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Key Takeaways
- Being fired, especially more than once, can shake your confidence. Make sure you center yourself, assess your skills and market yourself accurately in future job interviews.
- You cannot anticipate every difficult board, cultural mismatch or biased leader. That said, you can still focus on building your self-awareness, investing in your growth and carefully evaluating your next opportunity so you stop repeating the same cycle.
As a tech career and executive coach, one of the most frustrating issues I see senior leaders face is having an impressive track record, yet being let go more than once and not being able to figure out why. When you’re terminated at the leadership level, feedback is often minimal or non-existent, leaving you wondering what happened and what you can do differently next time.
Here’s an important distinction: Being fired isn’t the same as being laid off. Layoffs are ravaging the tech industry. This article isn’t about them. It’s specifically for leaders who have been let go for performance, behavior, or fit-related reasons and who keep finding themselves in the same situation.
When you get fired, especially more than once, it’s worth looking inward. The goal isn’t to assign blame but to identify what’s within your control and can be changed and what isn’t.
1. Did you adequately vet the company before joining?
Most leaders prepare obsessively for interviews but rarely invest equal time evaluating whether a potential company, culture, board or role is truly right for them. Interview processes are designed to sell you on the company, which means you must actively push back to ensure the fit works both ways. This is particularly important at the leadership level, where value mismatches can quickly lead to termination.
Reflecting back, did you talk to people who left before accepting the role? Did you ask why the last person in this role left and how long they lasted? Did you understand the board’s priorities and what success would look like at 90 days, six months and one year?
Spend ample time on due diligence before accepting your next offer. Go beyond Glassdoor. Use LinkedIn to find former employees and request honest conversations about their experience. You must be prepared to define your non-negotiables before an offer is in front of you, not after.
2. How big is the gap between who you said you were in the interview and the person who showed up when things got hard?
This question has two distinct layers. The first is how you represented yourself coming in. Sometimes, overselling is deliberate. Other times, it’s a genuine mismatch between your confidence and your actual readiness. The second layer is the way you held up under pressure.
I coached a leader who described herself as being levelheaded in interviews but then going silent during a brutal product launch. Her team felt abandoned. I coached another leader who prided himself on being direct but then learned through a 360 that his directness was perceived as aggressiveness. In both cases, the gap between who they said they were and who showed up under stress was what ultimately cost them their roles.
3. Are you navigating organizational politics, or are you avoiding them?
Many leaders push back on the word “politics,” so here’s a simple reframe: At the executive level, there are no politics. There’s only relationship-building, and it’s a core part of your job.
At the individual contributor level, great work often speaks for itself. At the leadership level, it rarely does. I’ve worked with fabulous leaders who alienated their cross-functional peers by treating every meeting as a problem to solve rather than a relationship to build. They were often the first to be cut when a reorg came.
Map your informal network before your next role starts and then identify the gaps. Invest in relationships before you need them. Pay attention to what is left unsaid in meetings, as the conversation after the meeting is often the real one. Find someone who will share some of that feedback with you.
4. Could discrimination be playing a role?
Not every firing reflects something you could or should have changed. Discrimination is real, and it is far too often disguised as “culture fit” or “executive presence.”
As I’ve written previously, executive presence is rooted in outdated notions of professionalism that frequently put LGBTQ+, BIPOC and other historically marginalized leaders at a disadvantage simply for being themselves. I’ve worked with leaders who received consistent feedback about executive presence while their straight, white, male peers with weaker results were described as high-potential.
If you believe discrimination played a role in your termination, document everything and consider consulting an employment attorney. You don’t need to know for certain whether it was discrimination ahead of time. That’s what lawyers are for.
5. Are you surrounding yourself with people who will tell you the truth?
The higher you climb, the fewer people will tell you what you actually need to hear. It’s not that people become dishonest, it’s just that the risk of telling a senior leader something difficult goes up considerably as you advance.
Unfortunately, many leaders don’t invest in coaching until after their second or third termination. The question isn’t whether they needed the support but why they waited so long. In most situations, the reason they got fired is that no one told them the truth.
Try conducting an informal 360-degree evaluation by talking to people who know your work and will be direct. Ask specific questions like, “How do I show up under pressure?” and “What do people say about me when I’m not in the room?” You can also use a formal assessment like the EQ 360, which allows you to gather anonymous, structured feedback through an executive coach who will ask the questions others refuse to.
Final thoughts
Being fired, especially more than once, can shake your confidence. Before your next job search, sit with these questions:
- Did you vet the company as carefully as they vetted you?
- How big is the gap between who you said you were and the way you showed up when things got hard?
- Are you navigating organizational politics, or are you avoiding them?
- Could discrimination be playing a role that deserves to be named and taken seriously?
- Are you surrounding yourself with people who will tell you the truth?
You cannot anticipate every difficult board, cultural mismatch or biased leader. That said, you can still focus on building your self-awareness, investing in your growth and carefully evaluating your next opportunity so you stop repeating the same cycle. You’ve got this!
Key Takeaways
- Being fired, especially more than once, can shake your confidence. Make sure you center yourself, assess your skills and market yourself accurately in future job interviews.
- You cannot anticipate every difficult board, cultural mismatch or biased leader. That said, you can still focus on building your self-awareness, investing in your growth and carefully evaluating your next opportunity so you stop repeating the same cycle.
As a tech career and executive coach, one of the most frustrating issues I see senior leaders face is having an impressive track record, yet being let go more than once and not being able to figure out why. When you’re terminated at the leadership level, feedback is often minimal or non-existent, leaving you wondering what happened and what you can do differently next time.
Here’s an important distinction: Being fired isn’t the same as being laid off. Layoffs are ravaging the tech industry. This article isn’t about them. It’s specifically for leaders who have been let go for performance, behavior, or fit-related reasons and who keep finding themselves in the same situation.
When you get fired, especially more than once, it’s worth looking inward. The goal isn’t to assign blame but to identify what’s within your control and can be changed and what isn’t.
