In this efficient episode, Scott Abbott, Founder and CEO of BOS-UP, shares how to lead executives effectively by blending robust systems with human-centered leadership, EQ, and intentional “Boss Up Moments” to scale beyond founder-driven chaos. If you struggle with executives falling out of alignment despite a strong team, or if you find that your drive and decisiveness now work against you at this level, you won’t want to miss it.
You will discover:
– What it truly means to lead from the heart while maintaining strong structure
– Why what got you here as a founder will now work against you as a CEO
– How to shift from managing people to building systems that create real alignment
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to The Start, Scale and Succeed Podcast, the only podcast that grows with you through all seven stages of your journey. As a founder, I’m your host, Scott Ritzheimer, and we’re talking for those of you in the CEO stage today, folks who have finally built that leadership team, that executive team around you, only to discover that leading executives is an entirely different game that nobody told you about, because they’re different they’re different creatures, and if you’re doing it, you know exactly what I mean. And the hard truth here is that leading those folks Well, their expectations and their needs and how to succeed at this stage requires a different set of skills, soft skills that got you here, that drive decisiveness, personal output, those are all good, but they’re not enough, and if you’re not careful, will actually work against you when it comes to leading others at this level to solve this problem.
We’re not going to try and do it alone. We’ve got our guest today, Scott Abbott, who’s the founder and CEO of the boss up coaching solution and Academy. He’s also an executive coach, angel investor, entrepreneur and best selling author with over 35 years. Over the last 35 years, sorry, Scott has built, brought and bought and scaled companies worldwide. I need to wear my glasses when I do these and he’s conducted more than 10,000 coaching sessions to help founders and teams strengthen their systems, alignment and performance. His latest best selling book, boss up moments, blends leadership, psychology and soft skills into a modern visual field guide for growth in business, work and life. Scott is known for his solution centric coaching and his passion for unifying business operating systems with AI and Human Development. He’s here with us today, Scott, welcome to the show. I’m glad to have you here. I’ve been looking forward to this conversation. We were delayed slightly, but we’re now together, so the anticipation is even greater. You’ve worked with a whole lot of executives, and you’ve built this entire framework around what you call boss up moments. And I’m wondering if you could just unpack that, what are these moments? Why do they matter so much, and how does success in this area start to expand beyond these particular moments?
Scott Abbott
Thanks and thanks for having me on the show, Scott, as the expression goes longtime listener, first time honor, I guess, to use an old radio term, if you remember that. So, so, yeah, I think you know the emphasis of boss up and moments, specifically, the book moments, is we don’t leap into failure or stumble into success. It’s stages and phases into your intro about CEOs and the difference between a CEO, a president, a founder, an operator, a visionary, a leader. While they’re all contextually in the same ballpark, they’re in different positions and require a different set of skills. And so for me, the boss up coaching solution Academy is really three parts. It’s a systemic way to help companies build, run, grow and scale and exit. Second, this little thing called AI automation technology.
And third, back to coaching and consulting and counseling. So we think it’s this blend of head and heart purpose and profit, passion and production and so with moments, what we really try to do is emphasize the human side, the EQ, the ability to contextualize and harmonize, in addition to the systems, and to your point, as you scale and grow. And you know this, you know what got you here is not going to get you there. And so between the boss up blue book and moments, it’s this, again, fusion of engineering mechanics, this practical way to build, run, grow and scale. And then we need these things called humans, starting with the founder, the CEO, and hopefully they’re going to be their best to lead and guide and manage. So that’s what it’s all about, and that’s what we’re just trying to emphasize, is, yeah, we love big picture and systems and infrastructure, but let’s make sure we appreciate us as humans and those around us in the moment, so we don’t find ourselves in bad places.
