The career path to CEO exposes every gap you have been hiding. Levi King, CEO and Chairman of Nav, found this out when he ran an anonymous 360-degree feedback survey across all 100 of his employees and discovered the distance between his own self-image and how his team actually perceived his executive leadership. Glenn Gow, The Scaling Executive Coach, sees this pattern in nearly every engagement. The CEO seat goes to the executive willing to close that gap in public.
Quick Answer
The biggest mistakes executives make on the path to CEO come down to four patterns: staying in the “doer” identity when the role demands a leader, letting ego block feedback that reveals real perception gaps, performing confidence instead of sharing honest failures, and assuming functional excellence will grant access to senior decision-making without intentionally building those relationships. Glenn Gow has coached executives through all four of these traps. The ones who reach the CEO seat fastest are the ones willing to make their blind spots visible to the people they lead – not manageable in private.
The “Doer” Trap Stalls More Careers Than Any Skills Gap
The habits that earn early promotions will hold you back from the CEO seat. In my coaching work, I see this more than any other pattern: the higher an executive climbs on the strength of individual execution, the harder the transition to leading at scale becomes. What worked inside a function – doing more than everyone else, solving problems personally, staying in the details – turns into a ceiling the moment the role demands you lead through others.
Karla Johnson, CEO of Pennsylvania Leadership Charter School, ran her first leadership role believing she had to be “the person out front, the forerunner, the person who did all the things, made sure everything happened, the micromanager. That is what I believed leadership to be.” It took her thirty years to fully reframe it: “Leadership is not how much I can do, but it is how much I can get done with the use of my entire team.”
Michael Cherney, Co-Founder and CEO of Cooler Logistics, ran into the same wall as a first-time manager. When he moved to Los Angeles to open a new office, he operated like a lone executor. “I honestly was probably a terrible manager, but I tried to do everything by myself,” he says. The realization came painfully: “I stumbled so often that when I had a moment to take a step back, the greatest opportunities for success were when I needed to ask for help.”
The pattern is hard to break because the behavior was once rewarded. Organizations promote people who execute. The move into executive leadership is the moment when individual execution stops being your asset and starts being your liability. I tell executives: every hour you spend doing the work is an hour you are not spending on the people, strategy, and alignment that define what the CEO actually does.
Jeff Perkins, CEO of Soundstripe, describes the specific challenge of releasing tactical work – demos, press conversations, high-touch customer calls – as he scaled: “I think what has been very hard for me as I’ve scaled up as a CEO is really letting go of some of those things and having the trust in the team that they’re going to execute at a very high level without me kind of being in the room.” He also learned that keeping the wrong people too long is the same trap in a different form. A former boss told him: “I’ve never fired someone and said after the fact, I wish I waited longer. You usually realize that I should have made that call a lot sooner.”
Bryan House, CEO of Elastic Path, names the structural shift that separates a functional leader from a CEO-ready executive. His edge came from learning to leave his lane: “One of the strengths I’ve always had in businesses is my ability to take off my functional hat and sort of wear the CEO hat.” He describes the questions that define CEO-level thinking: “How do you think about who do you need to be bought into the decision? Who do you need to be supportive? Where do you actually need the advocates for whatever direction you think the business needs to go?”
| Behavior | Doer Mindset | Leader Mindset | Downstream Outcome for the CEO |
| Problem-solving | You solve it personally | You build the team that solves it | Scales past your individual capacity |
| Delegation | Reluctant – trust must be earned first | Active – trust is given, then verified | Team executes without you in the room |
| Cross-functional view | Stays in the functional lane | Thinks across the whole business | Builds the advocates needed to move strategy |
| Measure of success | What you accomplish | What the team accomplishes | Growth that survives your absence |
The Ego and Perception Gap
Confidence is what gets you to the top of a function. I coach executives who are still running on the same confidence that earned them their first VP title, completely unaware that the C-suite is measuring something different. The decisive force of will that drove early career success can harden into a wall against the feedback that would actually move the career forward.
