The Biggest Career Derailer May Be Refusing to Admit You Need Help.
Updated: 23h
The Biggest Career Derailer May Be Refusing to Admit You Need Help.
Why accomplished executives sometimes become their own greatest obstacle to sustained success.
Over the course of my career, I've watched some exceptionally capable people undermine otherwise promising careers. Not because they lacked intelligence, experience, ambition, or a strong work ethic. In fact, many possessed those qualities in abundance.
Their problem was more difficult to recognize. They couldn't bring themselves to acknowledge that they needed help.
There's a certain irony here. The qualities that help someone rise through an organization - confidence, independence, decisiveness, and a willingness to take responsibility - can become liabilities if taken too far. Somewhere along the way, successful executives can begin to believe that asking for guidance, admitting uncertainty, or acknowledging a blind spot will diminish their credibility.
In my experience, the opposite is often the case.
I've seen executives defend poor decisions long after the evidence pointed to a different course. I've watched talented leaders dismiss feedback because it challenged their self-perception. And I've seen people resist coaching because they believed it was reserved for struggling executives.
The common denominator wasn't a lack of ability. It was an unwillingness to recognize that ability alone was insufficient.
Unfortunately, by the time some leaders recognize the problem, the damage to their effectiveness, reputation, or career may already be significant.
When Success Becomes a Liability
Early in our careers, most of us are comfortable admitting what we don't know. We ask questions, seek advice, and look for mentors to help us navigate unfamiliar situations. Then something changes. As we become more successful, people increasingly turn to us for answers. Our opinions carry greater weight, and our decisions affect more people, larger budgets, and increasingly important business outcomes.
Gradually, the expectation that we should have the answers can become a belief that we must have them.
Consider an executive known for making difficult decisions quickly. That decisiveness may have contributed significantly to their success. But as the organization grows and decisions become more complex, the same executive may start making judgments without adequately considering other perspectives.
What was once a strength can become a limitation.
Sometimes the behaviors that helped us succeed at one level are precisely the ones we need to reconsider to succeed at the next. Experience is a tremendous asset, but it can also make us overly confident in our judgment.
The Blind Spots We Don't Know We Have
One of the difficult realities of executive leadership is that we don't always see ourselves as others do. We judge ourselves largely by our intentions, while others judge us by our behavior and its impact.
An executive may believe they're encouraging healthy debate, while their team experiences their questions as criticism. Another may consider themselves highly accessible, while employees have learned that raising uncomfortable issues rarely ends well.
Neither leader necessarily intends to create these conditions. But intention doesn't eliminate impact.
Organizational psychologist Tasha Eurich has conducted extensive research on self-awareness. In a 2018 Harvard Business Review article, she reported that although 95% of people in her research believed they were self-aware, only about 10–15% met the researchers' criteria for self-awareness.
Those findings highlight a meaningful problem: our confidence in how well we understand ourselves may exceed reality.
The problem becomes more pronounced as leaders rise through an organization. People become increasingly selective about what they say to those who control budgets, promotions, compensation, and career opportunities.
The higher the position, the greater the likelihood that important information is filtered before it reaches the executive.
Leadership can become lonely. It should never become insulated.
Why Asking for Help Feels So Difficult
If executives recognize the value of feedback and development, why do some resist it? I believe several factors contribute.
There's the issue of identity. Successful executives have spent years building reputations for competence and sound judgment. Acknowledging they need help can feel like calling into question the qualities that define their success. There's also concern about perception. Some worry that seeking coaching or outside advice will signal uncertainty to colleagues or the board.
And there's the discomfort of vulnerability. Genuine development requires acknowledging that some of our behaviors may be contributing to the problems we're experiencing. Yet the reluctance to seek help often creates a greater risk than the perceived embarrassment of asking for it.
Asking for help doesn't automatically diminish credibility. Under the right circumstances, it can strengthen it. Of course, there's a difference between seeking thoughtful guidance and expecting others to make decisions for you. Accountability and independence are not the same thing.
