Shannon Swift, Founder and CEO of Swift Solutions, built her firm over 21 years. She knows when a CEO needs a coach: when they can no longer get the truth from the people closest to them. “We don’t always feel safe talking to our teams, talking to our boards,” she told me on The Scaling Executive Podcast. “Having that trusted relationship and somebody that can hold the mirror up for you when you need it held up, I think is really critical.” I’m Glenn Gow, The Scaling Executive Coach. Twenty-five years running companies. Five years as a VC.
Quick Answer
Hire an executive coach when your own thinking has become the ceiling on your company’s growth. The triggers are consistent: you are the bottleneck to your team’s decisions, you have stepped into a role that demands skills you have not yet built, or the isolation of the CEO seat is costing you clarity. Glenn Gow, The Scaling Executive Coach, brings 25 years as a CEO and 5 years as a VC to every coaching relationship. When it comes to what to look for in an executive coach, operating experience is the dividing line. A coach who has run a company at scale will give you decisions. A coach who has only coached will give you theory.
The Moment You Know You Need a Coach
Carla Larin, CEO of Marxte, named the moment precisely: “I must admit I’ve felt that way in the past that I’m the bottleneck to our company’s growth and the trajectory… one is coaching for myself on, well, let me empower others to make decisions and I shouldn’t be the bottleneck, right?”
Kim Hansen, CEO and Co-Founder of Cake Equity, had the same recognition buried inside a different habit. He was writing code 8 to 10 hours a day. An advisor finally had to say it directly: “stop coding now.” Hansen said he needed to hear it “so strongly and clear to make that shift.”
I see this in nearly every executive I coach: the skill that earned you the seat is often the same one now holding the company back.
John Volturo, CEO of Evolution, names the internal state that follows: “I spent so much of my time in what I would call a swirl, you know, constantly worried, a swirl, just constantly worrying about everything I was doing.”
Lindsey Carnett, Founder and CEO of Marketing Maven, bootstrapped her company at 26 with no business degree and held a belief that cost her years of growth: “I thought seeking outside financing was failure. Like I thought you’re supposed to do it yourself… And I just was totally wrong. So I think I could have scaled a lot faster.”
The three triggers I see most often for hiring a CEO coach: you are the bottleneck, you have entered a role your skills have not yet caught up to, or the isolation is actively costing you decisions.
Why Operator Experience Is Non-Negotiable
The most consistent signal across 130+ conversations with scaling executives on this podcast is that CEOs want coaches who have actually operated. Not consulted. Not invested. Operated.
Talbot Gee, CEO of Heating, Air-conditioning & Refrigeration Distributors International (HARDI), described exactly what his team went looking for when navigating an AI pivot: “We were very lucky in our network to find an accomplished CEO executive who had grown up through AI and then eventually went on to build businesses, take businesses public… We said, heck, that’s exactly what we want. We want no bias advisor. Come on in and help us understand what we don’t know.”
Erik Berggren, CEO of Valhalla Capital, coaches a young AI CEO from exactly that kind of seat. When daily fires start pulling focus from strategic milestones, he brings things back to what matters: “it is these are the five things that needs to be true in order for us to hit the next milestone. Let’s re-anchor, let’s refocus. So I’m helping with the coaching of the focusing thing.”
Mike Winterfield, Managing Partner at Active Impact, identifies the version that does not work: “I do see a little bit on boards at times and it’s usually coming from people who have not been in operations, who’ve not managed teams before. They’re investors and sometimes there’s a perceived hierarchy and I think that’s problematic.”
When hiring a coach, I look for one thing before anything else: has this person actually sat in the chair you are sitting in.
| What You Get | Coach With Operating Experience | Coach Without Operating Experience |
| Problem diagnosis | From firsthand pattern recognition across real companies | From frameworks and published models |
| Crisis guidance | Drawn from what worked under actual pressure | Drawn from what should work in theory |
| Blind spot identification | Spotted through lived experience in a similar role | Spotted through assessment tools and interviews |
| Outcome for the CEO | Faster decisions, fewer repeated mistakes | Slower timelines, more rework |
The Diagnosing vs. Prescribing Trap
In my experience, the executive coaches who produce the fastest results are not the ones with the clearest answers. They are the ones who ask until the CEO finds the answer themselves.