Bryan Murphy, CEO of Smartling, ran into this three weeks after joining eBay. A senior HR executive called him in, took him to lunch, and told him directly: “You’ve got a lot of potential, but you’ve got a lot to learn.” Bryan traces the root of the problem to the exact qualities that build strong executives: “You’ve got to be decisive. You’ve got to be a great listener. You’ve got to have a force of will. So sometimes that hardens you up and you may develop a reluctance to change. And that’s probably one of the things, that’s a blind spot that all CEOs tend to have.”
Levi hit the same wall at Nav. The instrument was a structured anonymous 360-degree feedback survey – the anonymity removes the social cost from the respondent and places it usefully on the leader who needs the information. The feedback was not constructive – it was severe. “These are people that just ate me alive in a review that all of a sudden now are rooting for me. Like they wanted me to win, right? Like I’m leading the company they work for. And so that was a huge, huge life lesson.”
Andy Vaughn, President and CEO of Alliant International University, had no idea how far his executive presence was from what the top role required until his boss George said it directly: “George first put it in my mind. He said, Hey, I need you to start looking like a CEO, acting like a CEO, and walking like a CEO.”
Most executives on the path to CEO never get this feedback. They keep performing at the level their peers saw them five years ago, while the people above them measure against a completely different standard. The feedback loop breaks when people learn that honesty carries no upside. I work with executives who have held VP and SVP titles for years while carrying perception gaps their direct reports quietly stopped volunteering to close. The anonymous survey Levi ran works precisely because it removes the social cost from the person giving the feedback and puts the burden – usefully – back on the person who needs it most.
Transparency Builds Trust Faster Than Performance
Most executives on the path to CEO try to project confidence and control at all times. In nearly every coaching conversation, I see the same pattern: the image is carefully managed, and the team is left guessing what is real. The executives who move fastest are the ones who share what they got wrong rather than protecting what they got right.
Levi describes sharing the brutal results of his 360-degree review with his whole company as an act of closing the gap between how he saw himself and how his team actually saw him: “Really trying to see how other people perceive us and our perspective to try to close that gap with especially people on our team so that we’re all rolling in the same direction, not think we’re rolling in the same direction.” The survey that could have damaged his credibility made his employees root for him instead.
John Volturo, CEO of Evolution, spent years performing instead of leading. He calls it a “swirl” – “just constantly worrying about everything I was doing. Was it the right decision? Am I aligning the team around the right things?” He eventually recognized how much energy was going to the wrong place: “A lot of the time I spent doing things that were just trying to prove that I could be successful in what I was doing and prove that I should belong in the job. That was wasted time.” The question John now asks himself: “Are you doing this for the external validation? Are you doing this because it’s the right thing to do and will advance the organization, the company and your team?” The shift he built from that question became the foundation of his Prove Nothing framework – the idea that dropping the need for external validation is not a performance drop, but an unlock that creates space for the decisions that actually move the company forward.
Jeff Helfgott, CEO of Boardroom Salon for Men, learned that context shapes how transparency lands. Early in his corporate career, he walked into his boss’s office and admitted he had made a mistake. His boss laughed: “I’ve been a Vice President here for over 15 years and I’ve never had a Manager come in and tell me that they made a mistake.” His boss followed with a warning: “You are coming from a place where people are deeply connected and involved. That’s not a regular company culture.” The operative principle is to read the cultural environment first, then err toward honesty anyway – because the alignment cost of performing certainty you do not have will eventually outrun the short-term risk of admitting it.
In my coaching work, the cost of performing shows up the same way every time. Every time you project certainty you do not have, every time you hide a mistake that could teach your team something, you are trading your image for their trust. And trust, at the CEO level, is the only currency that actually scales.
Every executive on the career path to CEO faces this environment question. The cultures that reward transparency are not universal. From my coaching work, the executives who advance fastest read the room first, then choose transparency anyway – because performing a polished leadership persona your team does not believe will cost you the alignment you need to execute at scale.
