Critical Traps Even Experienced CEOs Shouldn’t Fall Into

Critical Traps Even Experienced CEOs Shouldn't Fall Into

Working with Boards and CEOs through transitions, I've learned something counterintuitive: Experienced CEOs sometimes struggle more than first-timers when taking on a new CEO mandate. Not because they're less capable, but because success in one CEO role sometimes creates dangerous blind spots in the next.

Experienced CEOs sometimes struggle more than first-timers when taking on a new CEO mandate.

If you're stepping into your second or third CEO position, you might be reading this thinking, "I've done this before. I know what I'm doing." That confidence is both your greatest asset and your biggest vulnerability.

And here's something you probably remember but might have forgotten the intensity of: The CEO role is profoundly lonely.

The CEO role is profoundly lonely.

More lonely than almost any other position. You discovered this the first time, and you might hope it's different now. It's not. If anything, the isolation intensifies - because people assume you have it figured out, so they offer even less support.

The Traps

Here are some traps we see repeatedly when CEOs take over new mandates - some universal, others specific to experienced leaders who should know better but sometimes fall into them anyway.

Trap 1: The "I've Done This Before" Trap

The trap: Your success in your last CEO role doesn't transfer as cleanly as you think.

Your playbook that worked brilliantly in your last mandate might create resistance and confusion in a new environment and context.

Why experienced CEOs may fall for this: Each success reinforces certain patterns. You develop a leadership identity: "I'm the CEO who moves fast" or "I'm the CEO who builds consensus." You may forget that your success came from matching your approach to that specific context.

What changes between CEO roles:

• Industry dynamics  -  Tech moves differently than manufacturing, telecom differently than retail, B2B differently than consumer

• Company lifecycle  -  Turnarounds need different leadership than growth companies or mature market leaders

• Organizational culture  -  What felt like "decisiveness" in one culture looks like "not listening" in another

• Stakeholder complexity  -  Private equity, family shareholders, public markets, and state ownership create completely different dynamics

What to do instead:

• Spend your first 60 days genuinely learning this context before applying your playbook.

• Ask yourself explicitly: "What made me successful last time? Why? What's different here?"

• Find sparring partners in your network who know this industry/context and use them as a sounding board.

• Give yourself permission to lead differently than you did before.

Trap 2: Bringing Your Team With You

The trap: You know certain people from your previous company. They're loyal, you trust them, they know how you work. It's tempting to bring them in.

Sometimes this works. Often it creates problems you might not see until it's too late.

Why this may backfire:

• Your inherited team sees you importing people instead of investing in them. This kills trust before you build it.

• Your imported people don't understand the new culture and make preventable mistakes

• You create an insider/outsider dynamic that takes years to heal

• You miss the chance to learn from people who actually understand this business

One CEO I know brought three executives from his previous company within his first six months. Eighteen months later, two of them had failed or left. The problem wasn't their capability - they were strong leaders. The problem was they never really understood the business, and the existing team never accepted them.

What to do instead:

• Make a list of the roles you're tempted to fill with external hires.

• Ask yourself honestly: "Am I doing this because the internal person can't do the job, or because I'm more comfortable with people I know?"

• If you do bring someone in, do it after you've invested real time in understanding your inherited team's capabilities.

• When you do make external hires, integrate them carefully. Don't give them special status.

Trap 3: Thinking You Have More Time Than You Do

This trap catches even experienced CEOs.

The trap: Your first six months define your tenure - for better or worse.

Yes, you're experienced. Yes, you need to learn the business. But your stakeholders aren't giving you a year to get oriented. They're watching closely from day one.

Your people aren't just evaluating you - they're deciding whether to stay or jump ship. The board that hired you is watching whether their bet was right. Your customers notice the transition.

Why experienced CEOs may miss this: You remember your first CEO role where maybe you got some grace period. Or your last transition went smoothly so you assume this one will too. You overestimate how much patience stakeholders have.