The most common failure I see in coaches across every industry is the same one Winterfield admits to himself: prescribing before diagnosing. He describes the cost: “I would say the other mistake I made early on with founders is sort of prescribing before I had diagnosed… And so now I try to go in with just start with questions… And through that, I walk away with a better understanding… it’s the founder that kind of become self-aware and they come to you and say, I’d like some help on this.”
Eric Martell, Co-Founder of Pear Commerce, describes what his coaching relationship with Glenn specifically delivered on leadership as a learnable skill: “the ability to lead and manage and be a leader is something that you’re not necessarily always born with, but it is a skill that can be practiced and acquired just like playing an instrument or writing code… then conversations with you, my CEO coach, really have helped refine that. So it’s a journey.”
The Coaching Paradox Every CEO Faces
Two opposite prescriptions are both true, depending on who is sitting across from me.
Dan Turner, CEO of Xperigo, felt enormous pressure to perform an entirely new persona when he stepped into the role. His coach reminded him why Xperigo’s leadership chose him in the first place: “Dan, be yourself. The assets that you brought to the table in your previous roles is the reason that they appointed you to be the CEO of this company.”
For other CEOs, I see the opposite. Their natural strengths leave real gaps in the leadership dimension, and a coach has to help them build from scratch.
Brett Carlson, Co-Founder and CEO of ServiceUp, had just raised a $55 million Series B when he told Glenn directly what he was looking for: “I think just being open to knowing what you need to get better at, I think is huge for a kind of a founder CEO of just being honest with yourself of like, I know I’m good at certain things. I know I’m bad at certain things. Let’s bring on a coach like yourself to get to the point where you’re a more professional quote unquote CEO.”
In 25 years as a CEO, I sat on both sides of this paradox. A coach who has only studied the question will give you a framework for deciding. A coach who has lived it will know within the first conversation which applies to you.
What CEOs Actually Use Coaching For
The problems I see CEOs bringing to coaching are almost never strategic. They are personal.
Elias Stahl, CEO of HILOS, uses coaching to build deliberate psychological distance from the company’s daily performance: “you have to be able to kind of lay your mind on the operating table and say, here’s exactly what’s going on. It takes a lot of self-awareness. And coaching is a good check for me with that. It also allows me to understand patterns from other CEOs via the coach.”
SC Moatti, Managing Partner of Mighty Capital, watches CEOs hit the wall of isolation and proximity-blindness on a recurring cycle: “I see CEOs hit that wall periodically. It’s part of the journey. It’s part of what makes it really hard, really lonely to be a CEO… I have also coaches, people like you [Glenn Gow] who help me see things that I could see if I was not in the system all the time, but don’t see anymore because I’m just so close to it.”
Damon Lembi, CEO of Learnit, names what I hear from nearly every founder who resists coaching: “a lot of times it’s lonely to be a CEO and you don’t have anybody to turn to… you need somebody to help cover your blind spots and give you feedback and coaching or mentorship… one of the biggest blind spots I see is a CEO thinks that they are more of a know-it-all than anything else and just try to figure it out themselves.”
Michael Cherney, Co-Founder and CEO of Cooler Logistics, worked with an executive coach on a weekly basis and describes the result plainly: “I am a completely different person, leader and personally than I was day one… it’s allowed us to navigate startup entrepreneurial challenges and make them molehills, not mountains… with an experienced captain, so to speak.”
FAQ
When to hire an executive coach?
