Leveraging Leadership

The Four Sides of Culture: A Framework for Business Leaders

• Jessa Estenzo • Season 1 • Episode 257

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0:00 | 39:19

Matthew Person explains his Square Management System, a framework for building high trust, high performance organizations by aligning employees and processes. He discusses culture as an output, shares the importance of having a "complete square," and gives examples - like how some people prefer structured office environments while others thrive in casual settings. The episode covers using assessments to find company-employee alignment and gives practical advice for Chiefs of Staff to diagnose and manage culture across teams.


Links Mentioned:
Matthew Person’s Website


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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

 


Time Stamps:
01:15 Matt's Experience with Chiefs of Staff

02:01 Understanding the Square Management System

03:09 The Importance of Culture Alignment

14:22 The Four I's of the Square Management System

21:07 Understanding Subcategories and Levels

22:12 Identifying and Sticking to Priorities

24:32 Addressing Bad Actors in Company Culture

25:53 Using Diagnostic Tools for Alignment

37:18 Importance of Intentional Design

emily-sander_1_11-14-2025_090814

My guest today is Matt Pearson, and he is a seasoned executive. With over 20 years of experience in strategy m and a and executive management, he developed a proprietary method for creating high trusts, high performance organizations. The Square Management System is a framework for aligning employees and operating processes to create the desired corporate culture for both employees and executives alike. And he has worked with chiefs of staff. So Matt, welcome to the show.

matthew_1_11-14-2025_120811

It is great to be here. Thanks for having me. Excited to chat with you today.

emily-sander_1_11-14-2025_090814

Beautiful. And we were just talking before the air, but I am seeing your name right. It's Pearson. Even though people in the show notes might see Pearson,

matthew_1_11-14-2025_120811

That's

emily-sander_1_11-14-2025_090814

you got some different heritage going on.

matthew_1_11-14-2025_120811

It's a little mix of the Swedish heritage. That's correct,

emily-sander_1_11-14-2025_090814

Okay. So in Sweden we got the Pearson going on.

matthew_1_11-14-2025_120811

yes.

Matt's Experience with Chiefs of Staff

emily-sander_1_11-14-2025_090814

Beautiful. Okay, so folks, I did not mispronounce his name, just to be clear. So Matt is here and we're happy to have him. Um, first of all, tell us a little bit about your time working with chiefs of staff.

matthew_1_11-14-2025_120811

I've worked with a few. I worked with one currently, and um, and I think they're wonderful assets in my role, um, where I've done a few different things. My background is a little bit of a mixed bag. I've been in executive running companies. founded them. And then for the last few years I've been more on the m and a side buying and now more selling with strategy. And that's where the chief of staff comes where I have to work alongside strategic prioritization and also messaging and communication across all functions. And they help facilitate a ton of that. And of course, they'll help me with alignment as well. Um, so they're definitely a friend to the, the efforts and, uh, and someone I leverage frequently to help get things done.

Understanding the Square Management System

emily-sander_1_11-14-2025_090814

Very cool. And, uh, just jump in, jump, jumping right in here. What is the square management system? What are some of the key elements of that?

matthew_1_11-14-2025_120811

It is a, it is a great question. Uh, the Square Management system is a framework and it is designed to create output, and the output is actually culture. I know that's gonna sound obtuse, like, well, wait a second. How can culture be an output? Um, but I actually have a unique, uh, perspective on corporate culture and how it can be leveraged and manipulated to create high trust, high performing teams, as you said. And I think that's the big, uh, misconception in the, uh, kind of corporate or business world today is that, uh, what often happens is that we copy corporate culture from best places to win. And then we try to mimic those, those outcomes. And failure ensues. And so the Square Management system is designed to suggest there's a probably a different, maybe better way to affect the corporate culture for you, for your company.

emily-sander_1_11-14-2025_090814

Gotcha. So what, what are some of the, I know you've got some different, like, pieces of there, pieces of in there, as much as you wanna share, um, give people a, a taste of what you're actually gonna talk about in the, in the management piece.

The Importance of Culture Alignment

matthew_1_11-14-2025_120811

Yeah, I think the, um. The component here is, so let's go back and just talk about what culture is, right? And, and you, you acknowledge that it's for individuals and companies alike, and that's,'cause to me, culture's actually an output. It's a of a symbiotic relationship. Your, your alignment and the book I've written around this is called The Culture of Alignment. And you can, you can go on my website, town square-advisors.com and kinda learn a little bit more about that and get into the weeds. But, but effectively, culture has, in order to have good culture. You've, you've worked different places where there's been good and bad culture. I know from conversation culture is really nothing more than the individual staff members ways of doing, aligning to a degree, maybe a degree of standard deviation from the ways of doing of the company. And when those two things mesh, loves it. It's a great experience, never been better. when you're, don't mesh and it's, you can feel it when you're outside the square, as I say. Uh, it's you, you don't have alignment with the company. Your ways of doing are too different. and you don't have good culture. Neither party is bad. And that's the key thing that I wanna impress upon people and I'm gonna sidestep malfeasance, right? There's always some of that stuff that goes on, but for the most part, there is no really bad culture. There's just misalignment between people on the culture in that company. Some people love that Alpha Wall Street world, a really tough environment and some people had whore it. How can someone work for 25 years in Wall Street and love it and someone not, that's because they're neither's bad, right? They just have different ways of doing different ethics, different perspectives, and uh, and if they match, again, it's a great place to be. And that's the goal here, is to get the alignment between the employee and the company.