Engineered Proximity: Getting Close Before You Get the Seat
Functional excellence gets you noticed. In my work with aspiring CEOs, I consistently see proximity to senior decision-making as the most underestimated variable on the path to CEO. Executives assume that performing well in their current role will naturally surface them for the top job. It rarely does on its own. The path runs through the rooms where strategy gets made, not through the execution that happens afterward.
Canay Deniz, CEO and Co-founder of Ren Systems, credits his readiness to an intentional early career move – taking a role at a high-growth startup where he could stay close to the founders: “I was actually very close to the founders and the founder CEO of that business and learned a lot along the way. I was close to board meetings and decisions and funding rounds. So I was close enough just to see and observe and get a sense of what it is without really being in the driver’s seat.”
Bryan House, CEO of Elastic Path, made the same move through a different role. His time as Chief of Staff was the position that gave him the view the CEO seat requires. He describes what that position demanded: “How do you think about who do you need to be bought into the decision? Who do you need to be supportive? Where do you actually need the advocates for whatever direction you think the business needs to go?”
Canay’s move was deliberate. He traded a cleaner title for access to decisions that would teach him more. Bryan made a similar trade – lower in the org chart than some peers in one respect, but closer to the conversations that shaped the whole company. The executives who reach the CEO seat fastest usually made one of these bets early.
I watch executives build deep expertise inside a single function for years, then wonder why the CEO role went to someone who appeared less technically skilled. The answer is almost always relationship breadth and strategic visibility. You do not reach the top by being the best individual contributor in the room. You reach it by learning how the room operates.
Frequently Asked Questions
What is the biggest mistake executives make on the path to the CEO seat?
The most common mistake is holding on to the “doer” identity for too long. Glenn Gow sees this pattern across his coaching practice: the behaviors that earned early promotions – individual execution, solving problems personally, staying in the details – become the ceiling that blocks the move to the top seat. Karla Johnson, CEO of Pennsylvania Leadership Charter School, ran her first leadership role as a micromanager before realizing after thirty years that leadership is about what the team accomplishes, not what you accomplish. The executives who stall just below CEO are almost always still measuring themselves on personal output.
How do I get honest feedback about how I’m actually perceived as an executive?
Ask for it explicitly and anonymously. Glenn Gow recommends structured 360-degree feedback because peer and subordinate perception is where most blind spots live, and people will not volunteer that feedback face to face. Levi King, CEO of Nav, ran this process across all 100 of his employees and discovered a massive gap between his self-assessment and his team’s actual view of his leadership. The results were severe. Sharing them openly with his company turned the feedback into a trust-building moment rather than a credibility crisis.
How does ego block executives from reaching the CEO seat?
Ego hardens in proportion to success. Glenn Gow coaches executives to audit their own feedback structures annually – not waiting for a performance review or a crisis to surface the gap. Bryan Murphy, CEO of Smartling, describes what happens when the force of will required to reach the C-suite hardens into a reluctance to change – a blind spot he traces to the decisive qualities that built his career in the first place. The executives who move past this are the ones who build deliberate structures for honest feedback before they need them, not after a crisis forces it.
Should executives be transparent about their failures and weaknesses?
Yes – with attention to context. Glenn Gow coaches executives to share failures and perception gaps directly with their teams, because the trust it produces is faster and deeper than anything a polished leadership persona generates. Levi King, CEO of Nav, shared his entire 360-degree feedback results with his employees and found his team started actively rooting for his success. However, Jeff Helfgott, CEO of Boardroom Salon for Men, learned early in his corporate career that some organizational cultures treat voluntary admission of mistakes as a sign of weakness. Read the environment, then err toward honesty.
What does executive presence actually mean, and how do I develop it?
Executive presence is how you appear to the people above and below you when you are not consciously trying to make an impression. Andy Vaughn, President and CEO of Alliant International University, had a mentor tell him directly that he needed to start moving and carrying himself in a way that matched the CEO role before it happened on its own. Glenn Gow’s position is that executive presence is not performance – it is the visible alignment between your stated values and your daily behavior. Executives still performing for validation have not closed that alignment gap yet.
