Why "Letting Go" Could Be Your Best Growth Strategy | Cary Prejean | 664
24 Aug 2025 · 31 min
Carey Prejean argues entrepreneurs become bottlenecks by refusing to delegate. She explains why the skills that build a company (vision, risk-taking) conflict with managing it (process, patience), and how to evolve into a leader who empowers employees and builds repeatable systems instead.
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Peter Winick. How do you help entrepreneurs stop being the bottleneck in their own business? In the world of entrepreneurship, people talk about working on the business rather than in the business, but the field of thought leadership makes this challenge far more complicated. Your book that you put out in the market might be available for $20 or $30. But your fee for an in-person workshop, a keynote, or an on-site could be 1,000 times more expensive than your book. Many thought leaders on the run are their own product. They sell their presence and their time. Worse yet, they serve as their own research and development team, sales team, and accounts receivable. They do a bit of everything. So how do you work on the business as your own CEO when you're wearing so many hats in the business. Carey Prejean, founder of Strategic Business Advisors and author of 3 books, has spent 40 years helping business owners evolve from operator to visionary leader. In this episode, we explore why great entrepreneurs don't need to become great managers. We look at how to build processes that run the business Without You, and why leadership, not micromanagement, is the key to scaling. I'm Bill Sherman, and you're listening to Leveraging Thought Leadership. Ready? Let's begin. Welcome to the show, Kerry.
Hey, thanks for having me, Bill. Glad to be here.
So I have an interest in origin stories, specifically how people get into thought leadership. Kerry, how did you get into this?
Well, it's actually became like a necessity in terms of working with business owners in terms of, I don't want to go on too long here, but most entrepreneurs are not good managers because skill sets are opposite. I mean, good manager, the skill set to be a really good manager is the opposite of the skill set it takes to be a great entrepreneur. So entrepreneurs, I don't want them to try and become good managers because it's good. They're never going to be really that good at it, but what they can be, what they're good at is becoming leaders. That lead their company to the next level. Right? So this whole thing about what is it to be a leader, they're asking the question, what is a leader? What are some things you see when somebody's a leader? You know, they have followers, they have a vision that's bigger than them. So it was all about having to work with business owners and showing them you need to become the leader that leads your company into the future. That's the next level, rather than you're going to try and manage it to the next level, which you're probably not going to do. So it became a necessary thing that I learned more about so that I could speak about it so that I could have some distinctions to show business owners like, this is, these are the things you need to do to take your business to the next level.
So if I hear correctly, some of that's making the invisible visible. You might've had a bunch of entrepreneurs who say, hey, I'm an entrepreneur. That's their identity. They want to grow the business. They want to scale it. Maybe they want to exit. And they know things are getting harder, but they don't know. And it's like, well, maybe I need management processes, but I was really a lousy employee for someone else, and that's why I'm an entrepreneur. And you're like, no, no, no, no, don't try to become the manager. Right, right. Yeah.
I mean, you know, think about what entrepreneurs want. They, they like— they're very dominant. They want their way because they see things as like, I'm gonna get that. They take action, they kick ass, they make things happen. Whereas a good manager wants, you know, I want to maintain the status quo, want to produce consistent results. Yes, it's going to be boring. It's going to be methodical. It's just pumping it out, pumping it out. Entrepreneurs, like, where's the next shiny object? Oh yeah, and that's possible. And it's possible. You got to chain them down sometimes and channel their energy into like 2, maybe 3 possibilities at one time rather than chasing 15 or 20. Entrepreneurs are impatient. I mean, they're extraordinarily impatient. Good managers are very patient. Again, entrepreneurs are more independent, whereas good managers are more on the team player type. Entrepreneurs like fast pace. Good managers want a nice steady pace. Entrepreneurs are very, I'll make it up as I go. Don't give me a lot of rules. Whereas managers, they want a lot of strict guidelines, rules, processes. This is how we do things. So the skill sets are like opposite.
Yeah. Yeah. And I want to sort of dig deeper. You said you've gone into thought leadership out of necessity, right? And I want to ask, how do you get the attention of someone who fits that entrepreneur profile, right? Because to get them to think of— they have to shift from entrepreneur to leader. They first got to be paying attention to you long enough rather than chasing the next shiny object. But how have you tried to do that?
