Your leadership style is holding your team back when the habits that built your company become the habits that cap it. Sam Jacobs, founder and CEO of Pavilion, leads a community of more than 10,000 go-to-market executives, and even he needed his own peer group to catch a blind spot he could not see. Glenn Gow, The Scaling Executive Coach, sees the same pattern in nearly every founder he works with.
Quick Answer
Your leadership style is holding your team back if you keep making every decision yourself, if your team has stopped bringing you hard truths, or if you feel more productive doing tactical work than leading. I’m Glenn Gow, and after 25 years as a CEO, 5 years as a VC, and more than 130 interviews with scaling executives on my podcast, I’ve found the same pattern every time: leaders rarely catch their own blind spots. They need a peer group, a 360 survey, or a mentor to name it for them first. The CEOs who scale past this point are the ones who install a mechanism to force that outside confrontation before it costs them a quarter of growth.
The Comfort Zone Is Where Leadership Goes to Die
CEOs retreat to what feels safe. Kim Hansen, CEO of Cake Equity, spent eight to ten hours a day coding on his own platform long after the company needed him doing something else. “I feel productive programming. I can see things coming out of my hands,” he said. “But ultimately, I was letting the team down on important business things and finances things and decisions that needed to be made.”
It took a direct order to move him. “I had an advisor that I really trust and really like,” Kim said. “He finally told me, stop coding now. And I needed to hear that so strongly and clear to make that shift.”
Chris Rolls, CEO of the Americas at TTC Global, hit the same wall moving from a technical consulting role into managing sales, marketing, and finance teams he had never worked in before. “Most people I see who are CEOs, who are ambitious, who want to grow, they also kind of think they’re Superman or Superwoman,” Chris said. “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.”
Every One of Them Needed Someone Else to Hold Up the Mirror
None of the leaders who broke through their limits identified the problem alone. Every single one needed someone else, a peer, a mentor, or an anonymous survey, to name the blind spot for them.
Levi King, CEO and Chairman of Nav, ran an anonymous 360-degree survey of his 100-plus employees during a leadership dispute with his co-founder. He rated his own communication a 9 out of 10. “I get it back in a hundred people say you’re a two,” Levi said. “For you to be a two, a lot of people had to say one, right? And so I had one of those moments where I’m like, they’re all idiots. That’s why I’m in charge of this company and they’re working for me. And I stood on it for a week or so.”
Sam Jacobs got his correction from a different mechanism. During a retreat with his CEO peer group, members wrote their biggest concern about his business on sticky notes. “Everybody pointed to me and said, you’ve got to fix the talent quality in your organization,” Sam said. He had been protecting an executive team the company had already outgrown.
Bryan Murphy, CEO of Smartling, learned this three weeks after eBay acquired his startup. eBay’s head of HR, a former Israeli tank commander, took him to lunch. “She said to me, ‘You know, you’ve got a lot of potential, but you’ve got a lot to learn,'” Bryan said, “and kind of sat me down and explained to me the things that I was messing up.” He was still operating on the force of will that built his first company.
Erik Berggren, CEO of Valhalla Capital, was managing an unfamiliar set of responsibilities during SuccessFactors’ hyper-growth phase, and his boss pulled him aside to push him past his hesitation. Erik recalls the moment: “What’s holding you back? Let’s go, like just go.”
Table: Two Ways CEOs Try to Catch Their Own Blind Spots
| Approach | What It Looks Like | Outcome for the CEO |
| Solo self-assessment | Reflecting privately, journaling, reviewing your own decisions without outside input | Blind spots stay hidden because you cannot rate yourself against information you don’t have |
| Structured outside confrontation | Anonymous 360 surveys, CEO peer groups, an executive coach, a mentor with permission to be blunt | Blind spots surface fast because someone with a different vantage point names them directly |
I built my coaching practice around the right column of that table. Self-review feels productive. It rarely produces the correction a scaling company actually needs.
The Nice Guy Problem
Carla Larin, CEO of Marxte, described the same trap from a different angle. “I must admit I’ve felt that way in the past that I’m the bottleneck to our company’s growth and the trajectory,” Carla said. “One is coaching for myself on, well, let me empower others to make decisions and I shouldn’t be the bottleneck.” Her instinct to stay close to every decision came from years of detailed spreadsheet and analytical work.
Sam Jacobs’ version of the same problem came from kindness rather than control. He kept an executive team in place out of loyalty even after the company outgrew them. Protecting people felt like the right thing to do. It cost him talent quality at the leadership level, and it took his peer group’s post-it notes to force the trade-off into the open.
Rajiv Parikh, CEO of Position 2, faced a version of this after two prior ventures that looked successful from the outside. “I felt like I could have been a much better CEO and a much better leader,” Rajiv said. “So I resolved as part of starting Position2 that I would be better whatever I was doing.” He didn’t wait for a crisis. He went looking for a Vistage peer group specifically to get the confrontation he knew he needed.
What Changes After the Mirror Shows Up
The leaders who scaled past this point didn’t just accept the feedback quietly. Levi King took his brutal 360 results and emailed the unedited version to his entire company, admitting he didn’t have all the answers. “Ruthless kind of self inquiry kind of keeps you in a good head space, keeps you humble,” Levi said, “and more than anything, it draws people closer to you because they can see that you’re trying your best to be the best version of yourself every day.”
Carla Larin’s shift showed up in how she talks about delegation now. “Not everyone should go through the CEO,” she said, describing how she now lets managers drive decisions forward without her involved in every step. Chris Rolls made the same shift after his company invested in a coach who ran a peer review of his leadership alongside a self-assessment. Chris said the peer review was “incredibly helpful” and led directly to “a personalized professional development plan.”