How do I build the relationships needed to reach the CEO seat?
Get close to senior decision-making before you are the one making the decisions. Canay Deniz, CEO of Ren Systems, credits early access to board meetings, funding decisions, and founder conversations as the preparation that made the CEO role manageable when he stepped into it. Glenn Gow consistently sees executives underestimate how much the top job depends on having built relationships with board members, investors, and cross-functional leaders before the appointment – not after.
How do I let go of execution and delegate as I scale toward the CEO seat?
Start by accepting that your presence in every decision is a bottleneck. Glenn Gow coaches executives to measure their leadership not by their own output but by the quality of decisions their teams make without them. Jeff Perkins, CEO of Soundstripe, describes the specific challenge of releasing high-stakes tactical work as a matter of building trust in the team’s execution, not just stepping back. Build that trust through deliberate feedback loops that show you what the team does when you are not in the room.
What is the difference between a leader and a doer, and why does it matter for the CEO role?
A doer measures success by personal output. A leader measures it by what the team produces. The difference matters because no individual – regardless of how productive – will build a company that scales past their own capacity. Michael Cherney, CEO of Cooler Logistics, admits he was probably a terrible manager as a first-time office leader because he operated as a lone executor. Glenn Gow sees this mistake most often in executives promoted from deep functional roles, where individual excellence was the primary criterion for advancement.
How do I develop the cross-functional thinking the CEO role requires?
Take roles that require you to operate across functions, not just within one. Bryan House, CEO of Elastic Path, found that his Chief of Staff experience was the single assignment that forced him out of his functional lane and into CEO-level thinking – specifically, how to build alignment and advocacy across the whole business. Glenn Gow advises executives who want the top role to seek out assignments that demand cross-functional buy-in. If you have never had to convince someone outside your function to change direction, you are not yet operating at CEO scale.
Why do some executives stall just below the CEO level for years?
Usually because they are performing for external validation instead of building organizational trust. John Volturo, CEO of Evolution, spent years trapped in a cycle he calls a “swirl” – constantly questioning his decisions and trying to prove he deserved the job rather than focusing on what would move the company forward. Glenn Gow sees the same pattern repeatedly: executives who fixate on how decisions look rather than what the decisions will produce. The shift out of that cycle starts with one question – am I doing this for external validation, or because it will actually advance the organization?
How do I know if I am ready to become CEO?
Readiness for the CEO seat rarely announces itself. Glenn Gow coaches executives to measure readiness by three signals: whether your team executes at a high level without you in the room, whether you have built relationships across the business that give you honest feedback, and whether you are making decisions based on what the organization needs rather than what proves you belong. Andy Vaughn, President and CEO of Alliant International University, did not know he was ready until a mentor pointed out the gap between where he was and what the role actually required. Readiness is not a feeling. It is a set of observable conditions – most of which involve how well the people around you operate, not how well you perform.
What is the difference between a VP’s job and a CEO’s job?
A VP owns a function and is accountable for its output. A CEO owns the whole business and is accountable for what every function produces together. Glenn Gow sees this scope shift as the one executives are least prepared for: a VP who misses a target can escalate to the CEO. The CEO has no one to escalate to. Bryan House, CEO of Elastic Path, describes what this demands in practice – the ability to think across every function simultaneously and build alignment where none exists, rather than executing within a defined lane. The job is not harder in degree. It is different in kind.
What You Do Next
Every gap I have described here – the doer trap, the perception blind spot, the fear of transparency, the missing proximity – is fixable. But fixing it from inside the same system that created the gap is slow, and the CEO seat does not wait. Glenn Gow works directly with executives who are serious about reaching the top job and building the kind of leadership credibility that makes people want to follow them. If you are ready to close the gap between where you are and where the seat is, schedule time with Glenn directly to start that conversation.
