Executive coaching helps a leader get better inside a role where someone else still holds the final call. CEO coaching helps a leader carry a role where no one is above them. Joshua Gould, CEO of thebigword, runs a company with more than 400 employees and 15,000 contractors, and he still says the jump from C-suite to CEO was the hardest step of his career.
Quick Answer
Executive coaching sharpens a skill inside a role where someone else still has the final say. CEO coaching rebuilds how a leader operates once no one is left to check their decisions. I’m Glenn Gow, The Scaling Executive Coach, and the clearest signal you need CEO-level coaching is the moment you realize there’s no one to call when something breaks. Executive coaching targets a specific behavior or skill gap. CEO coaching addresses the full structure around a leader: isolation, delegation, and accountability at the top.
What Separates Executive Coaching From CEO Coaching
People searching for CEO coaching vs traditional executive coaching differences are usually trying to solve one problem: which kind of coach actually matches where they sit in the org chart. I judge that by one variable: who catches you when something breaks. Joshua told me the step up from C-suite to CEO surprises almost everyone who makes it. “Even a COO or CTO… you do have a boss. You never have to be alone. And you’re never ultimately responsible for anything, even though you really believe you are. And then one day you become the CEO and there is no one to call in the middle of the night.”
That fact, the one Joshua just described, drives the difference between the two disciplines. I coach executives on skills: delegation, communication, execution. I coach CEOs on structure: who is around them, what they can say out loud, and what happens the first time they make a call with no one to check it against.
Why CEO Isolation Is a Structural Problem, Not a Personal One
I tell every CEO I work with the same thing: isolation at the top is not a sign you are doing the job wrong. It is a feature of the seat itself. Shannon Swift, CEO of Swift Solutions, sees this pattern constantly in her own coaching work. “I think the level of imposter syndrome is really huge. The persona that you see displayed, a whole lot of executives and CEOs are wondering how the hell they got here… people are gonna find out that I don’t really deserve to be here.”
I treat that isolation gap as structural, and building the right people around a CEO closes it faster than any pep talk ever will. John Volturo, CEO of Evolution, builds his entire coaching practice around closing that same gap. “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. And when I work with CEOs and C-suite people, part of what we do is work with their support network.”
I see the same pattern show up with nearly every CEO I coach in their first year in the seat. The problems that used to get solved in a hallway conversation with a boss now sit on the CEO’s desk alone, and no amount of experience running a department prepares a person for that shift overnight.
Executive Coaching vs CEO Coaching: A Side-by-Side Look
Since the two disciplines solve different problems, they produce different outcomes for the CEO who picks the right one. Here is how I break it down for the leaders I coach.
| Factor | Executive Coaching | CEO Coaching |
| Who it’s for | VPs, department heads, and C-suite executives who still report to someone above them | CEOs and founders who sit at the top of the org chart with no one to escalate to |
| Primary focus | Sharpening a specific skill or behavior inside an existing role | Rebuilding how a leader operates once no one is checking their decisions |
| Typical trigger point | A performance review, a promotion, or a skill gap a manager flags | The isolation, stalled delegation, or burnout that shows up after taking the top seat |
| What it produces | A stronger executive who performs better inside the current structure | A CEO who scales the company instead of becoming its bottleneck |
The Doer-to-Delegator Trap Every Scaling CEO Hits
Jim Schleckser, CEO of The CEO Project, has coached hundreds of founders through this exact wall. He says the trap starts with the skill that got you promoted in the first place. “As we grow the business, we have something that we’re excellent at. Marketing, engineering, sales, name it, whatever your gift is, and everybody has a gift. And as you grow the company, you keep contributing in this way. And eventually, you really should hire somebody to replace yourself in that job.”
Jim puts a specific cost on what happens when a CEO refuses to let go of that job: the company ends up paying for a full CEO while getting the output of a VP of sales. His fix is a rule he uses with every client. “I believe we should be ruthless about delegation… We have a rule we call the 70% rule… The idea is if somebody 70% as good as you are at a task, delegate it immediately.”
