Most scaling companies do not stall because the market disappears or the product stops working. Progress slows for a different reason: the leadership team quietly stops moving in the same direction.
This month’s Advisory Insights series focuses on that problem — executive leadership misalignment in scaling businesses. Over the next three episodes, three experienced advisors share the patterns they see when leadership teams begin pulling toward different objectives, often without naming the problem directly.
From the inside, misalignment rarely looks dramatic. It usually shows up as friction. Meetings that produce little progress. Teams that appear busy but move slowly. Leaders who agree on the goal but resist the actions required to reach it.
As Jeff Holman observes in the episode:
“Most scaling companies don’t stall because the market dries up. They stall because the team quietly gets misaligned.”
The difficulty is that these signals often appear long before anyone identifies the underlying issue. A CEO senses something is off, but the organization cannot clearly articulate why.
This series explores how experienced operators recognize those patterns — and what they do once they see them.
Misalignment rarely begins with open conflict. More often, it emerges gradually as leadership teams pursue different interpretations of the same objective.
In one example Jeff shares, he joined a law firm during a deliberate career transition. The firm had expressed interest in expanding its intellectual property practice and building relationships with startup companies. On paper, everyone agreed with the direction.
The meetings happened. The conversations were productive. But progress never materialized.
Over time it became clear that the problem was not communication or resources. The firm’s culture simply did not support the kind of change required to pursue that market. Leadership supported the outcome but resisted the behavior necessary to reach it.
The result was predictable: the initiative stalled.
Jeff eventually moved on and built the practice he envisioned elsewhere. In retrospect, the experience illustrates a common pattern in scaling organizations — leadership teams agreeing in principle while quietly operating with different priorities.
Another example from Jeff’s legal work shows the same dynamic from a different angle.
A client entered a strategic partnership that appeared promising. The agreement contained ambiguities Jeff advised resolving before signing. Those ambiguities later contributed to a breakdown between the companies, eventually leading to litigation.
Later conversations revealed something troubling: the opposing attorney had a pattern of intentionally leaving strategic ambiguity in agreements. The goal was to close deals quickly and postpone hard conversations about alignment.
In practice, that approach buried misalignment instead of addressing it. The relationship eventually collapsed under the weight of the issues that had been left unresolved.
Misalignment can exist inside leadership teams, but it can also exist between founders, investors, partners, and boards. When those differences remain unspoken, they tend to surface later — usually when the stakes are highest.
This month’s Advisory Insights series examines executive leadership misalignment through three different lenses. Each advisor works directly with scaling CEOs and brings a distinct perspective on how alignment breaks down — and how leaders correct it.
Derek Fredrickson spent fifteen years as a COO and second-in-command inside scaling businesses. Today he leads a fractional COO firm working with founders at the multi-seven to eight-figure stage.
His work focuses on the structural relationship between founders and operators — particularly the tension between visionary CEOs and operational leaders responsible for execution.
Derek frames this dynamic with a simple model:
When that sequence is unclear, organizations experience one of the most common forms of misalignment in growing companies: ideas without execution, or execution disconnected from strategy.
His episode examines how CEOs design roles and systems that keep the organization moving in one direction as it grows.
Robert White built a human potential training company that expanded across Asia, reaching more than 700,000 leadership graduates and operating training centers across multiple countries.
After losing that business and rebuilding his career, he spent the last two decades advising growth companies on leadership alignment.
Robert begins with a question many leadership teams skip: aligned to what, exactly?
Many organizations assume alignment exists because a mission statement and core values have been written down. Robert’s experience suggests otherwise. Teams can recite those statements without actually owning the direction of the company.
His framework focuses on building genuine alignment around purpose, vision, and values — and confronting a difficult truth for many CEOs: alignment often requires enforcement, not encouragement.
Ral West brings the perspective of a founder who scaled and sold her own company.
Over forty-five years, she and her husband built a travel business connecting Alaska and Hawaii. What began as packaging condominium rentals eventually became a scheduled charter airline operation purchasing wide-body aircraft capacity and selling tickets directly to travelers.
The company ultimately sold to Alaska Airlines.
Today Ral works with entrepreneurs and focuses on the cultural conditions that produce real alignment inside growing companies.
