You know what got you here won’t get you there when the habits that built your company start slowing it down. Asad Zaman, CEO of Sales Talent Agency, has placed talent inside more than 1,500 companies, from Salesforce to SAP to high-growth startups. He told me his team needed fewer people as it scaled, but the bar for each hire rose and the room for mistakes shrank close to zero.
Quick Answer
You know what got you here won’t get you there the moment the instincts that built your company start blocking its growth. Glenn Gow, The Scaling Executive Coach, sees this same pattern in nearly every founder he coaches: the engineer who will not stop coding, the salesperson who will not stop selling, the operator who will not delegate. The fix is not more effort. It is a lower personal execution standard, so your team moves faster than you ever could alone. CEOs who make this shift report faster decisions, wider ownership, and fewer bottlenecks within months, not years.
The Signs You’ve Hit the Ceiling
A daily to-do list is the clearest warning sign a CEO has become the bottleneck. Steven Monterroso, CEO of ShareVault, told me: “If I’m working off of a to-do list and every day I’m just coming in trying to get through that to-do list, that’s a problem.” Steven came up through sales, where more hours produce more calls and more calls produce more deals. He said that instinct breaks once you run a company: “You can’t outwork bad processes, bad systems. It’s more hours equals more sales, but you can’t run a business that way.”
Physical exhaustion is a signal too. Asad told me: “Yesterday I had nine hours of back to back meetings and I woke up today and I felt it, in a way that I wouldn’t before. If I try to just do things the way I could do them before, I’ll probably fail.” Asad’s agency has helped place talent behind more than 550 million dollars in salaries, and he said the hiring bar for every placement keeps climbing as headcount drops: “We need less people, but we need really good people. Our bar for talent has moved higher and our ability to make mistakes has reduced as well.”
Customer and employee experience decline before most CEOs notice. Michael Cherney, CEO of Cooler Logistics, told me: “In a previous world, as we scaled really fast, we started to cut corners and you could see the cracks. Customer experience wasn’t as good. The employee experience started to deteriorate.” His team spent months building formal processes and training every employee on them.
Josh Fairbairn, CEO of Morpho MFG, hit this ceiling with a hundred customers in year one. He told me: “I’m a dropout. I don’t know what I’m doing. I was just kind of figuring it out fine by the seat of my pants, and I realized I needed some help.” He said the fix was hiring people who could build the systems he never had: “What systems did I make? None. What did I do that made it work for us? Hiring people that could do the things that I couldn’t.”
Some CEOs recognize they need outside help entirely. Michael told me: “I am a completely different person, leader and personally than I was day one. I’ve been fortunate enough to work with an executive coach on a weekly basis, and for me, being humble enough to know that there’s so much that I don’t know, and there’s still so much I need to learn.” Glenn Gow tells clients that admitting what you still don’t know is the fastest way to get coaching that actually works.
Glenn Gow tracks these signals with every CEO he coaches through The Scaling Executive Podcast: a full calendar of meetings, a personal to-do list that never empties, and a team that waits for sign-off before moving. Any one of the three shows up on the guest list above, and Glenn Gow says the fix always starts with the CEO, not the team.
The Imperfect Speed Rule
Chasing 100 percent execution is what turns a CEO into a bottleneck. Steven Monterroso built a rule around this: get to 80 or 90 percent, and let the last 10 percent go. He told me: “Can my team get us 80%, 90% of the way, and can I live with the other 10% miss? By thinking that way, what happens is you end up unlocking your departments and your teams. Executing quicker is a lot more important than being bottlenecked by a CEO.” Glenn Gow tells the CEOs he coaches to set that threshold explicitly, in writing, so their teams stop waiting for sign-off on decisions that do not need it. He has watched the rule fail when a CEO only says it once. He tells clients to put it in writing, share it at the next all-hands, and repeat it every quarter until people stop checking with the CEO before they act.
Your Superpower Becomes Your Ceiling
Kim Hansen, CEO of Cake Equity, kept coding on his own platform long after the company needed him somewhere else. He told me: “I had an advisor that I really trust, and he finally told me, stop coding now. I needed to hear that so strongly and clear to make that shift. I feel productive programming, I can see things coming out of my hands, but ultimately I was letting the team down on important business things and finances and decisions that needed to be made.” Kim said the pattern shows up everywhere: “Often the things that are our strengths are also our weaknesses. You’re sharing an example to your team that you’re making results happen, but you also have to know when is the time to let go of that.”