emily-sander_1_11-14-2025_090814

And I like what you said about it's not good or bad. I mean, I'm sure there's like edge cases here and there, but if you wanna work on Wall Street on that pace for that mission, like you're gonna love it. If you wanna go sell, um, scented candles in your own shop, that's a different pace. That's a different culture, that's a different mission. And if you're better suited to that, you're gonna be happier there. So it's, it's, you know, both, both have their place in the world.

matthew_1_11-14-2025_120811

E. E. E, exactly. A really high level example that's probably sophomoric, but at least representative or illustrative is, uh, is me. I don't like an open office environment. If you put me in a place where you said, here's your laptop, your headphones, go find anywhere to sit and do your work. No, not gonna work. Not gonna happen. For me, I wanna dress up in a suit. I like looking good at work. I, I, it makes me feel more professional. And I want an office where I can sit and think and digest and be by myself. And if I need to go talk to people, I will find a conference room and I'll walk the halls and drop in on people and stuff like that. But that's my way of doing. Other people, they want the beanbag on the floor with their laptop. cannot put those two people in different environments. They won't work. I won't make it in that type of environment. That's really high, high level. And that's actually part of the component that I call inner communication is a function of kind of what culture is. Um, but that would help the audience maybe understand kind of what I'm getting at when it comes to ways of doing.

emily-sander_1_11-14-2025_090814

Yeah. And, and another way I interpreted what you said when you were like, culture is the output.

matthew_1_11-14-2025_120811

That's

emily-sander_1_11-14-2025_090814

And in some ways I thought of culture as the input. So a lot of companies I work for are like, here's the spreadsheet, here's the numbers. Now drive the numbers. Into the culture and into the workflows where I see it as people, you know, get, take care of your people, make sure they're trained up. You have a good culture, you have a good foundation. And then they will in turn take care of your customers and more customers buy more things, and that will impact your top line revenue. And it starts with the culture. Like culture to me was the foundation and input, but you're kind of talking about it in a different way.

matthew_1_11-14-2025_120811

That's right. I, I agree with the, the, the, the chain. Uh, inherently that is true. Uh, and I think that's why culture, I call it the double down on culture. That's why it's so important because if you have good culture, then staff do good things, which creates a higher performing team, which creates more revenue, which creates scale. That is the whole point. But how you get to culture, I think has to change. And the example I would give you on, on why I see the problem in the market. After all the companies that I've talked to, hundreds of them every single year and have seen the good, the bad, and the ugly, there's a couple things that pop up. One, there is no such thing as a hiring manager, whatever role that person would be, who has said that their culture is bad. you ever gone? I would love it if an audience member raise called in and said, actually, I've been somewhere where this had stuff. This is gonna be a tough place to work, Emily. I I don't think you're gonna make it here. I mean, only the strong survivor. Like that's never happened. Everyone's like, I love it. This is amazing. The best culture in the world, right? So you have that on one end and then you have, uh, employees. And my favorite phrase is, no employee starts their first day disgruntled. It just doesn't happen. Everyone's like, I love it. This is great. I got a new job. Now maybe that's is always true'cause sometimes people just have to take a job to, to pay the mortgage and pay the bills. But for those who have the luxury of choice, it's usually a very like excitable moment. However, will show that almost half of new hires, they don't make it 18 months for whatever reason. Maybe they quit, they get fired, something happens, they don't make it. So obviously you've got these two positives, right? it's not working. People aren't surviving. So this culture fit that we talk about, we're hiring for vibe. Emily's an awesome person, she's gonna fit in here. We don't know that and neither does the employee because they really don't know what the company's like. They only get a little bit of of a touch. And so what if you could do better hiring your employees? And what if you as employee could know a little bit more about where you were successful? And that's the point here of the framework. That's why I call it is an output. Square management system is a framework. It is a system help you with that.

emily-sander_1_11-14-2025_090814

Beautiful. And on that you have a, an assessment, a free version, and then a paid version to help give people and companies a sense of like, okay, is this a good alignment? Is this a good fit? You know, let me find out more about myself and kind of my inclinations and my wants and needs. And so I took. The assessment on, uh, your website,

matthew_1_11-14-2025_120811

Perfect.

emily-sander_1_11-14-2025_090814

I like, you'll know, like, my score was four, which means mostly bs. So it says moderately constrained independence. You like a blend of structure and freedom. You're collaborative, adaptive, and work well when there's room for input within a shared framework. So

matthew_1_11-14-2025_120811

Yeah,

emily-sander_1_11-14-2025_090814

me what that means.

