Career Mistakes Executives Keep Making (And How to Fix Them Before They Cost You Big)

Executives are supposed to have it all figured out, right? Wrong. Even the best leaders make missteps, and sometimes costly ones. The difference between those who continue to rise and those who stall is simple: self-awareness and course correction.

If you’ve spent years climbing the corporate ladder, you know firsthand that career growth at the top isn’t just about strategy and execution. It’s about navigating relationships, staying adaptable, and ensuring your value is recognized (without working yourself into the ground).

Let’s talk about some of the biggest mistakes I see executives make and more importantly, how to fix them before they hold you back.

1. Staying Because It’s Comfortable

💡 Fix It: Always keep one foot in the market. Update your resume quarterly. Take recruiter calls. Interview when you don’t need to. Nothing will make you feel more “stuck” than realizing you should have left years ago.

2. Thinking Hard Work Speaks for Itself

💡 Fix It: You might be leading with results, but are you making sure they’re seen? Visibility matters. Ensure your wins are strategically shared, whether that’s through board meetings, internal reports, or even well-placed LinkedIn updates.

3. Becoming Too Essential

💡 Fix It: If your team (or company) can’t function without you, congratulations—you’ve built a trap. Great leaders create systems and train replacements so they can step into bigger roles, not get stuck firefighting daily operations.

4. Ignoring Office Politics (Or Thinking You’re Above It)

💡 Fix It: You don’t have to play dirty, but you do have to play smart. Relationships with key decision-makers above you matter. Build three allies at a higher level and check in with them regularly.

5. Thinking Your Network Will Always Be There

💡 Fix It: Your network is a living, breathing asset but only if you nurture it. Don’t just reach out when you need something. Schedule one strategic connection a month, offer value, and keep relationships warm.

6. Not Positioning Yourself for the Next Role

💡 Fix It: If you’re eyeing the C-suite (or a bigger opportunity), your brand needs to reflect it before you get there. Share thought leadership, mentor rising leaders, and make it clear you’re operating at the level you aspire to.

7. Avoiding Tough Conversations

💡 Fix It: High-level leadership isn’t about keeping the peace—it’s about strategic conflict resolution. Whether it’s pushing back on unrealistic expectations or addressing underperformance, executives who avoid hard conversations lose credibility fast.

8. Waiting for the “Right” Moment to Negotiate

💡 Fix It: The best time to negotiate isn’t at the offer stage—it’s before you ever need a new role. Know your market value, track your wins, and don’t wait until you’re desperate to start having those conversations.

9. Failing to Adapt to Industry Shifts

💡 Fix It: Just because you’ve “made it” doesn’t mean you can stop learning. The most respected executives are lifelong learners. Stay on top of market trends, emerging tech, and leadership strategies. Complacency is a career killer.

10. Not Thinking Like a Business Owner

💡 Fix It: Whether you’re leading a division or running the whole company, operate like an owner. Understand P&L, drive strategic growth, and think beyond your own role. Executives who act like CEOs (even before they have the title) are the ones who land the seat.

Final Thought

The higher you climb, the more intentional you have to be about your career moves. Don’t assume longevity equals security. Position yourself strategically, stay visible, and always be prepared for the next opportunity before you need it.

Which of these mistakes have you seen (or made)? Let’s talk in the comments.

🚀 Need a career strategy that actually works? Let’s chat. Book a consultation here.