Well, again, you can't get all of them to pay attention, you know, the ones that want to pay attention, usually they've hit some ceiling, they can't take it any further. And generally those are the ones who've grown their business to the extent that they can handle it personally, right? They're involved in it every day. They're in the weeds. They're having to save everything every day. And they're so bogged down with it. They can't do the things that make them great, which is like discovering possibilities and running possibilities, turning into revenue, building strong relationships, they're enmeshed in the day-to-day minutia of the business. And they're stuck with, okay, so how do I grow the business? We're stymied here. We've been stuck here for some years. We plateaued. Okay. So the way out is still be a great entrepreneur, but go one level better than entrepreneur, become the entrepreneur leader. In other words, leader is not different than entrepreneur. Leader is the next The next step, I guess, in being an entrepreneur. Listen, leaders are great visionaries. And what are entrepreneurs? They're great visionaries, right? So there's a lot of qualities in being an entrepreneur that translates into being a good leader, except good leaders are more patient. Also more, they're more willing to share the credit and let everybody do their thing rather than insist on my way. So that's, that's the big transition from entrepreneur to leader is you need to need some of those qualities.
That makes a lot of sense. So you've probably had to polish how you get an entrepreneur's attention because you've got a short window of attention before they'll go chase the next thing. How do you get them to go, wait a minute, tell me more. I need to know about that. I haven't thought about it that way. How do you shape the method?
Well, that gets back into Thinking versus just having thoughts, right? So we always have all these thoughts. We have all these thoughts going on and on. We have the snatter that tells us what's going on every second of the day. So the way to interrupt just having thoughts is to ask a question, because asking a question generally makes you think, okay, what don't I see here? What is the answer? Not this, I'm not talking about like, wrote, like what's 10 plus 10, but what is it about your business that has you, what do you think is Why are you stuck there? What's preventing you from moving forward? What's preventing you from growing your business? And a lot of times the answer is, I don't know. I don't know.
Okay. And how do you respond to, I don't know, because you've asked an open-ended question and I don't know is almost as much of a wall as you go as a no, right?
So you go through a series of like things that are missing, like, oh, you're missing a marketing plan. How's your marketing plan? Oh, marketing plan's great. Are you salespeople? They trained up? Yeah. How's your product? And then you start to find out what happens in the— in going through these questions, you start to find out, well, we don't really have processes. And yeah, we have a lot of breakdowns. And yeah, we've had some problems with customer service and getting things shipped on time. And yeah, we have some contentious, contentious bits of the business that are always fighting with each other. And yeah, I've had people quit because, you know, I blow up and they leave. And things like that. And it, oh yeah, I'm working 80 to 100 hours a week. I can't take any time off. You know, I have to rescue everything. So getting them to start to see all that is like, okay, then you start to explain, okay, so you're an entrepreneur and you start identifying the traits of an entrepreneur. Yeah, that's me. Yeah, that's me. That's me. Here's the traits of a good manager. Oh yeah, I don't really do that well, do I? Yeah. Oh, okay. Oh yeah. I have to be patient. I have to. Don't want repeatable results, how boring. But so it's getting them and asking questions to begin to think and see what's there. Not that they couldn't see it before, but they didn't have the distinctions to see it. Does that make sense?
It does. And so some of it is giving a language and a framework, and some of it is also giving them space to give an answer that's deeper than the quick answer of, of course we got a marketing plan.
Right. Yeah.
Yeah.
It's like, okay, so, so you start asking questions and they start getting to be honest. It's like, okay, so not every business is perfect. So you set up that contact. Not every business is perfect. Tell me what's not working. What are your, what are the chronic headaches that you deal with on a day-to-day basis? What are the problems that you've tried to address that don't seem to go away? All of a sudden they start, yeah, we got this, you know, this part of the business is a real pain in my ass. And I've tried to fix it. I've tried to fix it. I've tried to fix it. Okay. How'd you try to fix it? Well, I had a meeting. I said, this is the problem. This is how I'm going to solve it. And 6 months later, we have the same meeting again, rather than did you ask any of your employees their input was what they see, what solutions? Well, no, I mean, it's my company. I owned it. I started it. I'm the best person to manage it. Right? Are you? Based on results, based on what you're seeing, would you say you're the best manager for the business?
