Understanding Why You Keep Getting Fired from Leadership Roles
Being fired, particularly more than once, can profoundly shake your confidence and leave you questioning your professional value. For senior leaders with impressive track records, repeated terminations can be baffling, especially when feedback from employers is minimal or absent. As a tech career and executive coach, I’ve seen many leaders struggle with this perplexing pattern. It’s important to recognize that being fired for performance, behavior, or cultural fit is distinct from being laid off. While layoffs have become widespread in the tech industry, this discussion focuses on leaders who face termination due to reasons tied to their leadership style or organizational fit.
When confronted with repeated firings, the key is introspection—not blame. Understanding what factors are within your control and which are not can help break the cycle and guide your future career decisions.
1. Did You Adequately Vet the Company Before Joining?
Leaders often prepare exhaustively for interviews but rarely dedicate equal effort to evaluating whether a company’s culture, board, and role align with their values and working style. Interview processes are designed to sell the company to candidates, so it is crucial to push back and ensure the fit works both ways—especially at the leadership level where mismatches in values or expectations can lead to early termination. According to Entrepreneur, value mismatches are a common cause of leadership turnover.
Before accepting a leadership role, ask yourself: Did I speak with former employees or leaders who previously held this position? Did I inquire why the previous occupant left and how long they lasted? Did I understand the board’s priorities and what success would look like at key milestones such as 90 days, six months, and one year?
Due diligence is essential. Go beyond public reviews on platforms like Glassdoor by leveraging LinkedIn to connect with former employees for candid discussions. Defining your non-negotiables before an offer is on the table can prevent costly missteps.
2. How Big Is the Gap Between Who You Said You Were in the Interview and Who Showed Up When Things Got Hard?
This question has two important layers. First, consider how you presented yourself during the interview process. Sometimes leaders oversell their capabilities intentionally, while other times there’s a genuine disconnect between confidence and readiness. Second, reflect on how you responded under pressure.
For example, a leader might describe herself as calm and composed during interviews but become withdrawn during a critical product launch, leaving her team feeling unsupported. Another might pride himself on being direct but later discover through 360 feedback that his style was perceived as aggressive. These discrepancies between projected image and actual behavior under stress often contribute to termination.
3. Are You Navigating Organizational Politics, or Are You Avoiding Them?
Many leaders bristle at the term “politics,” but at the executive level, what is often called politics is really about relationship-building. Unlike individual contributor roles where work can speak for itself, leadership positions demand active cultivation of networks and alliances.
Research shows that leaders who fail to build strong cross-functional relationships risk alienation and are more vulnerable during organizational changes such as restructurings. Mapping your informal network before starting a role and identifying gaps allows you to invest in relationships proactively. Pay close attention to what’s left unsaid in meetings—the informal conversations afterward often carry the real insight. Finding trusted colleagues who will provide candid feedback is invaluable.
4. Could Discrimination Be Playing a Role?
It’s critical to acknowledge that not every firing is due to something within your control. Discrimination remains a pervasive issue disguised as “culture fit” or “executive presence.” Studies and anecdotal evidence indicate that leaders from marginalized groups—such as LGBTQ+, BIPOC, and women—often face biased assessments rooted in outdated norms of professionalism.
For example, leaders who are authentic may receive negative feedback on their “executive presence” while less effective, majority-group peers are labeled as “high potential.” If you suspect discrimination contributed to your termination, documenting everything and consulting an employment attorney is a prudent step. You don’t have to prove discrimination on your own—that is what legal experts are for.
5. Are You Surrounding Yourself with People Who Will Tell You the Truth?
As you ascend the corporate ladder, honest feedback becomes scarcer. It’s not that people become dishonest but that the risk of delivering unwelcome truths to senior leaders increases significantly. Many executives only seek coaching after multiple terminations, but early and ongoing feedback is essential to leadership success.
Consider initiating an informal 360-degree evaluation by soliciting feedback from colleagues who know your work and can be candid. Ask pointed questions like, “How do I perform under pressure?” or “What do people say about me when I’m not present?” Formal assessments such as an EQ 360, administered through an executive coach, can provide structured, anonymous insights that others may be reluctant to share.
Final Thoughts
Repeated firings can erode confidence, but they also offer an opportunity for deep reflection and growth. Before embarking on your next job search, ask yourself:
- Did I vet the company as carefully as they vetted me?
- How big is the gap between who I said I was and how I showed up under pressure?
- Am I actively navigating organizational dynamics or avoiding them?
- Could discrimination be a factor that needs to be acknowledged and addressed?
- Am I surrounded by people who will tell me the hard truths I need to hear?
While you can’t predict every challenging board, cultural mismatch, or biased leader, focusing on self-awareness, continuous growth, and thorough evaluation of new opportunities can help you break the cycle and thrive in your leadership career. Remember, resilience and insight are your greatest assets moving forward—you’ve got this!