One practice she highlights is open-book management — sharing financial information with employees and teaching them how to read a profit-and-loss statement. The goal is to move employees from observers of the business to participants in its success.
Her episode also addresses a difficult leadership habit: how long founders delay addressing team members who are not aligned with the direction of the company.
Although each advisor approaches the issue differently, a common pattern appears across their conversations.
Leadership misalignment rarely begins with a dramatic moment. It starts quietly.
A founder works harder but sees less progress. A team executes well but in slightly different directions. A new hire looks strong on paper but never integrates into the organization.
Those signals often appear long before the leadership team names the underlying issue.
Derek Fredrickson examines the structural dimension of alignment between founders and operators.
Robert White addresses the values dimension of leadership alignment.
Ral West focuses on the cultural conditions that allow teams to genuinely commit to the direction of the business.
Together, they offer a practical picture of how alignment is built — and how it breaks down.
Before moving into the three advisor episodes, Jeff offers a simple challenge for CEOs listening to this series.
Many leaders can identify a moment when they sensed misalignment before the issue became visible across the organization.
The team member who appeared disengaged.
The project that stalled repeatedly.
The meeting that ended without real resolution.
Naming those signals is often the first step in diagnosing the problem.
Another option is to ask a direct question inside the leadership team:
Are we aligned on where this company is going — and does everyone here actually own that direction?
The goal is not to resolve every issue immediately. The goal is to understand whether alignment truly exists inside the leadership group.
A third option is structural. A CEO can step back and write down what the business should look like twelve months from now if everything is working properly. Then compare that picture to the current team structure and leadership roles.
The gap between those two views often reveals where alignment has already begun to slip.
Over the next three episodes, Derek Fredrickson, Robert White, and Ral West examine leadership misalignment from structural, cultural, and values-based perspectives.
For CEOs building scaling companies, these conversations address a problem that often hides in plain sight. Teams can work hard and still move slowly when leadership priorities diverge.
Understanding how experienced advisors identify those signals — and how they help CEOs correct them — is the focus of this month’s Advisory Insights series.
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
Transcript Segment Summary
00:20 — Advisory insights series introduction
01:05 — Why scaling companies stall
02:40 — Signals of leadership misalignment
03:20 — Law firm misalignment story
05:05 — Client partnership misalignment case
07:30 — Advisor series preview
08:00 — Derek Fredrickson episode preview
09:50 — Robert White episode preview
12:00 — Ral West episode preview
13:20 — Connecting the three perspectives
14:10 — CEO action steps to diagnose alignment
17:45 — Subscribe and episode close
FULL TRANSCRIPT
Jeff Holman, Host (00:20.428)
Welcome back everybody to the breakout CEO podcast. I'm your host, course, Jeff Holman. Really glad to be here with you today. You'll notice I don't have a guest with me. Today is going to be a little bit different. It's going to be a shorter episode because I want to introduce something new that we're doing. Every month we're going to have our advisory insights episodes. It's just a week with three or four advisors, people who work with scaling CEOs and founders and what types of perspectives and insights that they share with
their clients, those CEOs who are building businesses and the founders who are building teams, they share their insights and their perspectives with us on a topic. And so the topic this month is finding and fixing executive leadership misalignment in scaling businesses. So if you've ever felt like your leadership team is rowing really hard, but the boat just keeps going in circles or backwards or some other way other than forwards, or maybe doesn't move at all.
then I think this month's advisory insights series is gonna be fun for you. Here's something that I've noticed, okay? Both in my business and my career and in other businesses that I've worked with as an attorney. And that is most scaling companies don't stall because the market dries up, right? They stall because the team loses misalignment. And this isn't necessarily something that happens in dramatic fashion. It's not necessarily a big blow up, although that...
could contribute, but they stall because people oftentimes just quietly get misaligned because they're focused on different objectives, different metrics, KPIs, whatever you want to call it. They're focused on something different and they forget to come back to the bigger picture. And sometimes this goes on quietly for a long time before anybody can ever even put their finger on it. So this type of misalignment shows up in ways that might feel unrelated at first.