matthew_1_11-14-2025_120811

box mi middle to maybe a little bit more on the free end.'cause the four is, is a higher end on a one to five to scale, you're probably more on what I would call a, um, more of a light degree of constraint. So before I, before I opin on that, I'm really glad that you took the quiz.'cause I think some people take it and they're like, yeah, that sounds right. But I didn't think about it that way. also would say is, did you answer the questions honestly?'cause a lot of talk to a lot of people and they, some people have said this, I wanted to answer this way, but I really answered this way'cause I thought that was more appropriate. And I was like, no, no. You should have answered the first way.'cause that's really you. That's actually the real you is the first

emily-sander_1_11-14-2025_090814

I answered, honestly, I always take, I'm like brutal honesty, like give me the real deal. So yes, that was true to form.

matthew_1_11-14-2025_120811

Well, there's sides, right? There's, so there's, the reason there's a spectrum here is that constraint is, is um, is what I call constraint. Independence is actually culture, and it exists on a, you know, on a spectrum. And the audience might say, that sounds caustic, don't constrain my independence. And, uh, and yet at the same time. That's actually what happens in companies. So imagine Emily, if you went to your first job and you were like, I, I had no constraint. You were, you just had, you could do whatever you wanted. Okay. That's impossible because in order to meet delivery standards, to meet compliance and regulatory standards, there has to be guardrails and restrictions on what you can and can't do to, to actually have a working business, and that is the constraints on your independence. what is that? That that's systems, that's processes, that's ways of doing. Right? And some companies by default have to have what I call a high degree of constraint. Think of hospitals, for example. My sister's a doctor. If you don't actually follow the rules there, like people die. So there's not a lot of room there. You're in a little bit of a box. You're more execution oriented. Other companies like VCs, startups, they're more loose and other companies try to be more flat, more loose. That's a light degree of constraint. So constrained independence. Is really the culture is really the employee's known and communicated degree to which they can action their own ideas. That's as simple as it is. What degree do you have to do your own thing at the company? And if you know the guardrails that you can operate in, and if everyone else knows the guardrails that they can operate in, well then you start to get everyone in the same square. You're all playing in the same sandbox. And why is that important? Well, first off, you don't have to sit there and go, Hey, can I do this? Can I do this? Can I do this? just kind of know, right? You can, you, you know what you can do, so you can move faster. when you're empowered to action, you can make micro decisions because you kind of know where you can and can't play. You only have to go and ask when you're outside the box you don't, and so you can make micro decisions. You're empowered. You feel like you have an output, you're an impactful employee, and people love that when they feel like they've had, even if it's a small piece. They feel like they've actually contributed. If you know that all your other employees are in the box too. Then you have trust. You don't have to worry about, well, is this person really giving me the right answer? Are they just trying to, you know, a lot of that office politics comes into play. A lot of that goes away when you're all inside the the box. And when you have a higher profess faster worker who's empowered to innovate within a known degree and who trusts all the other employees. Well, they're pretty loyal'cause they're pretty happy'cause they're inside the box and that's how you get the aligned office. You get the ways of doing that. Everyone is on the same page. You get that fast removing high trust organization. And so the now what you need to do is you need to determine the size of the box.

emily-sander_1_11-14-2025_090814

Hmm. And what about people in different roles within the company? I mean, I've been in companies where like, look for a new hire for like a frontline analyst position. The bo the box might be smaller to start with. Like you might more have more constraints. And as you move up, if you manage a team, if you manage a department like C-Suite, you know, you get, get a broader scope. Is there, you know, adaptability within the framework for things like that.

matthew_1_11-14-2025_120811

There is, and it's definitely designed to be more of a company-wide. Framework at the same time, it's applicable at the team or department level as long as it adheres back to the company level. And, and what I can get into are some of the problems that companies have and what I call fiefdoms or mini squares where departments have different ways of doing and then all of a sudden you've got chaos, right? And you don't want that. So teams, departments, they still have to have an association back to the mothership. And you're right, some rules are heavy constraint.'cause you just, you're too young, you can't. Make those decisions. It's less about the individual position and it's more about the company wide and for a certain, certain levels and experiences in the system. At the same time, it does factor because like for example, onboarding that impacts junior and senior at the same time. So how you do those things is part of the culture for any level.

emily-sander_1_11-14-2025_090814

And I think you can still have the same ethos where it's like, hey, generally we wanna give people latitude to be as independent and have agency within their kind of realm and be a, be a decision maker within their role.'cause they're closest to the information or customer or whatever. And then we just know that like when you're a new hire in this role, you, you have less experience. So we're gonna have to give you a little more guardrails, but you can still have the same kind of, uh, ethos or motif or kind of, uh, guidance.