Chris Rolls, CEO of TTC Global, names the same pattern from the inside of his own transition. “Most people I see who are CEOs, who are ambitious, who want to grow, they also kind of think they’re Superman or Superwoman. And you try and do everything yourself. And I think the biggest insight that I had that helped me was understanding that I couldn’t be everything at all times.” Chris credits a formal coaching engagement, paid for by his company’s founders, with breaking that habit. “One of the things that I was very thankful for is that the founders invested in me. And I worked up a CEO coach. And one of the activities we went through was both a self analysis of where my strengths and weaknesses are, but also an analysis from my peers.”
Dan Turner, CEO of Xperigo, hit the same wall moving from COO to CEO. “I was used to really owning everything and being a doer of a lot of things… but when I became into the especially the CEO role, and being in charge of an entire organization, I realized that I couldn’t be effective if I was gonna continue to kind of [do that].” Dan still works with the executive coach who helped him make that shift.
Carla Larin, CEO of Marxte, describes the same trap from the founder’s chair. “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.”
The “Prove It” Cycle That Burns Out Executives
John Volturo separates functional executives from CEOs by watching what drives them day to day. “Most people I know, most executives I work with, whether they’re like you said, CEO, C-suite… feel like they’re in a constant proving mode. And it’s in part because we live in this culture that wants us to win.” John says that same reward system pushes executives toward constant busyness instead of the reflection a CEO role actually requires.
Brett Carlson, CEO of ServiceUp, tells founders the honest version of this same lesson. “One of the big things of not getting yourself fired as you evolve your own company… is just being open to knowing what you need to get better at… Let’s bring on a coach like yourself to get to the point where you’re a more professional quote unquote CEO.” Brett names the one skill he considers non-negotiable past a certain size. “The one thing that you cannot be bad at in being a CEO is as you scale past 20 people is you have to be able to manage effectively.”
Building the Support Network That Replaces the 3 AM Problem
Joshua Gould solves his own isolation problem in a way most CEOs would never try. He treats his investors as an unfiltered sounding board instead of an audience to impress. “I drive my investors mad because most CEOs will only give a very polished view of the world to their investors. But I actually treat my investors like I treated my father when he was the chairman of the company. Part shrink, part coach.”
Michael Cherney, CEO of Cooler Logistics, built his support network around a formal weekly coaching relationship instead. “I’ve been fortunate enough to work with an executive coach… from, you know, on a weekly basis. And it’s allowed us to navigate startup entrepreneurial challenges and make them Mo Hills, not mountains.”
I put my own CEOs through the same exercise. Pick your coach, pick your investors or board, and pick two or three peers who run companies at your scale. That’s the network that catches you the night something breaks, instead of leaving you to solve it alone at your desk.
How to Choose the Right Fit for Where You Are
If you still have a boss, or a board member who can override your call, you likely need executive coaching aimed at a specific skill gap. If you are the last stop for every hard decision in your company, you need CEO coaching built around isolation, delegation, and accountability. I’ve watched Shannon Swift’s CEO clients make that switch the moment they stopped having anyone above them to answer to.
I tell CEOs the move from one to the other comes down to a single question: does anyone still stand between you and the outcome? Once that person disappears, the coaching has to change with it.
Ask yourself three questions before you hire either kind of coach. First, who currently has the authority to override a decision you make this week? If someone does, you are still an executive, and a skill-focused coach will serve you well. Second, when something goes wrong at 11 PM, who is on your call list? If the honest answer is no one, that gap is the first thing a CEO coach should help you close. Third, are you still doing the job that got you promoted, or are you running the whole company? Jim Schleckser built an entire coaching practice around CEOs who answer that third question the wrong way.
None of this requires picking one relationship and sticking with it forever. Joshua Gould leans on investors. Michael Cherney leans on a weekly executive coach. Chris Rolls leans on a coach paired with peer feedback. Carla Larin leans on both a coach and her own team. The format changes. What stays constant is the decision to build the network before the isolation of the seat catches up with you.
I ask every CEO I onboard to name the three people they would call first if a deal fell apart at midnight. Most cannot answer immediately. That pause is the entire argument for building this network on purpose instead of waiting for a crisis to force the issue.
Frequently Asked Questions
What is the difference between executive coaching and CEO coaching?
Executive coaching sharpens a skill inside a role where someone else still signs off on the outcome. CEO coaching rebuilds how a leader operates once no one signs off on anything. John Volturo, CEO of Evolution, puts the practical difference this way: for most CEOs he coaches, the work is “stepping back and thinking about what it is that we’re really doing and aligning everything around us toward that end,” instead of just proving they can execute. I’m Glenn Gow, and I walk every CEO client through that exact stepping-back exercise in their first ninety days.