Would you hire you to operate the company? Yeah.
Would you hire you? Based on the results you're producing right now, would you hire you to come in and manage their company?
Well, and I think there's a very, really interesting crossover, which is one of the areas I want to get into, is that the spirit, and you use the word visionary, of someone who sees something different in possibility of what could be either in their geography or a new business idea or something. The entrepreneur is willing to take a risk to get there. The same is true with someone who practices thought leadership. They see the world as it might be, as it could be. They could say there's an easier way in negotiations or for innovation or for whatever their insight is, but they're also visionaries. Yeah. And what makes a good visionary isn't necessarily what makes a good CEO, whether in thought leadership or as an entrepreneur.
Well, it depends on what level of business you're talking about. And really, really big businesses, the CEOs of the C-suite, the whole management structure is really there to just maintain things.
Right.
And yeah, you want some growth, but it's in the small to medium-sized companies where the entrepreneur is still in charge. They very much want growth. So being a visionary is much more critical. Then, as opposed to something that's— well, you know, you have these global megacorps. Now, for them to achieve even, say, 10% growth, you're talking billions of dollars. But if they want to maintain, say, a nice 5 to 8% growth rate, I don't know, somewhere in there, and so there's some things to do, but it's like we have things too good, we're too established, let's not rock the boat, let's not take any crazy risk. Whereas when you're a small to medium-sized business owner, yeah, you want to take more risk. That makes sense.
And you're willing to rock the boat. You want to make change. You're willing to— And I think that's true, Volta, across thought leadership and entrepreneurship.
Right. You're willing to disrupt the status quo.
And with that, you may or may not have corporate background. You may or may not have a business school education. You may or may not really have all of the leadership skills that you need to lead, to take it past that point of, like you said, that personal arm's reach capacity, and that you feel like you've gotta be touching every email, every document, every proposal that goes out, and you become the choke point.
Yeah. Yeah. That, that's one of the things I say. If, if your business can't operate without you for more than a day, You're the, you're the bottleneck.
And I've said something similar on the thought leadership side of, okay, if you are the speaker, the author, the talent, the consultant, whatever, you decide to take 6 months sabbatical, what happens to the business? Do leads still come in? Do clients get served or does everything come crashing down? And if it's the latter, you got a problem. Yeah.
Yeah. For most, probably I would say 98, 99% of businesses, they would crash. Crash and burn.
Yeah.
Yeah.
Because you haven't built the repeatable, scalable systems and you're at the center of it all. Yeah. Everyone relies on you. So this is where—
It's not so much everybody relies on you, you've trained them to rely on you. In fact, you've trained them to, you only take it so far and after that the boss is gonna have to step in 'cause you're not authorized. And don't get, don't get any crazy ideas out of the box and do anything, cuz you're not gonna do it the way the boss likes it or the way the boss would do it. He's gonna come in and slap your hand, not cuz you didn't do it, you didn't solve the problem because you didn't do it his way or her way.
And it could have been a little bit different this way, and you should have asked me, right?
Yeah.
Yeah.
That's one of the things I hear constantly. It's like, yeah, did something happen? I solved it. And the, instead of thanking me, what I got was, yeah, okay. Uh, that's not the way I do it.
So if you're enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you'd like to help spread the word about our podcast, please leave a 5-star review at ratethispodcast.com/LTL and share it with your friends. We're available on Apple Podcasts and on all major listening apps as well as thoughtleadershipleverage.com/podcast. Let's talk about your background and your expertise. You're advising entrepreneurs and you're working with them on leadership. Why is that a lane that you care about? What about it is exciting to you?
Well, my background, my training is in accounting, right? So when I first started, it was mostly about ratios, financial analysis, making recommendations for your— your business is profitable, but it's financially not that strong. So we need to do some things to strengthen the—
your cost of sales and your COGS. What's going on here? And explain to me this lease that you have on the building.