The Four I's of the Square Management System

matthew_1_11-14-2025_120811

of the things around culture, especially at the junior level, let, let's dig into what those things are, right? What, what are the four sides that actually constrain you? Because some of that is relevant to a junior employee. Um, you know, independence is what I call the fifth eye of this square management system. That's the output. And that's your, that's your square score. That is your known degree. And imagine if you knew the company's square score and you knew your square score, then you can kind of figure out pretty quick if you were gonna fit right. And you're like, whoa, that's a really hard concerned environment. I don't wanna work there. Or, whoa, way too loose, too much freedom. I just wanna be told what to do. I don't wanna work there. That would be amazing if that ever took off, but. Let the, let's say the four i's, what are those? The first i's identity, and it's where every company would start, right? That is your, uh, organizational definition. That's your mission, your values, your brand personality, your core beliefs, right? And the key question there is do our staff and our customers know what we stand for? Why, and there's 10 elements within, uh, identity. Then you have instruction and, and that kind of connects.'cause your brand does kind of signal who you are for the rest of the system, right? If you're a highly modern, innovative system company, you're gonna have a different way of doing a different level of instruction or association, right? There could be that mismatch. If you have an old logo and you're old timey, you're gonna have a different association. Brand personality. It all connects for a reason. But the next one is instruction. That's how you operate and that is the clarity and consistency of expectation. That is your onboarding, your knowledge, transfer systems, your training, all that stuff matters to junior staff. Let's say you work somewhere and there's no training and you're like, whoa, wait a second, I'm just stuck. I'm not gonna develop as an employee. That happens to some people, right? So that's part of how you, your experience at that company. The key question with instruction is, are the roles or the expectations are the processes clear and scalable? Are they known? Um, the, the third one is what most people think, uh, culture is, and that's inner communication. That's your Thursday off happy hours and your ping pong table that everyone kind of associates with color with, with, um, with culture. this is really actually how people interact. It and how information flows through the company. It's your hierarchy structure. It's your meeting cadence is where hybrid, you know, working five days a week or not comes into play. It's communication tools and tone too. Some places are really serious. Some people have no negativity, can't talk negatively in that office, right? So that, that's your third side and your last one ties it all together. This is the information feedback, the fourth eye. That's how you use information to learn and adapt. Um, are we doing, are we using it to adapt and are we using it to stay competitive? It's individual performance. It's also corporate self-assessment, which I would argue doesn't happen very much. And all those sides come together in varying high level or low forms to create the systems that make your company

emily-sander_1_11-14-2025_090814

So you've got, it's a square, so there's four sides which correspond with the four eyes you just described. And then the company culture will, will. Basically have a have a, a life of its own or the score. I'm looking at my assessment score, like I have a four, so I would wanna be aligned with the company that has like maybe a four score as well. Is that the best alignment for me? Sure.

matthew_1_11-14-2025_120811

Within a degree of deviation, right? This is not binary in the sense that you're never gonna get, because a listener's gonna be like, that's great, Matt, for one employee, but not 400, 4,000, 400,000. At the same time it, that's why it's called a square. You just need to get everyone kind of in this same standard deviation box. So you could be, you know, a three and still survive at a four, but you're not gonna make it if you're a two. Right? That's probably too far.

emily-sander_1_11-14-2025_090814

A one should not. Yeah. Okay.

matthew_1_11-14-2025_120811

to be at least close enough on your ways of doing to be okay

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

output of culture in that company.

emily-sander_1_11-14-2025_090814

And we just talked about the fact that. Having a one company or a culture and having a five is not inherently right or wrong, bad or good. It could be a hospital or it could be, you know, a startup type of thing. If a chief of staff is listening and saying, okay, I understand that is, is there room for, we wanna create? A congruent culture. So, you know, across all teams we are espousing the same things. We're talking, um, about the same mission statement. We're all doing different functional groups and functional roles, but we're rolling up to something consistent. Is that where some of the chief of staff work and, um, interdepartmental initiatives and communication channels and all those things come into play.

matthew_1_11-14-2025_120811

And actually a chief of staff person alongside maybe HR, are probably the people who would benefit most from understanding the system because they connect all the pieces and, and oftentimes what I see in executive teams are people who are really good at their one core function, but maybe haven't learned yet because they've been stuck in marketing or sales, and they don't really understand the interconnected nature of business. That, that they don't really start to make decisions outside of their own function. They just think about themselves and, and then when you get to a certain level of leadership, all of a sudden you're supposed to take your, your function. that across the business. People can't do it. And so part of what this, this book does is explains to people all the interconnected functions that need to kind of coalesce or align in a uniform way because, uh, a chief of staff actually will see all the functions and could probably figure out where good is and where bad is, and help figure it out. The framework's really a diagnostic it's, and if you deploy it, because each side has 10, 10 questions and then a score for each one. You can have this executive team, senior, middle, and frontline, take it and compare and contrast their answers on what they see as how these elements should be deployed or how they're actually being deployed currently. And you'll figure out really quickly where you have a problem in the company.

emily-sander_1_11-14-2025_090814

What happens if you're like a chief of staff and you're like, this assessment's cool, everyone take this assessment and we all get our scores and we're like, oh, we have like one through five on our executive team. Like what do you, what do you do then?

matthew_1_11-14-2025_120811

Oh, like too much variance. Too much spread. Well, it would, it would tell me you have no system, right? You have no alignment then. But you probably, honestly, if that was to to occur, probably have more of a chaotic business because then you have people fighting with each other over what the right way to do stuff is. You have way too much delta between those points of views to actually have harmony. How would you be able to progress with institutionalizing standards and procedures? You'd have different stuff everywhere.

emily-sander_1_11-14-2025_090814

Because I'm thinking like, you know, chiefs of staff often come in, they inherit a team and they're like, okay, let me kind of assess, you know, talent assessment and what have we got going here for leadership skillset, culture org chart, whatever. And if, I'm just trying to think out loud here of applying, um, your assessment, you're like, oh, oh boy, we have a huge variance here.