Scott Ritzheimer
Yeah, it’s so true. One of the things that’s interesting about that is, well, I think a distinct challenge of this stage is the level of complexity. It’s not enough to just have a coach, or to just build, run, grow, scale your business, or to just implement technology, right? One of the hardest things about this stage is that there are so many hard things to tackle all at once. And the reason why we have an executive team is because we can’t do all of that on our own. But the challenge that comes with that is we think it’s a little like, if you build it, they will be aligned, you know, if you get what I mean, but like, that’s a big mistake thinking that just because you hired them, just because you like them just because you’re sitting in the same meetings, that doesn’t necessarily mean that alignment is going to take care of itself. What is it that causes high performing executives that we think should be in alignment to actually fall out of alignment?
Scott Abbott
Well, I think one of the misnomers in the world, especially with a lot of let’s just call them entrepreneurs and founders. Have this, you know, almost romanticized perspective of grit and and hard work and to your to use your word likable as you grow and scale, and especially if you want to create enterprise value, both for a sales side exit or just a succession plan and pass it off to another generation, another person. You know, most founders keep a lot inside. They know what to do and how to do it, and they and they got from here to there based on that. Now it’s time to call what you will systemize. And you know, one of my favorite expressions to emphasize this is by isdore sharp, the founder of four seasons, and he’s quoted as saying, systemized, predictable, the humanized, the exceptional. And so you really want a 10x which is a concept, not a binary equation. You’ve got to figure out how to systemize. Let’s just call it what they are, the standard operating procedures. But it’s not only that you can actually embed values and standards and principles. I’m a big fan of the Indiana Hoosiers. I live in Indiana and do a lot of work with IU and obviously we know this little football team went from the losing his program to 16 and oh, and won the national championship. And if you listen to Kurt signetti, it’s around what we’re talking about. Yes, teamwork, but he always emphasizes production over potential.
He emphasizes systems and alignment. And when you do those things right, moment by moment, and you focus on that, not the results, I think that’s another thing that happens. Hey, they people tend to focus on the results or the outcomes or the achievements. Well, you don’t result in the results. You don’t achieve. And to achieve, you get there through ideally good systems, good alignment people knowing what their roles, accountabilities, responsibilities are, how to measure, how to manage. And for a lot of founders, man and early stage and entrepreneurs, that sounds kind of like corporate bureaucracy. Yuck. And this is what’s counterintuitive, the better systemization you have to everything we just talked about, you actually liberate yourself, Scott, you free yourself up to be a better mentor, coach, leader, visionary. And I just think that’s not only counterintuitive to a lot of founders, I also think it’s not necessarily what they want to do, right? But again, as you grow bigger, you realize it’s not about you, it’s about others. You become more of a servant leader. You become more even if you’re not public. You should think that way, right? You’ve got stakeholders and investors, even if you don’t technically, that’s the mindset you should have. And so we believe there’s five stages to a company. Once you get the stage three and above, you’ve really got to have better structure, infrastructure, systemization, otherwise, you really are kind of making about you, and it shouldn’t be about you as much as it used to be.
Scott Ritzheimer
That’s so true. It’s so true. It’s one of the big dividing lines between stage four and stage five in the founders evolution. So Scott, you struck a chord here that wasn’t planning on going down this route, but I think it’s really, really important, and it it ties a lot of the tension of this all into one thing, and that is, you talked about systematizing. You talked about adding SOPs. I think everyone’s heard that at this point. But here’s the mistake that I see folks still make, especially founder CEOs, is that they delegate all of that to somebody else and a better language, they abdicate from it themselves, right? And so here’s the problem with that. You might not be the best systems thinker in the world, and most founders aren’t right. It’s just okay. That’s normal. That’s not a problem. But if you don’t include yourself in that conversation, your systems will have values in them. Now the question is whether or not they’re your values. So talk to us more about embedding values. What does that look like? What does CEO involvement look like in building out these systems?