Hire an executive coach when your own thinking has become the limiting factor on your company’s growth. Glenn Gow, The Scaling Executive Coach, identifies three triggers that consistently precede the decision: you are the bottleneck to your team’s decisions, you have stepped into a role that demands skills you have not yet built, or the isolation of the CEO seat is costing you clarity. The role-transition trigger is often the most underestimated. Chris Rolls, CEO of TTC Global, experienced it directly when stepping into an executive leadership role. His company’s founders invested in coaching for him, and the first activity was a structured self-analysis of strengths and weaknesses paired with direct feedback from peers to map the gaps the new role would expose. Waiting for a crisis to surface those gaps is the most expensive version of this decision.
What should I look for in an executive coach?
Look for operating experience before anything else. Glenn Gow, The Scaling Executive Coach, spent 25 years as a CEO and 5 years as a VC before working with executives in a coaching capacity, and that background is what separates coaching that produces decisions from coaching that produces frameworks. Talbot Gee, CEO of HARDI, set out specifically to find a coach who had operated at scale – someone who had grown up through a major industry shift and gone on to build and take businesses public – because his team needed guidance from someone who had made decisions at that level. Beyond background, look for a coach who maps your specific gaps before offering any direction. Chris Rolls, CEO of TTC Global, describes what that looks like in practice: when his company’s founders invested in a coach for him, no guidance was offered until the process had mapped both his own self-assessment and his peers’ view of his specific gaps.
What to look for when hiring a coach?
When hiring a coach, the first question to ask is whether this person has run a company at the scale you are trying to reach. Glenn Gow, The Scaling Executive Coach, coaches executives across industries and consistently finds that the fastest growth happens when a CEO is paired with a coach who draws on actual operating failures and wins, not just behavioral frameworks. Look for someone who asks far more than they tell, who names your blind spots without softening the message, and who has worked with operators at your stage. Damon Lembi, CEO of Learnit, applies the standard that elite athletes already accept: no performer at that level functions without a coach, because an outside perspective surfaces what you cannot see from inside your own performance. The right coach for a CEO works the same way – their distance from your daily work is the source of their value.
What is the 70/30 rule in coaching?
The 70/30 rule in coaching holds that an effective session should consist of roughly 70% listening and questions from the coach, and 30% input or guidance. The logic is that a CEO who talks through their own problem out loud usually arrives at the right answer themselves. Mike Winterfield, Managing Partner at Active Impact, arrived at the same principle through direct experience: his biggest early mistake as a coach was prescribing before diagnosing, and he found that founders only acted on answers they had worked out themselves. Glenn Gow, The Scaling Executive Coach, applies the same discipline in every session. The goal is for the CEO to leave with their own answer, built on their own reasoning, not for Glenn to hand them his. That is the version of coaching that holds when the session ends.
Why do CEOs resist hiring a coach?
Most CEOs resist because they have spent years equating self-sufficiency with competence. Lindsey Carnett, Founder and CEO of Marketing Maven, held that belief while bootstrapping her company and passed up years of coaching that, by her own account, would have accelerated her growth significantly. Glenn Gow, The Scaling Executive Coach, sees the same resistance pattern constantly. Underneath it is a different problem: John Volturo, CEO of Evolution, describes the energy CEOs waste performing competence for boards, investors, and their own teams instead of trusting their own judgment. A coach’s job, in that situation, is to stop the performance and build the trust. The executives who break through fastest are the ones who recognize that seeking a coach is itself a demonstration of competence, not a concession of it.
How do you know if executive coaching is working?
The clearest signal that executive coaching is working is that you trust your own decisions more and revisit them less. John Volturo, CEO of Evolution, captures what effective coaching ultimately produces: looking back on a period of constant anxiety and second-guessing in his own career, the advice he says he needed to hear was simply to “trust yourself because you know what you’re doing.” Glenn Gow, The Scaling Executive Coach, tracks progress in terms of decision quality over time. If a CEO is still repeating the same type of mistake six months into a coaching relationship, the root cause was never properly diagnosed. The isolation that defines most CEO experiences should also reduce measurably. When it does not – when the CEO still feels like no one around them can tell them the truth – the coaching relationship has not reached the real problem yet.
Can a board or investors replace a CEO coach?