matthew_1_11-14-2025_120811

That's right.

emily-sander_1_11-14-2025_090814

Do some people have to get off the team or do like, how do we kind of reconcile that?

matthew_1_11-14-2025_120811

Yeah, there's a, so there's a couple rules and we'll get into problems with companies in a second, but there's a couple rules for the square management system to make it work. Uh, one is you have to have a complete square. It doesn't work if you don't have a complete square. And that's the biggest, actually, actually that's the biggest problem companies don't even know they have a square to make or, and because what happens if you, if you don't have a complete square, who fills the vacuum nature of pours the vacuum, right? Someone's gonna fill, the employees will decide, or departments. That's where we get the mini square is the problem. Somehow someone's gonna make a decision and it's probably not gonna be the one that the executive team wants. And, and so that's a hu That's the reason why you need to do this, is you need, you need to have a know what the complete square is. The second problem is adherence to it,

Understanding Subcategories and Levels

emily-sander_1_11-14-2025_090814

So just so people know, to know, to know the complete square you're gonna go through, you're gonna go through Matt's book and do like the 10 individual items of eyes, right? So you got the four squares correspond with eyes he just described. And then within those, you've got different subcategories that will,

matthew_1_11-14-2025_120811

apply it. Right, exactly. A high, medium, or low level. I give you insight into what it looks like to deploy said element at a high, medium, or low level of

emily-sander_1_11-14-2025_090814

Okay.

matthew_1_11-14-2025_120811

You can understand what you like or believe is the right way to do it. You can do this online too and take the quiz and it'll, it'll help you kind of figure out like, Hey, this is what I think I should do. This is great. As for founders who might have IP but have never figured out like how to run a company.'cause a lot of them are tech people and that's not a negative. They're very smart. They built something useful. But they haven't gone through an MBA or they haven't gone through a co building, a running a company. What do I do? This will tell you exactly what you wanna do because you can go through and pick and be like, I'd like to do this, I'd like to do that. And then you can see what the element is. Now the how is up to you, you gotta go do it yourself. You, you gotta go do it. But this at least gives you the framework for what, how. like, and that's the difference between this book and everything else. A lot of business books just give you theory. This is a theory. In short, it's very short on purpose. I call it a pocket guide, but it's really meant to be a how it's meant to be actionable. So anyone can pick it up and go, we're way off. How do I fix it? That's what that looks like. I'm gonna go do that. And that's what the point here is.

emily-sander_1_11-14-2025_090814

Yeah, a classic question I get from chiefs of staff, another executives too, is, Hey, I would like my, like I ask, what are your top priorities? And they list like 17 things. And then I ask like their colleague and they list 17 other things. I'm like, okay, first of all, time out. We already have a problem. So would something, how would your, how would your system interact with like, let's identify our top priorities, um, and then let's stick to them. It would, how would that interact with your model?

matthew_1_11-14-2025_120811

going through this, uh, currently where we get what we call Drift. Okay? And one of the elements in identity is mission, and the other is product to mission fit and product to mission fit is really, are you on or off strategy? Because your mission should guide and set the strategy and then you against that. And you always have to look back and be like, is this really. Is this really on strategy or is this off strategy? How does this actually parlay to what we said we would do or who we are? And a lot of people come up with all these ridiculous ideas and then they try to figure out how to make it swing back. But product mission drift, E, each element has like their one core thing that companies do wrong more than the other elements in identity. It's product, mission fit, it's going off strategy. And you would, in some cases, companies don't set themselves up for. Variance because this is not meant to be so binary that you can't flex with market dynamics, right? So if you set yourself, some companies, they're, Hey, I am this, I'm gonna be what I would call ha, hard level of constraint on my brand identity and my product and mission fit, because that's who we are. never gonna change. And that's okay for some companies though, who need to respond. You want maybe a moderate and that changes then your communication and your instruction so that when you do pivot and you go a little bit off strategy, it's not really off strategy'cause you've kind of communicated we're gonna be in this broader arena. So how you set up your brand and how you set up your communication will dictate the level to which you can then have strategic fit spread or not. And that's how you control all these different things you're doing. They all have to tie back. To product mission fit.

emily-sander_1_11-14-2025_090814

Okay, so you didn't identify that through your system, you can identify the the what and implement the how. Um. Real life scenarios would be executive has, um, a difficult boss or a difficult colleague. Does this help identify or address that, or is it just like, Hey, he's a four and I am a one, so we're just gonna be different in that way?

matthew_1_11-14-2025_120811

Well, so that it does help identify that. And, and one of the common things that I talk about at AT Problems and Company and where culture goes awry is when you have that one bad actor. You know, oh, Emily's she's the best seller out there, but she's terrible. She abuses people, she's awful. And yet no one fires Emily because

emily-sander_1_11-14-2025_090814

I sell stuff.

matthew_1_11-14-2025_120811

revenue. Right. She's awesome at selling. So that though is where things go awry, because then what does that tell the rest of the staff? It means that you really don't have a border for what is acceptable or not acceptable behavior. You don't have a judgment system. You only value output. And so you can't then say, depending on what your mission or your values are, or your vision, right? You can't have like where, you know, uh, put in, insert whatever verbiage you want to about how you're supposed to behave, and then have a bad actor who's completely deviant from that, right?

