July 29, 2025 • 26 mins
Caroline Biesalski welcomes Matthew Person to explore the development and refinement of the Square Management System. They delve into the concept of company culture and the idea of constrained independence. Matthew discusses the use of the Square Management System Survey to identify and address cultural misalignments within organizations. The conversation highlights the advantages of implementing a structured management system and the importance of building alignment and trust among leaders. They also touch on the significance of executive self-awareness and goal setting. The episode concludes with Matthew's final insights and a special offer, followed by Caroline's closing remarks.
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Episode Transcript
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(00:00):
And so I think people need to deep dive intotheir own personal partialities about their
(00:05):
working environments where they found success.
And I think companies need to understand whatsuccess looks like in their organization and
actually stick to it.
The the point is you you do this at a survey,the 40 survey at the executive level, senior,
middle, and frontline, and you can very quicklysee as a diagnostic tool where your company is
misaligned.
Moreover, you can take the quiz and look at itand say, this is where we are now.
(00:29):
And then take it again and look at, this iswhere I wanna be.
And you'll understand the elements you need tochange.
Welcome to Inspire Choice today.
I'm your host, Caroline Biseltzky, here tobring you authentic stories, surprising
lessons, and powerful takeaways to fuel yourjourney in business and life.
In each episode, I'll take you from oneinspiring guest to the next, blending their
(00:52):
experiences with my expertise to uncoverpractical strategies you can use right away.
Whether you're starting out or stepping up,stay tuned for insights and actionable tips
that make a difference.
And stick around until the end for a specialfreebie just for our listeners.
(01:13):
Hello and welcome inspired podcast community.
This is your new episode.
My name is Caroline and my today's guest isMatthew Pearson.
I'm so happy that he said yes to our interview.
How are you doing today?
I'm great.
Thanks for having me.
Really appreciate it.
Thank you so much and I would like to introduceyou to the audience.
(01:36):
Of course, you are a seasoned executive withover two decades of experience in M and A.
That stands for merger and acquisition, right?
Yeah, a cross between M and A and executiveexperience as well.
And then strategy and high level leadership.
You are the creator of the Square ManagementSystem and author of the upcoming book The
(01:59):
Culture of Alignment where you explore howtrust and structure can transform company
culture.
Welcome to the inspired podcast Wow!
Matthew Pearson.
Thank you for having me.
Pleasure.
That's so great.
My first question for you is, what inspired youto develop the Square management system?
(02:20):
And how does it redefine traditional leadershipframeworks?
It's a great question.
This is something that I was pushed into.
And so in many ways, I'm a fitting guest foryour, podcast.
When I answered an interview question maybeeight or nine years ago, I was asked, how would
(02:40):
you affect organizational culture and alignmentacross, you know, six, seven hundred employees
who were in four offices in three states?
And my answer was the beginning of what becamethe Square management system.
If only because the recruiter said it was themost unique answer that had ever been given to
that question, and then I should probably dosomething with my logic.
(03:02):
And to me, the logic stemmed from my experiencemanaging professional sports franchises and
array of people in disparate roles.
And, you know, that was just how I approachedit over the years.
Would mention it to people and they would kindof say the same thing.
That's in that makes sense, but you should dosomething with that.
That's interesting and I needed to develop it.
(03:23):
And so I pinged people along the way.
I pinged other offers.
I pinged executives.
I pinged publishers.
Does this make sense?
Would anyone like to learn more about this?
Is this actionable?
And I got advice from a lot of people along theway, and they pushed me to continue to develop
it.
And it took a long time, in part because I hadother obligations, but in part because I needed
to think through it.
(03:44):
As I saw my different life experiences from acareer professional experience, come forward, I
saw the applicability become more and morereal, and it refined a lot of the way I thought
about it.
And I finally actually had enough cumulativeexperience to put it all together in a more
actionable framework, and I finally wrote thebook.
But I needed that time to go from idea tostructure in order to to get to where I am
(04:09):
today.
And so I had inspiration from a lot of peoplewho enjoyed what I was talking about and help
test and and kind of reframe the way I wasapproaching it.
Oh, I love your answer.
Thank you so much for explaining to us.
It sounds like you did a little customerdiscovery at the beginning to see, how they
like it Or
(04:30):
I did.
Well, I did some I did some discovery, and Iused it, and I applied it.
And I knew it would work based on my priorexperience, but it needed it needed rigor, and
it needed adjustment.
And so and then, of course, the act of writing,it helps refine things.
Then you have to really make it actual,digestible, understandable.
And so it it it kind of morphed over time as II put it together to something that maybe was a
(04:53):
little bit more of a complete package.
You know, why does this work?
In of in short, you know, the problem withorganizational culture right now is it's common
sized, and it's also one directional, which isreally the company perspective.
And a lot of companies say, hey.
We're gonna go look at the best places to work.
