Leadership Derailers. THE LEADERSHIP EDGE! Newsletter September 2025
THE LEADERSHIP EDGE
Your Guide to Exceptional Leadership
September 2025 | 1001 words = 4.25-minute read
1. Executive Coaching Works – depending on the study, the ROI to coaching is outstanding!
2. Selection – strength builder or fixer? Do they use an assessment? What’s their process?
3. Assess Your Motivation and Set a Goal – without high motivation to change, you will not change just because you have a coach
THIS MONTH’S FOCUS
Leadership Derailers You Can't See Coming
Hello Leaders! This month, it's all about the leadership derailers that could catch you off guard and negatively impact your leadership effectiveness. There are a lot of things that can prevent a good leader from becoming a great leader. I want to draw your attention to seven of the most insidious derailers. If this sparks an interest and you'd like to schedule a discussion, you can do so here.
Point #1: Blind Spots & Derailers
Leadership derailers are patterns of behavior that can undermine even talented leaders as they advance in their careers. The most challenging derailers are those that you never see – a blind spot. A blind spot is just that – blind. When I ask leaders, 'Are you a good leader?' most say, 'I think so... my team likes working for me and my boss likes what I'm doing, so I guess I'm doing pretty well." You can hear it in their tone; they are somewhat unsure whether they have something that needs to be addressed. They don’t know if there is something, but since no one has said anything, they are okay.
That’s a dangerous way to be a leader. The feedback that a leader needs to continue to improve constantly needs to have corrective information. Derailers are often so seemingly negative that they are the last thing that your team or your peers will bring to your attention. Even if your manager has a great relationship with you, they may take the risk to bring a derailer to your attention, but they often prefer to look the other way rather than upset you or make you worry that something is wrong. As a leader, depending on the 'nobody has said anything to me' factor doesn't mean you don't have a derailer – just because you can't see something doesn't mean it isn't there.
REFLECTION: Who can I ask who will give me a direct answer about any derailers / blind spots that I may have?
Point #2: The Big Seven
Here are seven of the most significant derailers that good leaders may encounter:
Arrogance and Loss of Self-Awareness. Success can breed overconfidence, leading leaders to stop seeking feedback, dismiss others' ideas, or believe they're infallible. They may become isolated from ground-level realities and make decisions based on outdated or incomplete information.
Micromanagement and Control Issues. As stakes increase, some leaders struggle to delegate effectively. They become bottlenecks, stifle their teams' growth, and burn themselves out trying to control every detail rather than empowering others.
Inability to Adapt Leadership Style. What works at one level may fail at another. Leaders who can't adjust their approach as they move from managing individuals to leading teams to running organizations often plateau or fail.
Emotional Volatility. Under pressure, some leaders lose emotional regulation. Outbursts, mood swings, or inability to handle stress gracefully can destroy trust and create toxic work environments, regardless of their technical competence.
Political Blindness. Talented individual contributors often struggle with organizational politics. They may be naive about power dynamics, fail to build necessary alliances, or alienate key stakeholders through poor political judgment.
Perfectionism and Decision Paralysis. The desire to make perfect decisions can paralyze leaders, especially as decisions become more complex and consequential. This often leads to missed opportunities and frustrated teams waiting for direction.
Failure to Develop Others. Leaders who focus solely on personal achievement may neglect the importance of mentoring and developing their teams. This creates succession problems and limits organizational growth while potentially breeding resentment.
REFLECTION: Which one of the seven do I have the greatest chance of falling prey to?
Point #3: It’s Not What You Know…
The insidious nature of these derailers is that they often emerge from strengths taken too far or from behaviors that previously drove success. Regular self-reflection, seeking feedback, and maintaining strong support networks are crucial for recognizing and addressing these patterns before they become career-limiting.
Most of the executives I work with as their leadership coach are good leaders, some are even great. And guess what? They still have opportunities to make a bigger difference and increase their influence. The challenge for many is that they are good, maybe excellent, at some aspects of the business. Over-indexing on that thing you know or are really good at often takes up most of your energy and focus. It limits your attention to your leadership effectiveness and may enable a blind spot.
I have a client who is the CEO of an international organization. He views the organization through his own actions, communications, and customer interactions. A good leader does just what I have described. But a great leader sees the organization and their personal impact through what their people are doing, how effective they are, and the successes and failures they experience.
Extraordinary leaders lead and get out of the way of their people. If an executive has a derailer, the great CEO lovingly points it out, expects the executive to develop a plan, and immediately put that plan into action. Great leaders would never let someone on their team languish with a derailer.
Be careful about having great technical ability. If you've reached the executive suite because of it, it may be the thing you need to assess how much it gets in the way of leading others. Experts often have a challenging time becoming an extraordinary leader. By the time you reach the C-suite, your leadership is more important than what you know or can do.
REFLECTION: Do I depend too much on my intelligence, expertise, or technical skill(s)?
Dive Deeper:
1. Derailed: Five Lessons Learned from Catastrophic Failures of Leadership by Tim Irwin
2. Why CEO's Fail: The 11 Behaviors That Can Derail Your Climb to the Top and How to Manage Them by David Dotlich and Peter Cairo
3. Leadership Lessons of the Navy SEALS: Battle-Tested Strategies for Creating Successful Organizations and Inspiring Extraordinary Results: ... and Inspiring Extraordinary Results by Jeff Cannon and Jon Cannon
The Leadership Edge - Sharpening your leadership skills, one insight at a time.