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

would have to then have the constitution to adhere to what you said you'd do, and. You have to realize your square's not for everybody. And that that's the hardest part. Emily May not fit. She's a great seller, but she may not fit the culture and you have to just be like, listen, she's not gonna work. Because inevitably what happens is there's always someone else who can sell as well. There always is. No one person is so critical that the whole company's just gonna fall apart. And if that's true, then you haven't managed your staff the right way. You haven't put your

emily-sander_1_11-14-2025_090814

A bigger problem.

matthew_1_11-14-2025_120811

yeah, you have a

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

haven't structured your company the right way.

emily-sander_1_11-14-2025_090814

Yep. So you mentioned a diagnostic tool. So would you suggest using this for like when you're first getting started and here you're going into a brand new company, set this thing up at the beginning and then the people you bring in make sure you run this as assessment for alignment. That might be one that maybe one use case.

matthew_1_11-14-2025_120811

Yep.

emily-sander_1_11-14-2025_090814

also thinking there's so many, obviously existing companies, existing teams do come in new, you're trying to reset a team, you're trying to reset a culture. Um. It sounds like it can be used for that, but there might be like, Hey, at the end of the day, some people might not survive. You know, the we're, we're this culture and you happen to be kind of outside of that. And it doesn't mean good or bad, right or wrong, but hey, you either can kind of conform to this or we can part part ways. Is that

matthew_1_11-14-2025_120811

Exactly.

emily-sander_1_11-14-2025_090814

down? Okay.

matthew_1_11-14-2025_120811

it's, it's a diagnostic for in, in a few ways. One, it, it should be used on, on hiring, on every person you bring into a company. I can't tell you the number of roles I had where I've had to take tests. To have a

emily-sander_1_11-14-2025_090814

Yep. Yep.

matthew_1_11-14-2025_120811

and they're part of, uh, your, on your, uh, hiring process. And you should, HR departments should quiz people to determine where they fit on the spectrum, because you can't have people on opposite ends of the spectrum. It's never gonna work. It's just never gonna work. And the, the problem we have is culture's gone so broad that square's gotten so big because everyone wants to be so nice. And I, and

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

terrible to some people we've gotten so. Generalist that the box is so big that everyone should fit into it. But at the same if you do that, you really don't have culture then at all. You're just kind of just making it so broad and so big that everyone fits in. That's not really, that's not gonna work, uh, for obvious reasons. And so it should be it that way. And then two is if you are an executive staff and you've never really thought about it this way, you should take the quiz and, and look at it two ways. One is how your company is currently structured. Because there, there is at some form, there is like an actual structure that's in place, whether you realize it or not. And then you compare that to what you want to be, then that becomes your strategic prioritization, your projects that you would then undertake to then go fix it'll, it'll, it'll clearly highlight where you're off and uh, and then you can go fix those things and those become your strategic projects.

emily-sander_1_11-14-2025_090814

So if you're a CEO and you're using this on an existing company and you go, Hey, look, we're doing pretty good, but here's this one spot where there is a gap, there's a delta, and you come up with like, for the next 18 months, we're gonna address it in this way.

matthew_1_11-14-2025_120811

Yep.

emily-sander_1_11-14-2025_090814

that a use case? Okay.

matthew_1_11-14-2025_120811

A hundred percent e exactly. In the back of the book, I actually have the 90 day use case structure where how you, how you would fix your company in 90 days. You can't fix everything. You gotta fix, you know, the high priority things and the system will identify the spread. Um, but that's exactly the point. This is a diagnostic to help you understand where you're off and how, and how to then fix it with, with the varying levels of constraint for that element. I am sure that someone reading this will go, I don't, I think you should add this element. Fair enough. Go ahead. It's not fixed, it's not designed to be perfect. This square is what matters. You wanna change the elements that are inside each, each of them. I've given everyone a, a starter of 10 elements that I think are pertinent to pay attention to, but, but you could easily add more or you could add, you could remove some you don't think are helpful. But it, but a system and a complete square is more important than none.

emily-sander_1_11-14-2025_090814

And it seems like the, the biggest thing you're measuring is the constrained and independence kind of axes,

matthew_1_11-14-2025_120811

Correct. I am

emily-sander_1_11-14-2025_090814

Mm-hmm.

matthew_1_11-14-2025_120811

just trying to get to a known border across the company to consistent diagnostic. You should do this quarterly or at least bi-annually. So that you see where you are to make sure you're not off track, you're not going, you're not deviating from what you said you would do. And that consistent maintenance is part of information feedback, but it also just is, it is just helpful to, to make sure you're doing what you said you would do. a lot of companies don't pay attention to this and then they go off track.

emily-sander_1_11-14-2025_090814

True story. So we talked about A CEO using this also as an employee going into something you might say, Hey, let me at least get this data point on myself, even if this company might not use this system. But then I can kind of, you know, ask questions, read between the lines and say, Hey, am I a good, am I a good fit? Am I a good cultural alignment too?

matthew_1_11-14-2025_120811

right.

emily-sander_1_11-14-2025_090814

This perspective company.