Yeah, right. Things like that. It was all financial. And what I, what I got was that most business owners don't know how to read their financial statements. They don't know what to do with actionable financial data. They know how to find possibilities in terms of revenue. And they don't, they don't have training for things like accounting, logistics, inventory management, HR, whatever. All the other stuff is, they've never been trained in that. They don't have any experience in that. So they fumble through. So The whole thing about over time, I evolved that I had to be something more than just a numbers guy for these guys to really take that business off. Right. I had to, I had to learn the distinctions of what it was to be more than just a business operator. That's what most business owners are. They're really not, they own the thing, but they're really more operators than owners. They can't step away and be a great owner. So it had to be some education I undertook. That allowed me to make some distinctions about leadership, about next level, about having a bigger game, having a vision that allowed me to talk with them. I have conversations that got them to see possibilities that they didn't see before.
So your initial conversations, let alone the follow-up conversations, changed. Those first questions that you would ask at the beginning went probably from things that would appear on a P&L or a balance sheet too, then how's it going? You know, what's your own issue?
You face it. What I get is like, here's all your financial stuff and here's some recommendations for it. You go, yeah, but you know what, that's going to be hard to do because we got this, you know, we got this issue over here that's preventing that. So, you know, it was not, it wasn't an accounting thing, it was an operational thing. So I was like, okay, well, what you going to do to solve that? Well, I don't know. We've been trying and I'm, I'm a financial guy. I don't know how to solve that. So one of the things I got really clear about is one of the things that makes the business operate well is to have real well-defined processes that everybody follows, everybody's aware of. They know their job, other people's jobs, and have the process run the business rather than the owner always getting there and mucking it up.
So let's stay on that question of the owner getting in there and mucking it up. To quote you. How do you help them let go?
Again, it's about building processes that work. And what you want from the owner is not, I don't want you to, I don't want you to have really anything to do with the process other than what I'm looking for from the owner is what are the consistent results you want to see this process produce? And again, the process has to be about a critical function of the business. Sales, accounting, cash flow, whatever. All that. So there are processes in place to handle these functions. But first, tell me what results you want to produce, and then it's up to the employees that actually do that thing. We'll all participate in there. They come up with a process because they see things at a more granular level. The owner's gonna miss some of the really finite, minute things about it that make the process actually work well. I mean, that's why they have the thing, you know, here's a problem, here's a solution, and 6 months later you're having the same meeting about here's a problem, here's a solution.
Right.
So when the, not only that, when the owner, the employees put a process together, they own it, especially when they get it to where it works. It's producing consistent results. Now they own that because now this is an easy way to get work done. There's not all this conflict. There's not all these breakdowns and you're delaying me and no, you're delaying me and you did wrong. Now the process is, this is how that flows and the owner steps back. So now that's one part of the business they can start to let go. So the more processes you build. The more they can let go, the more they can let go, the more they're gonna let go. 'Cause now they trust that the processes are running the business, produce the results that they want, rather than I gotta run around and make sure, save the day all the time. And again, even with that, they don't always get the results that they want.
So let me ask this question. I want to turn the question to you in terms of thought leadership. You've written books, you're doing thought leadership. Where do you see that work going? Do you see it increasing, decreasing? How are you getting value from the books that you've written?
Well, I'm going to keep doing what I've been doing, and I also— one of, one of the things I've been doing is continuing with my education. Like, what else is out there that I can help business owners with? What else is, what else is entering the, the business dynamics that business owners need to be aware of? And one of the One of the things that's really crucial right now is AI. You need to integrate as much AI as possible into your business, into your processes, because it increases productivity like crazy. So I've been building AI into my practice in terms of helping clients as well as processes that I use in my business. And again, it saves me tons of hours. I can't tell you how many, but that's something that a lot of business owners It's kind of foreign to them. I mean, it's kind of alluring. It's kind of sexy in that it's something new, new shiny object. But at the same time, it's not something you just look at, oh yeah, yeah, I got that. It's not that simple. You have to learn how, instead of coding, you have to learn how to prompt well. And that takes some thought. So how do I talk to this artificial intelligence in a way that it's going to give me the answers that I want? And how do I, and again, that takes practice, that takes refinement. And most business owners don't have the patience for it. So who in your organization, or several in your organization, who can we put in charge of or get trained in AI and prompting and how to use it for your business? Because the owner's not going to do it.