I named this pattern for my own coaching clients before I saw it repeated across dozens of my podcast guests: the CEO who scales is not the one with the fewest weaknesses. It’s the one who built a system to catch the weaknesses fast.
FAQ
What are the signs your leadership style is holding your team back?
Watch for a shift in your own motives, not just your workload. Sam Jacobs, founder and CEO of Pavilion, admitted he started “chasing some ideas about myself that I had let go of in chapter one, that I needed to be a certain status, that I needed to have a certain amount of wealth, that Pavilion was gonna be a certain kind of company, a big company, a billion dollar company.” Glenn Gow tells clients that when your goals shift from serving the business to serving your own image, your leadership style has already started working against your team.
How do you know if you’re the bottleneck holding back growth in your company?
You’re the bottleneck if managers routinely wait for your sign-off on decisions they’re capable of making themselves. Carla Larin, CEO of Marxte, spent years in detailed spreadsheet and analytical work before recognizing that instinct as the exact thing slowing her company’s trajectory. Glenn Gow tells clients that if you can name every decision your team made last week, you’re still the bottleneck.
What are the top 3 weaknesses of a leader that stall scaling?
The three patterns that show up most often are the comfort-zone retreat into tactical work, the Superman complex of trying to do everything personally, and a defensive reaction to feedback. Rajiv Parikh, CEO of Position 2, admitted he was “so good at debating that anytime somebody gave me something, I wanted to debate them,” a reflex that blocked him from hearing what his peers were actually telling him. Glenn Gow has found the defensive reflex is the hardest of the three to catch, because it looks like confidence from the inside.
How can a CEO tell if their leadership approach is holding them back from scaling?
Look for strategic drift: decisions that trade your original value proposition for a short-term revenue bump. Sam Jacobs described exactly this at Pavilion. “We chased growth and we chased revenue and we made a bunch of decisions that were bad for a membership organization,” he said. “It really was a period of strategic drift.” Glenn Gow tells clients that drift like this rarely announces itself. It shows up first as a series of decisions that each look reasonable on their own.
What are some signs that a leader has failed?
A leader has failed when their team stops surfacing problems until those problems are unavoidable, and when the leader hears about company-wide issues last instead of first. Sam Jacobs, CEO of Pavilion and author of Kind Folks Finish First, kept a struggling executive team in place out of personal loyalty, a decision his own peer group had to name for him before he corrected it. Glenn Gow calls this the kindness trap: the desire to protect people quietly becomes a drag on the whole company.
Should the CEO always be the final decision-maker?
No. Chris Rolls, CEO of the Americas at TTC Global, describes the end goal as building a “leadership engine,” a company that keeps making good decisions whether or not he’s in the room. Glenn Gow tells clients that if you’re still the final decision-maker on operational calls your managers are equipped to make, you’ve capped your own growth rate.
How can a CEO learn to make decisions promptly without becoming the bottleneck?
Speed comes from admitting what you don’t know about the functions you’re now responsible for. Chris Rolls asked himself this directly when he first managed sales and finance teams: “How can you add value as a leader when you don’t know their core responsibility better than they do?” Glenn Gow points out that a CEO who is fast because they trust their functional experts scales; a CEO who is fast because they decide everything alone does not.
Do 360-degree feedback surveys actually work for CEOs?
They work when the CEO takes concrete action on the results instead of just acknowledging them. After his peer group named his talent gap, Sam Jacobs didn’t stop at agreeing with the feedback. He hired a President at Pavilion to run day-to-day operations so he could focus on where he adds the most value. Glenn Gow tells clients that the survey or peer session is only the diagnosis. The structural change afterward is what actually moves the company.
How do peer CEO groups help identify leadership blind spots?
Peer groups work because other CEOs recognize patterns you can’t see in yourself, and they have less incentive than your own employees to stay quiet about it. Rajiv Parikh, CEO of Position 2, joined a Vistage peer group specifically to get this kind of confrontation, and says the shift starts with listening: “Sometimes it’s just about listening and letting and understanding that those folks are really trying to help you, and sometimes even that criticism is really someone trying to take you to a better place, not just venting about their issues towards you.” Glenn Gow encourages every CEO he coaches to join or build a peer group specifically for this kind of unfiltered input.
What’s the fastest way to expose your own blind spots as a leader?
An anonymous, structured check works faster than private reflection, because private reflection runs into the same instinct every CEO fights. Levi King, CEO of Nav, names that instinct directly: “The human instinct is always to like look externally in moments and like in hard times and say like, they’re the problem. That’s the problem. I’m not the problem.” Glenn Gow tells clients that a structured outside mechanism, like a survey or a peer review, is the only thing that reliably overrides that instinct fast enough to matter.
What should a CEO do after receiving harsh feedback from their team?
Treat it as the start of a relationship, not a one-time correction. Bryan Murphy, CEO of Smartling, didn’t just absorb the tough feedback from eBay’s head of HR over a single lunch. He let her become an ongoing mentor after that first conversation. Glenn Gow tells clients that a hard conversation only helps if you keep the door open afterward instead of treating it as a one-time fix.
What You Do Next
If you’ve read this far and recognized your own leadership style in even one of these patterns, don’t wait for a crisis to force the confrontation. Set up time with Glenn Gow to talk through where your blind spot is likely hiding and build the mechanism, a peer group, a 360 survey, or direct coaching, that will surface it before it costs you another quarter.