Scott Abbott
Well, you struck a chord with me, because there’s a lot of frameworks and quote, unquote systems that are out there, and I think ultimately, one a few of them are very popular. Because I actually think, if everybody’s being honest, they abdicated to it, and they start to follow an acronym or a term or a book title, and that’s, that’s not the way you’re supposed to do it. That’s, that’s lazy, that’s mediocre. But, you know, a lot of humans take that route, unfortunately. So, yeah, I think the embedded, the inclusive, the integrated, you know, it just reminds me of the classic, you know, it’s not personal. It’s business rubbish, right? It’s all personal because we’re humans. So the founders and leaders who find that line between delegate just to delegate and delegate to elevate both your team and yourself, which means I need to learn. I need to roll up my proverbial shirt sleeves and get my hands dirty. I need to know now look at AI. Do I need to know agentics 205, and do I need to be a coder? Absolutely. You need to be a strategist, you need to be intelligent, you need to be practical. But I don’t need to know what.
I don’t need to know you with me. And so again, ideally, everybody agrees to what we. Call rules based or agreement based commitments. That sounds more humane, and that includes, again, the day to day job and x’s and o’s and SOPs and the KPIs and OKRs, all those acronyms, right? But ideally, they also have an appreciation for X percent of their time is to improve themselves working on, not just working in, yeah, and if they basically embed that, I truly believe that today, Scott leadership, learning and development should almost be like a utility bill. It’s a uncheck the box, not check the box. And if you’re not spending five to 10% of a working week to invest in yourselves and those around you to be better as leaders, managers, team members, you’re missing the boat, especially because of what’s happened over AI and the changes in workforce. Okay,
Scott Ritzheimer
yeah.
Scott Abbott
So,
Scott Ritzheimer
yeah,
Scott Abbott
it can’t be a nice to have. It literally needs to be part of the system, if that makes sense. And so I just this concept of inclusion, of integration, of fusion, you know, over the four decades, I’ve been doing it, sometimes it’s been pushing wet noodles, and my dad says, You can lead a horse to water, you can’t make a drink. I do think there’s a better appreciation of the why, the how now and the who and the when. That’s a different story, but, but I do think, I do think we’ve gravitated to a more reasonable reality than when I started working. There was much more of that classic hierarchical, you know, do as I say, and this is my title, and I get away with bad behavior. I think a lot of that is changing for the good, but I still think it’s a challenge to figure out actually how to get it done.
Scott Ritzheimer
Yeah, I think a conversation that I hear outside the business world around AI, but not as much inside the the business world. And I think it’s a problem ties directly to this and and I think, as CEO of of an enterprise, especially if you’re pursuing some kind of whole, whole scale adoption of AI throughout your organization, is that it has to align as well, this idea that AI is automatically aligned with, you know, our Standard for customer service or our direction as an organization, I think, is not the case. And one of the things I don’t see happening in a lot of the AI conversations is, how do we make sure that the AI tools that we use and the way that they’re used is in alignment with who we are and where we’re going? Are you seeing something similar?
Scott Abbott
Well, I’m also having a little deja vu. I’m a little older than you, so I, I started my first company in 1995 as the joke goes, right after Al Gore invented the internet. Me and my friends at IBM created what is now basically the way commerce and communication gets done. Right? The internet’s the backbone to almost everything these days. So, so I was there in the advent of that. Then, speaking of IBM, I wrote a book and did a 28 city tour 18 months, about 15 years ago, when this other major wave came in mobile technology and the use of social media in the enterprise. And, you know, I have some PTSD at a lot of you know, memory that that was freaking people out big time. That’s why I wrote a book called the cofactor, and we talked about systems of engagement and a whole host of new concepts and criteria. So maybe I’m a little more, you know, positively pragmatic, having spent 40 years in tech, both on the delivery and on the acquisition side, that, you know, some good old fashioned things still need in place, right? We need governance. We need policy,
Scott Ritzheimer
yeah,
Scott Abbott
we need systemization. We need alignment, right? We need all the above to do it right at the same time. You know, we don’t know what we don’t know yet. And so back to again, good systems. Make sure you do the present and the future. Make sure you appreciate the hard and the soft. Make sure you appreciate the fiduciary and the governance with, again, culture, values, standards, as you said earlier, and now today, just like I believe learning and development should be embedded in your infrastructure, so should AI. If you’re on a leadership team, we call them roles, accountabilities, responsibilities, and if each one of your leaders and you does not have AI, and I’m not gonna tell you what to do with it, how to do it, et cetera, et cetera. But what I would say is it is absolutely an embedded imperative reality that you’ve got to figure out what and where and how it aligns. And it’s a journey. It’s gonna be a journey. It’s gonna be a long journey. I would just say again, AI, is, is, is, is is, ideally, for most of us, a strategy. It’s, it’s a way to provide a lot of great value, and absolutely, we also have to be careful not to do things that we shouldn’t do.