matthew_1_11-14-2025_120811

Exactly. So yeah, you can use it individually and there's a component to which an individual would wanna know who they are to align to the company. And then for chief of staff, who's a lot of which is reporting right, and diagnostics and business processes. This should be part of your regular dashboard. And a quarterly or ally update to, to check in. And then that becomes the projects that as chief of staff, would then go initiate and run, Hey, we got a problem in instruction. The drivers are clearly not paying attention to the rules and regs. What's going on with our onboarding? Are we off on onboarding? We might be off on our onboarding. Let's go fix that. And like, that's how you fix the company. Um, I know it doesn't sound. Warm, fuzzy.'cause a lot of people wanna talk about culture is, is you know, this nice thing, right?'cause culture feels nice and, and to quantify it and to call it constrained independence doesn't feel, it feels rigid, right? But at the end of the day, if I look at all the companies that I've worked with, that I've looked at buying that I've run. The most aligned businesses, the ones that are the fastest moving, like you can feel it when it's, it's easy to get stuff done. You can tell. And I look back and I can tell you the companies I've been at where I was like, holy crap. I didn't, I didn't write the book then. I didn't really have the concept to, to, to define then. But man, that was a really aligned business. And you know, when you're way out of alignment and you can tell really

emily-sander_1_11-14-2025_090814

And I think I, and I, yeah, thank you for saying that. And I think that boundaries, if you don't have boundaries, you're not distinct. Like you're not distinct from anything else. If you're just like, okay, we're, we're everything, we're, we're, you know, culture, happy, soft, cute, whatever, but people want to. I mean, people wanna stand for something that might not be the best term, but they wanna stand for something and be distinct. Like, here's our company's culture and here's how it's different and you know, better or just unique. And so if you don't have boundaries or distinctions around that, then like, okay, what are, like, what are we doing?

matthew_1_11-14-2025_120811

You, well, someone will then set it right, somehow it's gonna get set. It's just not gonna be what you want. Or it'll be variants across the company. And then that's when you have disarray. One of my favorite stories was a company I worked at years ago, uh, where one department, the finance team, they had to, they had to go to work five days a week. They had to be in the office. Everyone else, one. And can, you can ima, and that sounds trivial. You can imagine the degree of problems that that caused and the turnover. And everyone started pointing fingers and how can you let this happen? And no one fixed it. They were like, well, that's how the CFO wants to run his department. Whoa. Major deviation and corporate policy between one function and the other. And it caused all kinds of problems. Um, and that's very simple, and I know, you know, return to work is a huge concept right now. But I'll say this, for those who do institute that change and say, Hey, listen, we're gonna make you come back to work. We said you could be remote now you're gonna go in three days a week. You've changed the square. The employee didn't change the square, you changed the square. And you cannot then sit there and say, well, hey, Matt's not gonna go to work and I don't wanna do that. I'm gonna quit you. You have to expect that that's gonna happen. Do a chunk of people who are just gonna be like, no, I, I don't want to go to work. I like the way we said we were doing it. And you have to accept again, this square changed. Not everyone fits the square and they're gonna leave, and you have to accept that.

emily-sander_1_11-14-2025_090814

And that's fine. And that's okay. I think that's okay. People are so scared of that. Well, I mean, if it's not a good fit, it's not good for them or it's not good for you. So it at some point, you know, literally, like, not literally, but drawing a line, like drawing a line in the sand. Like, this is our company. This is what it means to be on this team. This is what we value and this is what we hire for and this is what we expect of our team members. This is just how we run things. So I think, um, yes, of course there's, um, all the other. Quote, unquote softer elements of culture that, that have their place. But it's also, you know, I think

matthew_1_11-14-2025_120811

Yeah.

emily-sander_1_11-14-2025_090814

for something and being distinct is important too. Circling back to my assessment, so I'm, I was score four, mostly Bs, moderately constrained independence.

matthew_1_11-14-2025_120811

Yep.

emily-sander_1_11-14-2025_090814

so I, I did answer these truthfully, like, what else can you tell me just about, uh, about my score here? I, it seems like I kind of want some sort of framework, but I want a lot of latitude within that. That's how I interpreted that.

matthew_1_11-14-2025_120811

Uh, exactly. I think I would interpret that as you need to know what you can't do, but you'd like to influence what you can do. And, and that, that I think is probably common. I think most people I talk to are, and I'm that way. I don't, I'd like to be able to have impact, influence to a decent degree and come in and be like, let's change this and do this. But I also wanna know what the hard line of the sand is. Like, you can't, you gotta stop here. Okay, cool. bounce against that. know? And so I think that's, that's probably who you are as a person. You need to have some level of influence'cause that's how you feel valued.

emily-sander_1_11-14-2025_090814

Hmm.

matthew_1_11-14-2025_120811

If you didn't have the ability to affect the comp, what was going on around you, you wouldn't feel useful. That's probably why you were chief of staff, right? And, but you also wanna know what, what you kind of, Hey, this is, guys, this is the rules. We gotta stop here. So there's a, there's a variance there.

emily-sander_1_11-14-2025_090814

And I love what you said because the, the way you feel valued, people feel valued in different ways. But if you have that alignment where the company is like they value what you do and what you bring to the table, and then you know that you're providing something of value, I think that's, I think that's a mutually beneficial dynamic as well.

matthew_1_11-14-2025_120811

I think for people who are in the middle, too much freedom becomes claustrophobic. I feel that way. I'm more, a little more in the middle. I'm middle, middle to loose. If you don't tell me, then I'm either going to fill the void and I'm gonna make the box. Right. You know, or I'm gonna struggle because I'm gonna be like, well, I don't wanna get in trouble, And do something I'm not supposed to do, but you haven't told me what I'm supposed to do, so how am I supposed to act right? What is the actual, what does good look like? And then I'll just make it up.