What to do instead:

• Plan your first 30-60-90 days before you start. Don't figure it out on day one.

• Identify 2-3 quick wins for your first 60 days. Not dramatic transformations, just proof points that you can diagnose, decide, and deliver.

• Seriously over-communicate in your first six months. Your people are making up stories about your plans - fight this with clarity and transparency.

Trap 4: Underestimating Your Talent Risk

New CEOs - even experienced ones - often don't realize their arrival triggers an immediate talent crisis.

The trap: Your best people aren't just wondering about you. They're reassessing everything.

People might already be on the lookout for other options. Your arrival either accelerates this or gives them a reason to stay. If you lose 5 critical people in six months, suddenly you're managing a talent crisis instead of executing strategy.

Why experienced CEOs may underestimate this: You might think, "I've managed talent before. I know how to retain people." But you're underestimating the uncertainty you create by your mere presence. The previous CEO - good or bad - was a known quantity. You're not.

When this might lead to a major problem: Departures cluster. When one key person leaves, others start looking. When two leave, it becomes a flood. Knowledge walks out the door. Remaining team members absorb extra work and burn out. Your ability to execute gets damaged just when you're trying to build momentum.

What to do instead:

• Map your 15-20 most critical people in the first month. Not just direct reports - include key technical experts, major client relationship owners, culture carriers.

• Be transparent about your approach and plans. People can handle uncertainty better than vacuum.

• Have proactive retention conversations. Don't wait for them to come to you or worse, for them to resign.

• For your most critical talent, consider retention agreements, expanded roles, or special projects that signal their importance.

Trap 5: Assuming Your Team Is Actually a Team

You inherit what looks like a functional executive team. Everyone's professional in meetings. They're polite to each other. Decisions seem to get made. The meetings run smoothly.

Why this assumption is dangerous: What you're seeing isn’t always teamwork. It might be professional courtesy masking dysfunction. And the team might not be a real team, but a collection of individuals who have learned to coexist.

Your inherited executives might look aligned on the surface, but underneath:

• They barely speak to each other outside formal meetings

• They've learned to avoid conflict rather than resolve it

• Some actively dislike each other but hide it well

• Information doesn't flow between functions - everything goes through you

• They've built fiefdoms, not collaboration

• Real decisions happen in sidebar conversations, not in your meetings

Why experienced CEOs may miss this: You've run teams before. You know what good teamwork looks like. And in meetings, this team seems fine. You have seen much worse in your past engagements. They're not openly hostile. They're not dramatically dysfunctional. They're just... polite.

But polite isn't the same as functional. And what worked for your predecessor - or what they tolerated - isn't necessarily what you need.

What to do instead:

• Test for real collaboration early. Don't just watch how they behave in meetings with you. Watch how they interact when you're not there. Give them a complex problem that requires them to work together and see what happens.

• Have individual conversations. In one-on-ones, ask each executive about the team dynamics. Not "do you all work well together?" but "Tell me about your relationship with [specific peer]. What works? What's difficult?" You'll learn more from these individual conversations than from any team meeting.

• Observe the small moments. How do they interact before and after meetings? Do they ever have lunch together? Do they celebrate each other's wins? Or is it just professional distance?

• Run a team assessment within 60 days. Bring in someone external who can surface real dynamics that won't emerge in normal conversations. You need to know what you're actually working with.

Trap 6: Making Big People Decisions Too Fast

You're experienced. You can read people quickly. You know what good leadership looks like. So when you see someone who isn't working out, your instinct is to move fast.

The trap: Most big people mistakes in the first year come from moving too fast, not too slow.

Why experienced CEOs may fall for this: You've built confidence in your judgment. Maybe you pride yourself on making tough calls. But you're making decisions with incomplete information, and you don't yet understand the full context.

That executive who seems ineffective might be dealing with constraints you don't see. That rising star everyone loves might be politically savvy but operationally weak. That quiet person in the corner might be the technical genius holding everything together.