Right? You find that you're spending 60 or 70 % of your time on people problems, for example, or you're doing things that should be simple, but they're taking forever. You're just not getting to completion. Maybe your team is really busy, like I mentioned before, but your progress feels really slow. Or you just, sometimes you just sense that something's off, right? But you can't quite put your finger on it. You can't quite name what that is. Well, these are the types of things that often are signals.
Jeff Holman, Host (02:41.736)
of misalignment from the inside. It's not necessarily a blow up, like I said, just some type of friction that's happening in the business that you feel like it shouldn't be there. So we're gonna talk about this theme with our advisors, and I wanna introduce each one of them to you. Now I've got a story that I was gonna share about me going to a law firm and going to help start a, you know, I was gonna bring my IP expertise and help start an IP practice.
for that office. And at the same time, we were gonna also start more of a startup advisory division within their firm. Well, long story short, I went there, I brought my IP expertise, I had a lot of good meetings, at least I thought they were good meetings, they were meetings, I had a lot of meetings with partners and marketing and things like that about starting up this startup division. Because I wanted to actually take my career from
being what was really a strict patent practice for 15 years into more of a general counsel role like I am today. Well, we had a lot of meetings, but we just didn't have a lot of action. And I realized that we were just simply misaligned. Something in that business, and there were a lot of things in that business, but something in that business was just structurally not accommodating for even what they had agreed that they wanted to have in the business. So we couldn't accomplish it. Long story short, I moved on.
And you know, I'm doing now today what I had intended to do in that law firm a long time ago. I sometimes wonder if they had, if they had, if they realized what I'm doing now is what we could have been doing there in their firm, if they have any regrets about that not working. you know, so be it. That's where things came out. And I'm extremely happy with what the practice looks like today that I'm doing. I also had another story, and I don't want to go into too many details. Of course, I won't disclose anything confidential, but.
I had a client who entered into a business transaction with a strategic partner and they were, they, they intended, they talked and both parties said, yeah, this will be great. You know, you bring product, we bring, we bring the, the distribution expertise and it's going to be a match made in heaven. Well, come to find out after, you know, a lot of things went wrong. We were dealing with somebody on the other side who was in a legal function on their team.
Jeff Holman, Host (05:07.913)
And he, for whatever reason, he had this idea that you always want to kind of create these ambiguities and leave yourself out so you don't actually have to perform the things that you committed to perform, which baffles me because without performing those things, there was no reason to have the relationship exist in the first place. So, long story short, he sabotaged the deal. Now, I didn't know this. I had some suspicions.
You know, I'd warn my client upfront, hey, these ambiguities in these, in these deal documents do not make sense. Like we need to nail them down. You already nailed them down in the conversation. It doesn't compute why they are not, why they're not clearly stated the same way in the documents. mean, it was a, that's actually a red flag. Well, the, the client signed the documents anyways, and you know, long story short, they ended up having to separate or I think they might maybe still trying to separate. Who knows? It's been a long, a long.
process for all of them and for the banks involved and instead of actually having productive relationship, I think the idea was just, you know, how do we get out of this with the least damage to everybody? So big problems. In fact, I talked to somebody afterwards about that, somebody who was inside on the other party, right? He wasn't part of the deal discussions directly with me ever, but we met later and.
unrelated to this and the topic just came up. He's like, hey, you worked on that deal, right? He said, yeah, we always thought it was weird that our attorney wanted to do this type of approach with not just your deal, but every deal we did. okay. So this was intentional. was, he was literally, he thought, I think he thought he was being, I don't know, a savvy attorney or something, but what he did was just undermine that whole thing. Now that's not, you know, that's not a story of partners coming together or, you know, an executive leadership team.
Well, I don't know. I don't know if he was on their executive leadership team or not in that capacity. But clearly there was misalignment between the parties, right? The same way that there could be misalignment between founders, between your CEO and COO or CMO, between you and your investors. Like that misalignment can show up in a lot of different places and in a lot of different ways. So the advisors that we're talking to in the next couple episodes are going to help us navigate some of these things, right? And I've got three of them.