Well, and it's an interesting question if I circle back to the conversation of moving from entrepreneur to leader. Who's going to talk to the employees like a leader? How are you going to prompt them for the outputs that you want? There's a parallel there, right? In terms of what are you asking for and are you willing to let them figure out how they're going to do that? With AI, it's a black box. I don't know if anybody can tell you exactly based on the prompt, all the steps that are involved. But here on the human side, you also have to be able to say, this is what I'm looking for. This is what success looks like. You figure out how you're going to get there. I'll hold you accountable to the success.
Yeah. I mean, again, it's about these are the results I say I want to see. Okay. And if you have any parameters with that, like there's certain budgetary constraints or time constraints, whatever. I want to see these results in this amount of time, and I want you to spend less than X amount of dollars. And again, it may be that we can't do it within those constraints, you know, but you need to try and try really hard. We can do it in this time space or in this for these dollars. You know, you still want us to produce those results, but you have to give employees—
I can't give you better, faster, and cheaper. Which two do you want?
Yeah. And I see that there's a mechanic I go to and he has that in his garage. You can have, you can have fast and cheap, you can have good and fast, you can have, you have a combination, but you can't have good, fast, and cheap. Doesn't exist. So yeah, so you have to give, you have to give employees not only permission, but the support to do things on their own and to make mistakes. And not see mistakes so much as a mistake, like he screwed up, you're endangering my business, my income, my wealth, because that's how most business owners speak about my wealth. My revenue, my sales, my this, my everything. And so what's in it for the employees? Paycheck. Okay, well, what do I have to do? What's the minimum I have to do to just get my paycheck and not get fired? So you have to actually support them, encourage them, elevate them, and what I call empower them to do what it is you want them to do. And again, you have to enroll them in your mission. You have to enroll them in your vision. Like, okay, this is where we're headed. Here's what— here's your part of it that I see you contributing. What can you do? These results we want to produce, what can you do as a group? How can y'all put together a process that's going to produce that? Because that's really going to help the business. It's going to help you as employees. It's going to make your job easier. And as we're more profitable, you'll get more— you'll be able to get paid better.
Right. It's really hard to put up a sign in the break room that says, maximize shareholder value, or the owner needs a third yacht, you know, and expect morale to improve.
Yeah, yeah, exactly.
So as we begin to wrap up, Kerry, I want to ask you about books. You've written several books.
Yeah.
You were an accountant in practicing accounting. Did you ever see yourself writing a book or was this a surprise?
Early on? No, I know. And listen, the other thing, the books that I write for business owners, that's kind of great. I've had a few business owners, non-business owners read them. It was like, okay. And then, yeah, I'm not John Grisham. I'm not trying to write—
yeah, this is not a novel. I am speaking to a specific audience. Yeah. And you're not it.
I'm not, I'm not looking for Pulitzer Prizes or, you know, New York Times bestseller. This is business owners. It's a way for them to see themselves, the way the world sees them, as well as a way for them to see how they, how they sometimes, the way they act in their business is not empowering for them. It's not effective, it's ineffective, it's destructive actually sometimes. And how can you be different? How can you be a better entrepreneur leader that's going to have your people really want to rally around you and support you and join you in your mission, as well as some practical Here's some things you can do to increase your revenue, increase profitability.
What do you call it?
Empower, engage your employees, build a better business. And again, I'm not expecting them to do it on their own. They don't have the, they don't have the follow-through, they don't have the attention to detail. But if maybe you can find somebody in your organization, if you're willing to trust them enough, they can do it. Or call me or call somebody to come help you.
Do you see yourself writing more books or have you said what you need to say and they work for business development? You know, some people tell me they've got 12 books still inside of them. What is true for you?
Actually, I'm, I'm in the middle of writing 2 more. Okay. I was guessing there'll be more beyond that.