Bryan House, CEO of Elastic Path, faced the same problem with product strategy. He told me: “Being a functional leader for so long, you sort of own your business, you are down in the details and the weeds. The biggest transition for me moving into the CEO seat was letting go of those reins.” Bryan handed account expansion to his customer success team and put them on a quota instead of leaving it with sales reps. Expansion revenue grew 50 percent year over year the following quarter.
Dan Turner, CEO of Xperigo, described the same instinct in his own words: “I was used to really owning everything, being a doer of a lot of things, relying on myself to get the job done. When I became CEO, I realized I couldn’t be effective if I was going to continue to try to own everything.” Dan said an internal survey found 89 percent of his team agreed.
Dan said the number stuck with him. He grounded the transition in a question his team still uses six years later: “What would Dan do, right? Not what would the CEO of this company do. What would Dan do?” He said he still hears it “quite frequently” from the people who report to him now.
Scaling Is Subtraction, Not Addition
Mark Seeger, CEO of Glydways, spent eleven years shedding the technical identity that built his company. He told me: “The skills that got me the job are absolutely not the skills that will allow this enterprise to scale. Over the last eleven years, I’ve had to shed and let go all these things I just spent decades learning and getting diplomas for.” Mark said the change is not additive: “Be prepared to change your identity. It’s not one of adding. You’re gonna be subtracting a lot of the things you brought into the journey.”
Sameer Ahuja, President of GameChanger, scaled the company from under 10 million dollars to more than 100 million in annual revenue. He told me the early playbook has to go: “You absolutely need to shed every element of ego that you have. Each phase is so different, and you have to ignore what got you here and completely commit to a new version of yourself.”
Sameer said the hardest part is ignoring your own highlight reel. He told me: “Any success that you have, maybe you had success building an MVP, maybe getting early product market fit, early capital, each phase is so different.”
Sheldon Fernandez, CEO of DarwinAI, spent 16 years as a CTO before taking the top seat. He told me the line his own former CEO gave him: “That which makes you good will keep you from being great.” Sheldon spent his first year as CEO learning board management and operational reporting instead of writing product specs, the two skills furthest from what made him a strong CTO.
Two Ways CEOs Let Go
CEOs split into two camps once they decide to hand off control, and they disagree on how far to go. Mark Seeger argues for full removal. He wants the company to run without him, as a system that keeps learning in his absence. Michael Cherney disagrees. He believes scaling demands the CEO’s direct hand in designing and training the team on the processes that keep quality from breaking down as the company grows. Neither approach is wrong on its own. Glenn Gow tells clients to pick the one that matches how their company actually breaks under growth, not the one that sounds better in a book.
| Approach | What the CEO Does | What It Produces |
| Full removal (Mark Seeger) | Steps back entirely so the company runs as a system that keeps learning without him | An organization that scales without waiting on the founder |
| Process architecture (Michael Cherney) | Personally designs and trains the team on formal processes | Consistent quality and experience as headcount grows |
Ego, Advice, and the Certainty Trap
Tom Chavez, CEO of SuperSet and former CEO of Krux and Rapt, said ego is the single word that explains why CEOs fail to scale. He told me: “Ego is the enemy of progress. The CEOs who fail to scale become too certain. I like to talk about the certainty to knowledge ratio. I see so many CEOs with a ratio there that’s hopelessly out of control.”
Sameer Ahuja calls this staying selfish about advice. He told me: “You have to be selfish with asking for advice. When they tell you something, it sounds so foreign, you’re like, there’s no way that this makes sense. But you have to be completely open-minded to a new approach.”
Stop Proving, Start Deciding
John Volturo, executive coach and former C-suite leader, said the drive to prove yourself is the trap most CEOs never name. He told me: “We’re constantly trying to prove that we can get the job done. That external validation is draining because we end up performing all the time. The shift was to prove nothing.” John now coaches C-suite executives through the same shift after surviving a brain tumor that forced him out of a performance-driven leadership style.
Glenn Gow builds this question into the first working session with every new CEO client: which habit from the last twelve months still works, and which one only worked because the company was smaller. It rarely takes one conversation to find the answer, but it always starts there.