In in a lot of business books, they just teachyou to copy.
(05:14):
I I interviewed a thousand companies.
I talked to 800 CEOs, and these are theaggregate things that we learned about those
collective groups of people.
We've kind of averaged it out and said, youshould if wanna be like them, you should do
these things.
Well, copying someone else's work doesn't meanthat it works for you.
And then also, and from an organizationalperspective, it negates the input of the
individual.
And culture is a two way street.
(05:35):
It's the employee and it's the company.
And we've negated the individual completelyfrom that.
We've kind of said, hey.
We're a best place to work or we're mimickingof the best place to work.
And if you don't work out here, well, thenthat's on you.
And that's a scarlet letter that some peoplehave really had to work hard to overcome when,
in fact, the company itself may not haveorganized itself the right way, and there might
(05:57):
have been a little bit of bait and switch.
Because how many times have you gone to a jobinterview and had the hiring manager say, this
is a terrible place to work.
We have an awful culture.
No.
Every single company has an amazing culture.
Right?
But do they for you?
Is it the right culture for you?
The individual also bears some bonus.
They've gotta know a little bit too aboutthemselves.
Like, where do they like to work?
What are the attributes that matter to them?
When those two things align, when your way ofdoing and the company's way of doing and that's
(06:19):
everything from philosophical beliefs to howyou actually just work.
When those things are in the same box, the samesquare and, you know, same degree of relation,
you've got great culture.
And when those things don't work, when you'reoutside the box, well, then you've got a tough
place to work.
Then you don't really have maybe somethingthat's as interesting.
And so this square that, as I call it, that'sactually definable.
(06:41):
That's that's knowable.
And a lot of people think of culture as thisamorphous way of being.
Think a Harvard professor coined that term, butI actually challenge that.
It is knowable.
And so the book actually tries to frame how youcan construct this in a way that you can
actually do better at organizing your business.
Yes, that sounds amazing.
I witnessed the same.
When you join a company, it's always like it isgiven and you cannot change it.
(07:06):
So you have to accept the culture or thesometimes it's as you said it is also pretended
like it is there but it isn't.
It sounds differently between the employees aswell.
So this is a new system and also like a blackbox.
I mean in the past you think you cannot grab itand you made it, you said applicable or
(07:32):
workable.
Right, it is unknown in many ways.
It's known at an arm's length.
They're only known of what you can see online,and sometimes those glass door reviews are only
the minority perspective.
Sometimes you just get the fluff from HR ashiring managers that, of course, tell you
everything's great.
What if we could do better with that?
And the concept that I'd like to put togetherand really bring forward is something called
(07:55):
constrained independence.
And what is that?
And why does it matter in light oforganizational culture?
Constrained independence is, in short, theknown and communicated degree to which an
employee can action their own ideas.
And if you think about how businesses work orhow anyone works, you, Caroline, you have if
(08:15):
you went to a new job, theoretically, you havea endless universe of decisions you have to
make every day around how to do your job.
If if you had no constraint, you wereunconstrained, you could do anything.
And of course, that would be chaos because ifthere's every employee doing what you're doing,
then there's just no structure.
In order to meet a degree of product qualityservice standard compliance, companies enforce
(08:38):
constraint.
Right?
They constrain that independence.
And and that's not so widely bound that it'suniform into only one thing.
Right?
You have this box.
And that way of doing is that amorphous way ofdoing is kind of what everyone calls culture.
People kind of figure it out about what you doand who does it and does it and how.
Well, the whole point is constraint can vary.
Some people like a very small box or what Iwould call a heavy degree of constraint.
(09:02):
They're more order takers.
They wanna execute.
They don't wanna make decisions.
They just wanna follow.
They're great with that.
Other people, they want a light level ofconstraint.
They want to be able to ideate.
They want to be able to make their owndecisions.
Don't tell I'll figure out how to do it theright way.
Don't worry about me.
And you cannot put the end of the spectrum inin the other scenario because they would
suffocate.
They either would feel like they're tooconstrained or they can't they're constrained
(09:24):
by choice.
Some people just don't wanna make thosechoices.
So you gotta so it goes both ways.
Individuals have to know and companies have toknow.
The point of the Square Management System ishow do you make up that constraint?
Right?
What are the elements?
And there's four sides to the box, and there's10 elements to each side.
And as an executive, if you frame the view fromfrom that that view, the executive view, you
(09:45):
can take those elements.
And in the book, the culture of alignment,which you can find on my website,
townsquare-advisers.com, you can find thesurvey and actually learn all the 40 elements.
You can pick and, and understand and readabout, well, a light level constraint or a high
level constraint and what you would do toaffect that level of constraint for each
element.
This will give you a framework of how toeffectively organize and run your company.
(10:08):
So if you're a startup founder and you got agreat tech idea, but you don't understand how
to build a company, you need to know theseelements.