Scott Ritzheimer
Yeah, that’s so true. So true. I think if I were to sum up a big portion of this conversation, the advantage that founders have is that they’re the founder right and that these values are highly aligned with who they are. You have a good backbone and culture, but your job now as CEO is to make sure that that’s implemented in these strategies, to make sure that it’s pushed deep into these systems and. To me, I think that’s really the key to doing it without losing yourself, is recognizing those parts of you and actually embedding them, institutionalizing them in the organization. Would you agree?
Scott Abbott
Yeah, well, sorry for the plug, but you know, I’ve got a I’ve got one of our moments in here is called 1080, 10, and it’s not going to happen overnight. But here’s the concept, if you’ve got good systems, and you’ve got the right leadership team, and you’re following what we call the nine core competencies, and you’re embracing the essential concepts, tools and disciplines, that usually takes about a year to get in. But once you feel you’ve got a good foundation from a system, I believe founders, visionary CEOs, should follow what we call the 1080, 10, and it’s based off the Pareto Principle, right? The 8020 rule. We’ve all seen that, but ideally the 80% of the day to day, X’s and O’s, blocking and tackling, the delivery, the production, the servicing of the sales and marketing, that should be the system and your leadership team.
You with me? So the founder, the visionary, the CEO, is actually now spending 40% of their life in the first 10% of what companies deal with, and that’s marketing, innovation right being out in the world, doing market, business, sales development to generate new pipeline, new opportunities to think down the road, and then the other 40% of their jobs should be on the back end saying, Thank you, mentoring their people, coaching them up, getting back into the market, and say, you know, Would you like something else with that? You follow me? And again, a lot of people get caught up and think, Well, if I do that, I have to be a good coach or a mentor or be a better talker than I am. That’s not true. Back to again, systems and being authentic. We have a principle we believe in, called clear, and it’s a pursuit of clarity, but it’s also an acronym, collaborative, logical, empathetic, authentic and resilient. You notice I didn’t say anything about charisma or that you’ve got better bedside manner than the other people? Have? You follow me? So, yeah, I think the beauty today is Know thyself.
Ideally you’re still developing yourself, right? Because you ain’t growing, you’re dying, but don’t try to be something you’re not. And I think that’s the beauty of systemization, AI, when it’s done properly, right, and appreciation, what we call humanization. And so don’t try to BS anybody or be something you’re not. And I think leaders today, especially entrepreneurs, founders and visionaries, frankly, the only reason Scott why they can’t get from here to there, given our conversation, is themselves. And that happens a lot where people just can’t get out of their own darn way.
Scott Ritzheimer
Yeah. So true. Scott. There’s another question I have for you, and then I want to make sure folks know how they can get a copy of the book and find out more about the work that you all do. But the question before we get there is this, what is the biggest secret you wish wasn’t a secret at all? What’s that one thing you wish everybody watching or listening today knew?