Jeff Holman, Host (07:32.623)
I've got Derek, I've got Robert, and I've got Raoul. They've all come to help share some insights and perspectives that I think you're gonna find valuable. So let me tell you about each of them and just give you a preview of those episodes that'll be coming out in the next days. One episode per day, I think you're gonna enjoy it. So Derek Fredrickson has spent 15 years as a COO and a second in command for scaling businesses. And now he leads a fractional COO firm.
that works with founders in the multi seven to eight figure level, right? So serious businesses, maybe the size of business that you are right now. His whole model is built around one idea and that is getting people in the right roles, which oftentimes means removing the founder from the day to day so that the business can actually grow, right? He's joining us from Paris, which I found was fun. I was there last year, I love Paris. And he and his wife had actually,
relocated there for quality of life issues, which I think maybe parallels what a lot of founders and CEOs are trying to achieve eventually. Now they're going to probably work really hard to get there, but in one form or another, a lot of our audience is working for ultimately quality of life. So Derek's episode is for anyone who's ever thought to themselves, I have a million ideas and nobody even wants to finish them. Like I can't get people to actually work on them. You know, that's a
Common problem for a very visionary CEO. Well, he breaks down why founders and operators are literally wired differently and why that gap when it's not bridged intentionally is one of the most common sources of misalignment in a scaling company. He's got a framework that I actually love, right? He said, it up, make it real, make it recur. So to put that into perspective here, the CEO is usually the one making it up.
the COO or someone in that operational role is usually the one making it real. And then hopefully if you've designed the system correctly overall, then the team can make it recur. Pretty simple concept, but it changes how you think about perhaps every hire and every handoff in your business. Our second guest is Robert White. He has a pretty interesting business journey that he shared with us. He built a human potential training company.
Jeff Holman, Host (09:54.314)
into it was one of the largest companies of its kind in Asia with 240 employees, 15 training centers across seven different countries. And apparently they trained over 700,000 leadership graduates. Pretty amazing. Then like some founders do, he lost it all. And of course, like founders do, he went back to rebuild. And so he spent the last 20 years now working with small and mid-sized growth companies.
on leadership issues. And he brings both the wins and of course the failures to that work. Well, Robert's episode gets at the root of misalignment. And he starts by asking a question that most leaders will skip, right? What exactly are we aligning to? So he challenges the idea that most companies treat alignment as a surface level exercise. Like we have a mission statement, we have core values, we put these on the wall or on a mug or somewhere, you know, we chant them at our.
team meetings perhaps. Well, his framework really is about getting your team genuinely to own the profits, excuse me.
Well, his framework is about getting your team to genuinely own the purpose, own the vision, the values of the organization, right? And he's direct about something that sometimes we avoid. And from his perspective, he says, alignment has to be enforced. It's not just something that we encourage, we've got to enforce it with our team. So his episode will make you ask yourself whether your team is truly aligned or maybe just politely compliant with each other.
Our third guest is Raul West. She also has a very interesting backstory as a founder and CEO for 45 years before turning to coaching other scaling CEOs. She, Raul, was a 45 year serial entrepreneur who, with her husband, built a travel business from nothing. And you think travel business, you know, what is that? Well, they used to, they lived in Alaska. They would travel to Hawaii, kinda split their time.
Jeff Holman, Host (12:01.089)
And they thought, other Alaskans will want to do this too. So they started packaging condo rentals together, right? And then they eventually chartered wide body jets and they were running what would be called a scheduled charter airline. Essentially buying out jet capacity, selling tickets and running their own travel service between Alaska and Hawaii. So they eventually sold that to Alaska Airlines and now she's coaching, like I mentioned, other entrepreneurs.
Rao brings in some of the really hard-earned perspective because she's been down this path and you don't get that unless you've scaled your own business. So Rao's episode is about culture as the foundation for alignment and what it really takes to get a team genuinely bought in, not just going through the motions, right? She talks about something that she called open book management.
Jeff Holman, Host (12:56.695)
She talked about something that she called open book management. This is actually sharing the financials with your team and maybe even teaching your team how to read a profit and loss statement, right? Turning your team effectively into real partners in the business's success. So she also has a lot to say about leadership courage, specifically how long a lot of founders will wait before they'll address a problem head on and what that type of delay can really cost the business. And then she's got one fruit.