At the same time. That's a challenge. Yeah.
Well, one is about things not to do in business and I've seen some in the last few years, I've seen some really horrendous endings to businesses that were like institutions, just incredible the way they fell apart. And the other thing that's really missing a lot that I say is missing in business is the art of relating. We've gotten so sloppy at actually being able to relate one another and be effective in our communications, you know, where we're all usually kind of half-ass sloppy with it. And then we make sloppy requests, sloppy offers, sloppy promises.
I sent you a one-sentence email. Wasn't I clear?
Yeah. Well, you know, the thing I get from clients from, especially the entrepreneurs, they'll forward an email to me with nothing of their own. Just like, here, you're like, I'm supposed to read this, interpret it, and then take some action. So I usually respond back with—
Now, be clear what that action is, then infer what to do.
Yeah, yeah, definitely. Perfectly. So I usually respond to that with, is there a quest in this?
Exactly.
You're gonna have to, you're gonna have to talk to me. I, I don't reach through the ether and know what you're thinking.
Mm-hmm. Mm-hmm. So you've got two books coming. Okay. What's the strategy for them? Where, how are you gonna use them? And are you doing anything, will you do anything different with them than what you've done with your earlier books?
Not really. I mean, the one on how not to, or how to ruin your business, it's really just like a warning sign. If you see any of this going on in your business, be careful. I've seen some really strong businesses go up in smoke because they were headed down these paths and the owner or owners, they couldn't see the warning signs and they just went off a cliff. And The Art of Relating is hopefully something that owners can take, or whoever can take, in having more effective relationships, not only at work, but maybe in their personal lives, husbands and wives, parents and kids, you know, it's just, how do you relate to another person in a way that they're going to get it, that you care, that since that you want to take care of them, that you're clear in your communication, that you coordinate action better, that you're more effective, you know, because if you look at, if you look at any organization or business, it's really a, it can be boiled down into a network of conversations. That makes sense. The work, the production level people, they're more concerned with fulfilling promises, right? They come to work and do this work. The manager supervisor level, they're more concerned with requests, offers, and promises. They're trying to coordinate resources to produce consistent outcomes or maybe even better incomes. Whereas the C-suite people are more concerned with, uh, making assessments and declarations about the future, where the company's headed. They're not so concerned with fulfilling promises, right? Or they're not so concerned with— I mean, they do make requests often and promises, but their main function, the main thing they do is make declarations about where the company's headed, but they need to make good assessments in order to do that.
Well, and I like how you're splitting out the language in a very approachable way. And you can start saying, okay, am I making a declaration? Am I making a promise? Am I making an evaluation? It gives a framework of what role am I playing currently, right? And am I flying in formation, right? Am I doing what I need to be doing, or am I the CEO who's checking every promise?
Yeah, if you, if, if you're the CEO and you're going through what everybody does and you're micromanaging everybody, there's a reason you might be stymied. There's a reason you might have, you know, you've gotten stagnant.
We found the reason for the ceiling and it is you.
Yeah, the old Pogo cartoon, right?
Yeah, exactly. Exactly.
We have met the enemy and it's us. I forget exactly the line, but that was basically it.
I think that's it. I think that's it from the cartoon. So I want to thank you, Carey, for joining us today for a conversation around entrepreneurship, thought leadership, the evolution to leadership itself, and then realizing what role are you playing, how do you empower others, and get out of your own way.
Yeah, Bill, thanks for having me, man. It's been a great, great conversation.
Thank you, Kerry.
Absolutely.
Okay, you've made it to the end of the episode, and that means you're probably someone deeply interested in thought leadership. Want to learn even more? Here are 3 recommendations. First, check out the back catalog of our podcast episodes. There are a lot of great conversations with people at the top of their game in thought leadership, as well as just starting out. Second, subscribe to our newsletter that talks about the business of thought leadership. And finally, feel free to reach out to me. My day job is helping people with big insights take them to scale through the practice of thought leadership. Maybe you're looking for strategy, or maybe you want to polish up your ideas, or even create new products and offerings. I'd love to chat with you. Thanks for listening.
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