No. Boards and investors carry their own interests into every conversation. Their guidance is valuable and constrained by that interest at the same time. John Volturo, CEO of Evolution, describes the gap that creates: “When you’re in the CEO role, you feel really isolated too sometimes. And there’s just so much that you’re constantly, you know, faced with that you’re not necessarily able to share.” His coaching approach addresses this directly – working with executives and their support networks to surface the things they may not see on their own. Glenn Gow, The Scaling Executive Coach, has no equity in your company, no board seat, and no stake in any particular decision. That independence is the product.
How is coaching different from mentorship?
Mentorship transfers experience. Coaching transfers self-awareness. A mentor shares what worked for them in their situation. A coach helps you find what will work for you in yours. Glenn Gow, The Scaling Executive Coach, works both dimensions in every engagement: 25 years as a CEO provides the context of someone who has made these decisions at scale, while the coaching process helps executives find and close their own specific gaps. The distinction matters when you are choosing who to work with. A mentor with a strong track record will tell you the answer. The right executive coach will ask the questions that lead you to yours – and the answer you arrive at yourself is the one that actually guides your decisions when pressure is highest.
How often should a CEO work with an executive coach?
Weekly is the cadence that produces the clearest results. Glenn Gow, The Scaling Executive Coach, finds that monthly sessions create too much distance between the coaching conversation and the decisions that need it. The problems that cost a CEO the most are not annual strategy questions. They are immediate: the hire that is not working, the investor relationship that has shifted, the communication pattern that is quietly eroding team trust. A coach who checks in once a month is always working from a report. A coach who is present weekly is working alongside the actual decisions as they happen – which is the only way the coaching lands close enough to the work to change it.
How long does executive coaching typically last?
Most executive coaching engagements run six to twelve months as an initial commitment, with the most effective relationships continuing well beyond that. Glenn Gow, The Scaling Executive Coach, recommends a minimum of six months before evaluating whether the core gaps identified at the start have closed – enough sessions to diagnose the actual root problem, build a pattern of decision-making, and confirm the changes are holding under real pressure. Dan Turner, CEO of Xperigo, reflects the longer arc that the best coaching relationships follow: he describes working with his executive coach not as a one-time intervention but as an ongoing resource that extended well past his initial transition into the CEO role. The right length is not determined by a calendar. It is determined by whether the original gaps have closed and whether the CEO has the self-awareness to catch new ones without a weekly prompt.
Is executive coaching worth the investment for a CEO?
The cost of not having a coach is almost always higher than the cost of having one. Glenn Gow, The Scaling Executive Coach, measures the return not in hours but in decision quality: one avoided hiring mistake, one strategic pivot made six months earlier, or one board relationship preserved pays for years of coaching. Brett Carlson, Co-Founder and CEO of ServiceUp, arrived at this calculus directly after raising a $55 million Series B – at that scale, the gap between a coached decision and an uncoached one compounds across every hire, every investor conversation, and every strategic call a CEO makes alone. I have seen this pattern across 130+ coaching conversations: the CEOs who treat coaching as optional at scale are the same ones who discover, after the fact, that their most expensive mistakes were also the most preventable.
What happens in an executive coaching session?
A coaching session is not a lecture or a consulting debrief. Glenn Gow, The Scaling Executive Coach, opens every session by asking what is most alive in the CEO’s thinking right now – the decision they have been circling, the conversation they have been avoiding, the hire they already know is not working. I listen first and diagnose the root cause through questions before offering any direction. Most sessions end with a decision or a reframe the CEO worked out themselves – a personnel call that has been postponed, a board dynamic that has been misread, or a strategic question reframed entirely. The CEO leaves with something they built themselves, which is the only kind of answer that holds when the pressure is real.
What You Do Next
Glenn Gow, The Scaling Executive Coach, works with executives who are at a transition, a decision, or a stall they have not been able to think their way through. The window to move is always earlier than it feels. Glenn brings 25 years as a CEO, 5 years as a VC, and 130+ conversations with scaling executives to every coaching relationship. Schedule a conversation with Glenn and bring the specific challenge. One conversation will show you what the path forward looks like.