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

Uh, and that's, so that's me. Uh, and that's what a lot of people are probably like.

emily-sander_1_11-14-2025_090814

Would you say most chiefs of staff would be kind of in the mostly B category? Is there kind of, um, different, different trends along different roles like supporters or.

matthew_1_11-14-2025_120811

way. I haven't thought of it that way. You know, that's a good question. I haven't gotten there. Maybe in my thinking around like, are there roles or personas of people who, who probably like it. I, I came up with that off the top. I'm like, yeah, chief staff like to affect outcomes and that's probably why you ended up that way.

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

and there are some people who don't wanna affect outcomes. They just wanna be told what to do, and

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

They, they like just, I don't tell me what the box is and I'm not gonna change a damn thing.

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

a hard lesson for me as a, a manager of people was understanding why someone didn't wanna advance in management. They just wanted to go do output. And I have tons of friends who were like that, who were like, I don't, I remember a good friend of mine who said, I got forced into managing people and I hate it. And I was like, you kind of are at an age where you're kind of can't be like. kind of progress in your career. Like you're kind of, and he's like, no. He's like, I, I don't

emily-sander_1_11-14-2025_090814

I don't wanna.

matthew_1_11-14-2025_120811

I don't wanna, I don't wanna do

emily-sander_1_11-14-2025_090814

Sure.

matthew_1_11-14-2025_120811

be an individual contributor and I could care less. I'm like, you're gonna tap out on your career. And he is like, that's cool.

emily-sander_1_11-14-2025_090814

Yeah.

matthew_1_11-14-2025_120811

other things I wanna do with myself. And, and that was hard for me to understand as, as a leader of people. Like not everyone is that way.

emily-sander_1_11-14-2025_090814

I went through that same thing and then I realized, you know what? I need people on my team who just wanna be a fantastic IC because if I want, if everyone's trying to get promoted, then I have a different problem. Um, so I was like, actually, I actually appreciate and respect folks who are like, I'm gonna do a really good job for you, Emily, in this particular role.

matthew_1_11-14-2025_120811

Yes, that's

emily-sander_1_11-14-2025_090814

Gotcha. Gotcha.

matthew_1_11-14-2025_120811

and, and that's, that's helpful because that helps you manage people.'cause you can't have, imagine if you had a whole entire team people who all wanted to be CEO

emily-sander_1_11-14-2025_090814

Yeah,

matthew_1_11-14-2025_120811

that would be,

emily-sander_1_11-14-2025_090814

problem.

matthew_1_11-14-2025_120811

and

emily-sander_1_11-14-2025_090814

Yeah. Another problem. Yes. Uh, beautiful. Matt, anything else that you wanna get across or people need to know about, about the Square Management system or what you do and who you work with?

matthew_1_11-14-2025_120811

Yeah, I think there's one key concept around it, and that's intent. This is intentionally designed. It's not an accident. It's not just a default outcome. It is something that a group of people, or a CEO or however you want to put that group of people who determine this together, it is something that you've intentionally done, that you've acknowledged needs to be done. that will help then get the system together and adhere to. I think we have, as I started this conversation, we have defaulted to copying other people. We've looked at what success looks like to other people. A lot of business books are theoretical and they give you attributes and those are great, and you need to know what good looks like, but it doesn't mean it's gonna work for you or your situation or what even maps to what your unique circumstances are. You have to intentionally want believe that this is something that you should construct. Corresponding as individuals, you gotta sit back and go, stop chaing myself into fitting into a job that maybe doesn't work. who you are, where you like to work, what you want, what, what does good look like to you from an environment perspective, how do you best succeed? And I think if people were both companies, individuals were more honest about that and more intentional about that, we'd probably have better outcomes. We'd have better run companies, we'd have happier employees, we would be better at work. So that's the goal here is intent. Intentionally try to do this.

emily-sander_1_11-14-2025_090814

Beautiful. Matt, where can people find out more about you? Find your book. Your website again is.

matthew_1_11-14-2025_120811

Town square-advisors.com. You can take the free quiz, you can deep dive into all 40 elements in the, uh, in the methodology. And you can sign up for an advanced copy of the book I'm currently undergoing. Uh, kind of line edit copy review right now, editing it and it should be out. Figures crossed, like end of Q1, Q2. Publishing is interesting. World takes longer than you think, but probably sometime next year.

emily-sander_1_11-14-2025_090814

Beautiful, and we'll have all that information in the show notes. But thank you, Matt. It's been a pleasure.

matthew_1_11-14-2025_120811

And it's been great talking to you. Appreciate the time.