Why good professionals derail: Common pitfalls on the leadership track

Climbing the leadership ladder is both a professional aspiration and a potential trap. While technical expertise, ambition, and a solid track record may open leadership opportunities, sustaining success in such roles demands an entirely different skill set. Many professionals falter in predictable ways—missteps that can not only derail their careers but also damage the culture and performance of their organisations.

One of the most common pitfalls is the failure to transition from individual contributor to true leader. New managers often continue to execute tasks themselves rather than empowering their teams. According to Harvard Business School's Leadership Gaps report, this tendency to micromanage limits scalability, erodes trust, and stunts team development. High-performing teams thrive on autonomy—not constant oversight.

This challenge aligns with the Peter Principle, a well-known management theory suggesting that individuals are promoted until they reach a level beyond their competence. For instance, a star engineer or sales executive might be promoted to a managerial position without the interpersonal or strategic leadership skills required—resulting in poor outcomes despite past successes.

Another frequent mistake is avoiding difficult conversations. As the Forbes Tech Council notes, leaders who shy away from honest feedback often foster confusion and disengagement. When issues aren’t addressed promptly, they tend to fester, leading to frustration, misalignment, and eventually, turnover. Constructive confrontation—when approached with empathy and clarity—strengthens trust and reinforces accountability.

Equally damaging is poor listening. According to the Fellow Blog, “not listening to your team” ranks among the top 10 leadership failures. Leaders who dominate conversations or dismiss input risk losing valuable insights and weakening morale. Practising active listening—asking clarifying questions, acknowledging feedback, and demonstrating appreciation—can significantly improve cohesion and decision-making.

This challenge is widespread. As highlighted in Forbes’ The Listening Crisis, nearly 70% of employees feel their feedback is ignored, particularly during periods of organisational change. Overlooking employee voices not only leads to disengagement but also increases resistance to transformation. Leaders who fail to listen send a clear signal: that employee input doesn’t matter.

Closely tied to this is a lack of self-awareness. Leaders who fail to reflect on their behaviour, motivations, and impact often operate with significant blind spots. This becomes even more problematic when coupled with ego-driven leadership or overconfidence. Ironically, feedback aversion is most common among senior leaders—those who most need it. As Forbes highlights, self-awareness is a key predictor of leadership effectiveness. Leaders who understand their emotional triggers, biases, and interpersonal tendencies are far better equipped to adapt and inspire.

Another silent but serious trap is neglecting personal growth. Leadership is not a destination but an evolving discipline. Many leaders focus so intently on results that they overlook essential soft skills like empathy, adaptability, and collaboration. Harvard Business School underscores that it’s often the absence of these interpersonal skills—not technical knowledge—that leads to leadership derailment.

A compelling case study of successful leadership transformation is Tufan Erginbilgiç, CEO of Rolls‑Royce since January 2023. When he took over, the company was struggling with financial distress and structural inefficiencies. Erginbilgiç acted decisively: streamlining operations, flattening the hierarchy, and articulating a clear, focused vision. His transparent communication and bold reforms helped restore confidence among employees and investors alike. Within a year, Rolls‑Royce more than doubled its profits and saw a share price surge of over 60%. His disciplined approach and cultural reset proved essential in turning a legacy manufacturer into a revitalised leader.

By contrast, the downfall of Adam Neumann, former CEO of WeWork, illustrates how unchecked ambition and poor self-regulation can undermine leadership. Neumann’s refusal to heed feedback from stakeholders and his insular decision-making led to a dramatic collapse in company valuation and his eventual exit. His story serves as a cautionary tale: when leaders ignore dissent and resist accountability, the consequences can be swift and severe.

Can leaders proactively avoid these pitfalls?

Yes, and others have done it, although they often had to hit a low in order to learn the lesson. Here are some strategies that help.

Shift from control to coaching. Build systems that allow others to shine. Empower your team rather than micromanaging them.

Create consistent feedback loops. Use regular one-on-ones, surveys, and anonymous channels to encourage upward feedback.

Model psychological safety. Invite dissenting views, reward candour, and address issues early and openly.

Invest in self-awareness. Use tools like 360° feedback, coaching, and personality assessments to better understand how others perceive your leadership.

Prioritise continuous learning. Make time for reading, reflection, and development—not just performance metrics.

Protect your energy. Set boundaries and model work-life balance to prevent burnout and support long-term sustainability for yourself and your team.