The Cost of Waiting Too Long
One unfortunate pattern I've observed is that executives often become receptive to coaching only after a problem arises.
A disappointing performance review. A failed strategic initiative. Unexpected turnover among valued employees. A difficult conversation with the board. Being passed over for a promotion. Sometimes the warning signs have been present for years.
Colleagues may have tried to raise concerns. Employees may have offered subtle feedback. Business results may have indicated that a different approach was needed. But the executive either failed to recognize the signals or chose to explain them away. By the time the situation becomes impossible to ignore, the options may be considerably more limited.
This is why I believe executive coaching and independent advisory relationships are most valuable when treated as investments in sustained effectiveness rather than as interventions reserved for struggling leaders. A successful executive doesn't need to be in trouble to gain a different perspective. In fact, some of the greatest opportunities for development arise when things are going well. That's when leaders have the time, credibility, and organizational support to assess their effectiveness before a problem becomes a crisis.
It's also when they may be least inclined to do so.
The Value of Someone Who Will Challenge Your Thinking
Every executive needs people willing to tell them what they need to hear, not just what they want to hear. During my years as COO of Credico, I worked with hundreds of independent sales organizations and a leadership team responsible for everything from operations and finance to client relationships and compliance. It was a complex business, and there were many times when a decision that seemed perfectly reasonable from one perspective looked quite different when viewed from another.
One lesson that experience reinforced for me was the importance of having people around you who were comfortable challenging your thinking. I didn't need everyone to agree with me. I needed people who understood aspects of the business I might not see as clearly and who were willing to say so.
After decades in executive roles, I had plenty of experience to draw on. But experience doesn't give you a monopoly on good judgment. Sometimes it simply makes you more confident in an assumption that deserves to be questioned.
I've come to believe that one of the more important responsibilities of a senior executive is to create an environment where people can challenge your thinking without fear of consequences. That begins with how you respond when someone tells you something you'd rather not hear.
This is also where trusted advisors and executive coaches can make a meaningful impact. A business advisor with substantial operating experience can help an executive evaluate decisions, recognize patterns, and avoid mistakes others have already made. An executive coach provides a confidential environment where leaders can examine assumptions, identify behavioral patterns, and develop their own solutions.
Neither relationship replaces the executive's judgment, but both can improve it.
The challenge isn't simply finding people willing to offer advice. It's being genuinely willing to listen. Sometimes the most valuable conversation an executive can have is the one they'd rather not have.
What Effective Leaders Do Differently
I don't believe the best leaders necessarily have fewer blind spots than others. They're simply more willing to uncover them.
They understand that professional development doesn't end with a promotion, a prestigious title, or decades of experience.
They seek perspectives from people who view the organization differently. They invite challenges to their assumptions before making consequential decisions.
Importantly, they do something with what they learn. Feedback without reflection accomplishes little. Reflection without behavioral change accomplishes even less.
A leader who repeatedly asks for input but never adjusts their approach eventually teaches people that their feedback is ignored.
The true measure of openness isn't whether someone is willing to hear difficult information. It's whether they're prepared to act on it.
There's a meaningful difference between being confident in your abilities and believing you've outgrown the need for further development.
A Final Thought
After more than four decades in business, I'm convinced that few executives reach their full potential entirely on their own.
No matter how accomplished we've become, there will always be something we don't see, something we haven't considered, or a behavior that's limiting our effectiveness. The question isn't whether we have blind spots. We do. The question is whether we're willing to acknowledge them before they shape our careers in ways we never intended.
At Opus One Advisory, our executive coaching work helps accomplished leaders gain perspective, examine assumptions, confront blind spots, and strengthen their effectiveness. Not because they're failing, but because their continued success matters.
The biggest career risk may not be needing help. It may be becoming the last person to recognize that you do.