Fruit Bowl analogy that I think you'll find interesting. So what I found across all three of these conversations with Derek and Robert and Raul is that misalignment rarely, like I mentioned before, announces itself with a huge, big, dramatic blow up or moment like that. It's usually something quieter that just begins slowly and then starts to fester. It's when a founder who's, like I mentioned before, these types of signals, when a founder is working hard, but not really not making progress,
or the team is executing, but they're not quite doing things in the same direction, or you hire somebody who looks great on paper, but they can never quite get up to speed or fit in with the team, all just different signals of misalignment. And so I think Derek's gonna give you the structural lens with roles and systems, kind of the COO slash CEO dynamic, whereas Robert's gonna give you the values lens, right?
Are you really aligned to something? What exactly are you aligned to as a team? Not just what have you stated are your mission and core values, for example. And then Raoul, she's gonna bring in another cultural and operational lens. How do you build a team that's genuinely in the game with you, not just employed by you? So together, I think it'll give you a pretty complete picture of what we're talking about. Now, before I hand you off to the advisory insights episodes with these guests,
I wanna leave you something perhaps a little bit more concrete because I know that inaction is often the reason that we get into misalignment in the first place and so I wanna give you a few actions that you perhaps could think about taking even before or right after you listen to these episodes with our guests. So I'm gonna give you a couple different options here. You can pick your poison if you want to, which of these sounds the best for you. But here they are. So one option, every leader I've talked to about misalignment can make
Jeff Holman, Host (15:20.877)
can name a signal that they saw and ignored, right, before the misalignment actually came to light. We've talked about what those signals might be. What I want you to do is go and think, just spend 30 minutes thinking about what types of signals for misalignment have you perhaps seen in your business already. Go write it down. Just put a name to it, but know, articulate what that is, and that can be your action. If you don't want to do that, if you don't want to sit down and name one of the signals in your business that might be
leading to misalignment, then here's a second suggestion. Go get your leadership team in a room or on a call, go talk to them and ask them, are we aligned on where we're going? And does everyone here actually own it? So don't just ask them if they know the mission statement or the core values, ask them if they own alignment on the executive team. And you might be surprised at the range of answers that you get, right? The goal isn't with this to go fix everything. It's not like,
Don't debate them on whether or not alignment exists. Just ask them if they, how much they own the executive team alignment themselves. So the goal is just to find out where the gaps are at this point, right? Now, those are two options. A third, it relates more to what Derek said. If you're sensing some structural misalignment roles that aren't really clear or accountability that doesn't ever quite pan out, then you spend 30 minutes.
this week, write down where you want the business to be in 12 months. So we're not necessarily talking about all the problems in the business, we're talking about what would it look like in 12 months if we have alignment. Now this isn't a business plan, you're not writing step by step how to get there, just what would it look like if we're really working in alignment in 12 months from now. And then of course once you have that vision, the second half of this is to ask yourself,
does my current team look like what I want to see in 12 months from now? And you can start to identify the perhaps what's already working and where some of the gaps are with your existing team. So that's it. There's three options there. If you want to do one of those three or if maybe you have another favorite that you want to do, but spend a little bit of time and think about where the misalignment might sit in your business. And I think if you do that once and then you listen to the episodes with Derek and Robert,
Jeff Holman, Host (17:47.947)
and Rao, it's gonna be a really productive time for you. Now, that's all I have for the episode for this little intro to our advisory insights series that's gonna happen this week. Two other things though, just as a podcaster, if you're not already subscribed to the Breakout CEO podcast, now's a great time, right? These three advisory insights episodes are gonna drop over the next three days and each one's gonna go a little bit deeper into the topic that we mentioned. I just don't want you to miss them and love to have you be a part of our community long-term. So go.
Go to your favorite podcasting platform, subscribe to the podcast and make sure you don't miss these episodes coming up. Second, if something today in the episode that I've talked about hits home with you, you recognize a pattern or something kind of lights you up about what you've heard, I'd love to hear about it. So go to LinkedIn, let's connect if we're not connected or if we are, send me a DM, send me a message, shoot an email to our team. Let us know what you thought about this episode.
Anyway, I'm really excited for what you're about to experience with the advisory insights episode. So thanks again for being here with me today and I'll see you shortly on the next episode.