Scott Abbott
I think I’ve said it. And, you know, they say repetition, redundancy is the mother of learning. So I’m a pretty redundant, repetitive guy guilty by by choice systemization. Scott, and again, I know in this world today, systems get a lot of guff, but let’s be clear, systems don’t make bad systems people do. And just look around your life and your world and think about the good things that happen thanks to systems from the streets to the to the skies to the bridges to your life. Just think how chaotic it would be if we’re all just making it up and following Nike’s advice to just do it. Yeah, so I think counterintuitive, and it took me a long time. My dad’s a mechanical engineer. I was an entrepreneur at young age. I love my dad. He’s my hero, but I think he pushed my buttons. I moved around a lot, so I kind of fancied myself to be this entrepreneur that adapted and adopted and I see all this, especially tech MVP and agile. And yeah, I get the concept.
But believe it or not, counterintuitive is this, the more better systemized you are, the more it actually liberates you, Scott, to be what you want to be and who you want to be. And that’s, that’s something that, if I learned it earlier, I probably wouldn’t be with you today. I might be, you know, hanging out on a mountaintop somewhere, you know, my own chalet. Good news is that didn’t happen. But, yeah, I would say it’s just what I just said, the power of good systems, the fusion of, again, the right technology and automation. Harnessing the concept of coaching and being coached, certainly it’s central to boss up. So sorry for that candor, but that’s our passion. Our mantra is to bring these three together. And I think if you do it right, you can either scale 10x you can build something of legacy and significance, or you’re ready, you could just have a great solopreneur ship and be, you know, a three person firm, me, myself, and I, and that’s another thing I think is counterintuitive. Well, I don’t need to worry about that because I don’t have a bunch of people around me. Yeah, you do, because, again, maybe you don’t want to work Fridays and Mondays, maybe you want to take up a hobby or fishing. So the better systems, even if it’s just yourself, is the more you’re going to be able to have confidence and clarity and courage and and just the ability to get from here to there. You know, easier, better, stronger.
Scott Ritzheimer
Yeah, so good. So good. Scott. There’s. Folks listening would love to get a copy of the book, tell us about that, and then they’d also love to reach out and find out more about the work you do. Where can they connect with you?
Scott Abbott
Yeah, so, you know, we always need to give Bezos a little more money. So let’s go to Amazon. And you know, I wish I could say a bunch of other outlets, but Amazon for all the books. I’ve got my own site. I’ve got four books, but recently, Boss Up and Boss Up Moments. If your coach consultant, looking to to partner up with an organization that can help you generate impact and income, go to boss up dot coach. If your company looking to benefit from a better way to build, run scale and exit, go to boss up dot work. And then I’ve got a bunch of my own personal stuff at Scott Abbott ABC, so on the interwebs, on LinkedIn, Instagram, YouTube, I share quite a bit of information and thoughts and ideas. So those would be the locations to go to, depending on your situation and what you’re looking for.
Scott Ritzheimer
Fantastic, brilliant, something in there for everyone. Scott, thanks for being on We’re glad you’re not on a mountaintop somewhere, so you can share with us here today. Really was a privilege and honor having you thanks for coming on the show, and for those of you watching and listening, you know your time and attention mean the world to us. Hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care. Scott, thanks everybody.
Contact Scott Abbott
Scott Abbott is the Founder & CEO of the BOS-UP Coaching Solution & Academy. He is also an executive coach, angel investor, entrepreneur, and best-selling author. Over the last 35+ years, Scott has started, built, bought, and scaled companies worldwide. He has conducted more than 10,000 coaching sessions to help leaders and teams strengthen their systems, alignment, and performance. His latest best-selling book, BOS-UP Moments, blends leadership, psychology, and soft skills into a modern, visual field guide for growth in business, work, and life. Scott is known for his solution-centric coaching and his passion for unifying Business Operating Systems with AI and human development.
Want to learn more about Scott Abbott’s work at BOS-UP? Check out his website at https://bos-up.coach/
Connect with Scott through his LinkedIn at https://www.linkedin.com/in/scottabbottabc/
Grab a copy of Scott Abbott’s book BOS-UP: The Solution To Build, Run, and Scale Great Companies Leveraging Business Operating Systems + AI + Coach at https://www.amazon.com/dp/B0FCY6LTC9