and innovation.
  162. Prioritizing Oneself - Balancing personal needs with those of the team and organization ensures leadership effectiveness and     team harmony.
  163. The Visionary Without Detail - Inspires with big ideas but often overlooks the practical steps needed for implementation, leading to     confusion and unmet goals.
  164. Avoiding the Spotlight - Shying away from the spotlight will diminish the opportunities ahead and weaken your leadership.


First off, kudos to you if you’re still reading! That’s a long list. Now that you’re this far, consider which points hit close to home. Acknowledging these isn't a sign of weakness, but rather a powerful step towards growth. Your leadership journey is unique, filled with specific challenges that, when overcome, not only enhance your capabilities but also uplift your entire team and will lead to your success!

Craft a personal roadmap for tackling these challenges. Support from a mentor, executive coach, and a peer can be a game changer in this journey. Remember, overcoming these obstacles not only marks your growth but also benefits everyone around you. May we all strive for a leader that elevates everyone around us. Here's to navigating through our challenges and celebrating the collective wins ahead.