Is a CEO coach different from a business coach?
A business coach often works on the mechanics of running a company: pricing, operations, hiring systems. A CEO coach works on the person carrying those decisions alone. Michael Cherney, CEO of Cooler Logistics, says the value of his weekly coaching relationship only holds up when he stays “humble enough to know that there’s so much that I don’t know,” and pairs the coaching with what he learns from his own team. Glenn Gow builds that same humility check into every coaching engagement.
When should an executive move from executive coaching to CEO coaching?
The trigger is the day you stop having anyone above you to escalate to. Dan Turner, CEO of Xperigo, got direct advice from his coach the moment that hit him. His own board had just appointed him CEO on the strength of the same track record he was now doubting: “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.” Glenn Gow tells his clients that advice works because it treats the promotion as evidence, not an accident.
Does a CEO coach need to have been a CEO themselves?
Not always, but the strongest CEO coaches understand the isolation of the seat firsthand or have coached enough CEOs to recognize the pattern instantly. Jim Schleckser, CEO of The CEO Project, built his coaching model around a specific financial insight most CEOs miss: when a CEO keeps doing a VP-level job instead of hiring for it, “it’s the cheapest CEO you’re ever going to hire.” Glenn Gow sees that insight land hardest with CEOs who came up through sales or engineering.
What does an executive coach do that a CEO coach doesn’t, and vice versa?
An executive coach typically targets one behavior: a communication style, a delegation habit, a leadership blind spot. A CEO coach works across the entire operating system of the role. Carla Larin, CEO of Marxte, describes that broader work directly: “Whether it’s through a coach or whether it’s through getting feedback from peers, making sure that as a leader, you empower your teammates to make their own decisions and have autonomy and decision-making authority to be able to push things forward independently.” Glenn Gow asks every CEO client which three decisions they could hand off this quarter using that same standard.
Why do so many CEOs experience imposter syndrome?
Because the isolation of the seat leaves no natural place to test whether their doubts are normal. Shannon Swift, CEO of Swift Solutions, calls having a coach “really, really a vital aspect of any, not only a CEO, but any executive’s journey,” specifically because it gives leaders a place to admit doubts they can’t raise anywhere else in the company: “someone that you feel really safe in having those conversations.” Glenn Gow builds confidentiality into every CEO coaching engagement for exactly this reason.
Is it okay to use investors as an informal coaching resource?
It works for some CEOs and backfires for others, and the difference comes down to one test. Glenn Gow tells clients this only works if they are already sharing unfiltered numbers and bad news with that investor today. If the current relationship still involves a polished version of the business, building that level of trust takes longer than simply hiring a coach who starts from zero.
What’s the biggest mistake CEOs make when choosing between the two types of coaching?
Hiring an executive coach to fix a delegation habit when the actual problem is structural: no one else in the company has the authority to make a final call. A skill-focused coach cannot fix that gap. Glenn Gow sees this mismatch constantly with founders who scaled fast and never rebuilt who holds decision-making power beneath them. CEO coaching solves it by redistributing authority across the company, not by sharpening one behavior.
Is CEO coaching worth the investment?
Glenn Gow measures the return on CEO coaching in decisions handed off, not dollars saved. The payoff is how much sooner a CEO stops doing work that was never theirs to keep in the first place.
How do I know if a coach is the right fit before I hire one?
Glenn Gow asks every prospective CEO client to complete a self-assessment and a short round of peer feedback before he will take them on. If they resist that step, they are not ready for the deeper work CEO coaching requires.
Can a CEO use more than one kind of support at once?
Glenn Gow tells most of his CEO clients to build exactly that mix: a paid coach for structure, a board member or investor for immediate reality checks, and two or three peers for pattern-matching across companies at the same stage. None of those three relationships replaces the other two.
What You Do Next
If you just read Joshua Gould’s line about no one to call in the middle of the night and felt it in your stomach, that’s the signal. You don’t need another book on leadership. You need a coach, an investor, or a peer group in place before the next 3 AM problem hits. I’m Glenn Gow, The Scaling Executive Coach, and I built my practice around exactly this transition. Book a call with me and let’s figure out which kind of coaching actually matches where you sit right now.