What to do instead:

• Give yourself 90 days minimum before making major people decisions, unless there's a clear performance crisis.

• Use formal assessments. This de-risks decisions and helps you see things you might miss.

• When you do make changes, make them decisively and respectfully. Don't drag things out once you're certain.

Trap 7: Going It Alone

Here's what experienced CEOs often think: "I've been a CEO before. I know how to handle this. I don't need as much support as a first-timer."

But what many of them forget is that the CEO role is profoundly, uniquely lonely. More lonely than almost any other position in the world. And this doesn't change the second or third time around.

You're surrounded by people all day - in meetings, conversations, events. But you can't be fully honest with anyone in your normal orbit:

• Your board: They're not always your supporters anymore. They're evaluating you constantly, wondering if they made the right choice, considering when your tenure should end. You can't show uncertainty or vulnerability the way you could with a boss in a previous role.

• Your team: They need confidence and clarity from you. They're making career decisions based on their faith in your leadership. You can't share your deepest doubts. And there's always this reality: you're evaluating them too, which fundamentally changes what they'll tell you.

• Your peers in the company: Every conversation has a political dimension. Information travels. People form alliances. You can't think out loud the way you once could.

• Your spouse, partner or friends: They care deeply, but unless they've been a CEO themselves, they often can't fully grasp the specific weight you're carrying.

This isolation is one of the hardest aspects of the role. You're making decisions that affect hundreds or thousands of lives, carrying risks that keep you up at night, navigating complexity that most people can't see - and you're doing it largely alone.

What changes as an experienced CEO: The stakes are higher. The complexity is greater. The scrutiny is more intense. And ironically, people assume you have figured it all out and need less help, so they offer less. If anything, your need for a trusted advisor increases with experience.

What to do instead:

• Set up your advisory support before you start, not after you're drowning.

• This might be an executive coach, a trusted former CEO, an advisor from your industry, or a former boss.

• The specific person matters less than having someone with no agenda except your success.

• Use this person to reality-test your thinking, not just as a therapist.

Trap 8: Overestimating Your Mandate for Change

The conversation that gets you hired goes something like this:

• Board: "We need bold change. We need transformation. We hired you to shake things up."

• You: "I'm ready to drive significant change."

Then you arrive and start making changes. Suddenly you discover the board's tolerance for disruption is much lower than their rhetoric suggested.

Why this trap may catch even experienced CEOs: You've driven change before. You know how to do it. You might even have a reputation as a "change leader." So you assume you have the mandate to move fast.

What you're missing: Every organization has a limited capacity to absorb change. Think of it as political capital - you start with some, and every change costs you some. Spend it all at once and you're broke.

What to do instead:

• Clarify expectations explicitly with each board member individually, not just in the full board meeting.

• Sequence your changes. Everything can't be a priority.

• Build coalitions before announcing major initiatives. Sell your ideas before the formal decision.

• Check in regularly: "Here's what I'm planning. Does this match what you expected when you hired me?"

Trap 9: Neglecting Your Leadership Brand

What experienced CEOs may forget: Every organization you join is a new audience. Even if you have built your reputation as an experienced leader, it doesn't transfer completely. You're building a leadership brand from scratch.

Your first 90 days are when people form lasting impressions of who you are as a leader. Are you approachable or distant? Do you listen or lecture? Do you share credit or take it? Do you handle conflict or avoid it?

The multiplier effect: As CEO, everything you do gets amplified. A casual comment becomes "the CEO said." An offhand decision becomes "the CEO's priority." A bad day becomes "the CEO is angry."

Even experienced CEOs may be shocked to discover how they're perceived. People might talk about them in ways that aren’t remotely the CEO’s self-image.

What to do instead:

• Define explicitly what leadership brand you want to build here.

• Ask for 360-degree feedback at 90 days. Create a safe way for people to tell you how you're actually showing up.