FAQ
What does “what got you here won’t get you there” mean for a CEO?
It means the habits that built your success are the exact ones now slowing you down. Tom says the fix is showing up every day and relearning fundamentals as if you were new: “You gotta be super humble and just go to the shed every day, do your hard pushups and learn, learn, learn.” Glenn Gow tells clients the reputation that got them here means nothing about what gets them to the next stage.
Is “What Got You Here Won’t Get You There” a real book?
Yes. Executive coach Marshall Goldsmith published it in 2007, and it remains one of the most cited leadership books among the CEOs Glenn Gow coaches on The Scaling Executive Podcast. Its core idea, that success habits become failure habits at the next level, matches what shows up across the guests in this article.
What are the 20 habits in “What Got You Here Won’t Get You There”?
Goldsmith’s book outlines 20 interpersonal habits that quietly sabotage successful leaders, things like needing to win every argument or adding your own opinion to every discussion. None of the CEOs Glenn Gow coaches need the full list memorized. The pattern that matters most for scaling founders is different: the habit that trips them up is usually the one thing they used to do best.
What is the fastest way to tell I’ve become the bottleneck in my own company?
Steven, CEO of ShareVault, said a daily to-do list is the clearest sign. If you’re coming in every day just trying to clear it, you’ve become the bottleneck instead of the leader. Josh Fairbairn hit the same ceiling with a hundred customers in his first year, before he’d built any systems to run the business without him.
How much should a CEO delegate before it actually works?
Enough that you can live with a 10 percent miss. Steven built his team around an 80 to 90 percent execution rule instead of demanding perfection from every decision. Asad‘s agency has helped place talent behind more than 550 million dollars in salaries, work he says only scaled once he accepted a smaller personal role in each individual placement.
Does becoming a better CEO mean becoming a completely different person?
CEOs in this article disagree. Mark argues you’re subtracting your old identity, not becoming someone new. Dan Turner had the opposite experience: when he panicked about needing a new CEO persona, his coach told him, “Dan, be yourself,” reminding him the traits that got him the job were still the right ones at a bigger scale. Dan says he still hears that advice six years later.
Should a CEO try to eliminate ego completely?
The guests split on this. Tom and Sameer argue ego makes CEOs too certain to keep learning, and both push leaders to actively seek outside advice. John argues the opposite risk: chasing external validation, trying constantly to prove yourself to others, is just as damaging. Glenn Gow tells clients the answer is neither more certainty nor more proving. It’s checking your assumptions against people who have scaled past where you are.
Why do some executives need to stop trying to prove themselves?
John says most CEOs are rewarded early in their careers for constantly proving they can get things done, and barreling through work becomes the default. He told me the harder skill is stepping back to think about what actually matters and aligning the company around that, instead of grinding through every task alone. Glenn Gow calls this one of the hardest transitions CEOs make, because the habit that got them promoted is the same one that exhausts them at scale.
Does this pattern apply before someone becomes CEO?
Yes. Sheldon spent 16 years as a CTO before he had to make the same shift as CEO of DarwinAI. Mark Seeger says the same shedding process started during his own years as a hands-on product engineer, well before Glydways needed him to lead.
Why do technical founders struggle with this more than other leaders?
The deeper the technical skill, the harder the letting go, because the skill is tied to identity, not just a job description. Kim coded the platform himself before Cake Equity needed him elsewhere. Bryan ran product at Elastic Path before becoming CEO. Mark spent decades earning engineering diplomas before Glydways needed a different kind of leader.
Should a CEO hire an executive coach to make this shift?
It helps. Michael, CEO of Cooler Logistics, worked with an executive coach every week and said it made him a different leader. Glenn Gow says most CEOs try to make this shift alone first, and most come to coaching only after they’ve already hit the wall Michael describes.
How long does it take to unlearn the habits that got you here?
Longer than most CEOs expect. Mark said the process took him eleven years and is still ongoing. Glenn Gow tells clients to treat it as a permanent practice, not a project with an end date.
What You Do Next
Pick one habit from this article that you recognize in yourself this week. Write down your 80 to 90 percent execution threshold and say it out loud to your team before Friday. I’m Glenn Gow, and I coach CEOs through exactly this kind of shift every week. Grab a time on my calendar and bring the habit you’re least sure about.