• External stakeholder interviews and independent feedback might give people the safe space they need.

• Be intentional about the culture you're modeling. Your behavior sets the tone much more than your words.

• Remember: Your people are watching everything. Make sure what they see matches what you intend.

Trap 10: Underinvesting in Board Management

Experienced CEOs sometimes think board management is straightforward: prepare good materials, run tight meetings, deliver results.

What this misses: Your board isn't just an oversight body. Each director has their own priorities, their own concerns, their own evaluation of you. Managing them as a group isn't enough.

Some directors care intensely about financial performance. Others obsess about risk and compliance. Some are focused on strategy and long-term positioning. Some want to be deeply involved; others want high-level updates.

What to do instead:

• Invest time in individual relationships with each director. Learn their priorities and communication preferences.

• Never surprise your board with bad news in meetings. Pre-wire difficult conversations.

• Turn board meetings from reports into working sessions. Use your board's expertise, don't just present to them.

• Remember: your board is continuously evaluating whether hiring you was the right decision. Manage this actively, not passively.

Trap 11: Ignoring Culture

Another trap even experienced CEOs may fall into: You focus intensely on strategy, operations, and financial performance. Culture seems soft, hard to measure, something you'll get to later.

The reality: Culture and strategy aren't separate things. Culture determines whether your strategy can actually get executed. A misaligned culture will quietly kill your best plans. You may have designed the right strategy. You may have communicated it clearly. And the organization may quietly ignore it - because the existing culture rewards the opposite behaviors.

What to do instead:

• Diagnose your current culture in your first 60 days. Not what leaders say it is - what it actually is.

• Identify 2-3 cultural attributes that need to shift for your strategy to work.

• Be as concrete and specific as possible.

• Use your own decisions and behaviors to reinforce the culture you want. Where you spend time, who you promote, what you celebrate - these shape culture more than speeches.

• Address cultural detractors directly. One toxic leader can undermine everything you're building.

Trap 12: Forgetting You've Changed, Too

What experienced CEOs often don’t think about: You're not the same leader you were in your first or second CEO role. Your life circumstances have changed. Your risk tolerance has shifted. Your energy level is different. Your patience might be thinner or deeper.

Maybe you're more financially secure now, so you're less hungry. Or maybe you're more risk-averse because you have more to lose. Maybe you're wiser about picking your battles. Or maybe you're more cynical and less open to input.

What to do instead:

• Reflect honestly: How have I changed as a leader? What does this entail? What do I need to adjust?

• Get input from people who knew you in your previous role. Ask: "What should I watch out for? What might be different about me now?"

• Don't assume you can lead the same way you did five or ten years ago. You can't - and you shouldn't.

In summary

Being an experienced CEO is both an advantage and a liability. You have the knowledge, the pattern recognition, the confidence that comes from having succeeded before. But that same success can make you blind to what's different this time.

The best second and third-time CEOs are humble enough to know that each CEO role is genuinely new. They don't coast on their experience. They bring their hard-won wisdom, but they also bring genuine curiosity about what they need to learn and adjust.

Your first six months will be among the most consequential for your success in the role. The good news: these traps are avoidable. With the right preparation, support structures, and mindset, you can navigate your transition successfully and build a foundation for another strong tenure.

The good news: these traps are avoidable. With the right preparation, support structures, and mindset, you can navigate your transition successfully and build a foundation for another strong tenure.

The question isn't whether you have the capability. The question is whether you'll give yourself the support and structure to succeed - or whether you'll assume your experience is enough.

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 ABOUT THE AUTHOR

• Marion Heil is the founder and managing director of Board+CEO Advisors. She is based in Vienna.

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If you're navigating a CEO transition and want a confidential conversation about your specific situation, reach out. After many years of working with executives through transitions, we've learned that the best leaders are the ones who seek input, not the ones who assume they have all the answers.