If you have high if you have retention problemsor you're just not growing, you're not scaling
and you're an executive, take the survey.
Have your staff fill it out.
Have all levels of management fill it out andthen aggregate the scores.
You will figure out the differences of eachside and you'll know exactly where you have a
(10:28):
problem with your organizational structure.
Yes, what a great answer.
I read about this.
You have, you call it test or quiz or so youcan do this on the website.
Of course I put the links in the show notes andI have another question for you.
Sure.
You've worked across private equity investmentbanking and professional sports.
(10:50):
What common cultural misalignments have youseen, and how do they impact performance?
Cultural misalignment?
It's simple.
There's one consistent theme, and it's and it'scommon.
And and now that I've written the book and Ican go back and look at things, I can see where
it where it happens.
The very simple answer is the incomplete squarethe sense that companies don't really know all
(11:12):
the elements that affect culture.
And in conjunction with the incomplete squareis an inability to either to adhere to that
where they don't have the constitution tomaintain the rigidity that it requires.
And so they deviate and that causes tons ofproblems.
And so let me give an example.
What are the four sides?
Right.
The four sides of the square.
The first one is identity.
And that's that's where you start.
(11:34):
That's your mission, your vision, your brandequity.
That is who we are.
And the key question there you wanna ask is, doour employees, do our customers know what we
stand for and why?
And and I think that that is is a helpfulquestion to ask because you you do need to
understand that because you can go what'scalled off strategy.
(11:54):
All of a sudden, you've bought something, youyou've designed something, and people are like,
what are you what are you doing?
We we thought you did business to this.
Why are you over here?
So that's that one.
The second one is instruction.
That is the clarity and consistency ofexpectations.
The key question there, are roles, processesclear and scalable?
The third side is intercommunication.
That's the aforementioned, you know, happy hourand ping pong table.
(12:16):
It's everyone thinks culture is.
It's just one side of the square.
It's how people interact.
It's your use of communication tools, yourtone, meeting cadence.
That that one is really the key question.
Is information flowing in a way that drivesclarity?
And the last one is information feedback.
Are we learning and adapting fast enough?
This is our use of performance measurementsboth from the individual side, performance
trees, and the customer.
(12:37):
They're the the company.
They have to know themselves how they're beingrated.
Those are the four sides.
10 mil 10 elements to each, and they can beinstituted in varying degrees.
It has to work for you, for your company.
It's not about copying somebody else.
That's the key thing.
It's about implementing it for you and adheringto it.
So how does it go awry?
You have an incomplete square.
You don't actually have all the components in,and then people have that means that employees
(12:58):
are left to figure it out themselves.
They put their own square up together, and thatcauses thiefdoms or what I call mini squares
where a department may have different standardsthan another one, and then you get people all
upset at each other because there's varyingdegrees of performance.
The other one is you might have a standard.
You don't adhere to it.
And so this often happens with salespeople.
We have a high performing salesperson, butthey're a terrible actor.
(13:20):
They cause all kinds of problems, but no onewants to let that person go because they're
afraid of the revenue loss.
Well, you're causing more revenue loss andproblems by virtue of keeping that person.
You should stay to your standards and keep thepeople that are inside that box and be okay
with letting them go.
And that's kind of the point.
You gotta have alignment.
You can't have people all over the place.
And so those are the two big things.
Wow.
That's amazing.
(13:40):
Thank you so much for sharing.
Okay.
The key points or what I got from your answeris self awareness.
Why are we doing this and what are we doingactually?
And then when you talk about the elements, Ithought about the completeness of the squares
or we have all the squares together.
(14:01):
Then I thought about the periodic table it'scalled, right, in chemistry.
That you have all the elements how the earth isbuilt but you need them all.
That's right.
You need all the elements in order to makethings, to make them work, to have their
desired outcome.
Right?
And when you when you, when you destabilize theelements, Environmental change, you cause
(14:23):
problems.
And so, you know, that's that's why the squarematters.
It's not binary.
Right?
It is a box.
People you're never gonna have full rigidity.
Now there are places like manufacturing orbiopharma or health care where you have to
have, like, a binary answer because people die.
Right?
Or you have to meet some level of productquality alignment for the most part.
This is a box.
And so the reason it's a box is because you gotto be able to bounce around it.
(14:45):
Why is that so important?
When you are inside the box and you know,everyone else is inside the box, then you trust
each other with a degree of decision making.
You know the borders.
You know what decisions you can make and whatyou can't.
You don't have to ask questions all theCaroline, can I do this?
Caroline, can I do this?
You know the decision that has to get made.
You get to make your own decisions.
That makes you a more interested person in thecompany because you can affect the outcome.
(15:08):
So as a result, you're a happier employeebecause you're like, look.
I made these decisions.
I'm impacting the growth of this business.
So you become a more loyal and trustingemployee, and that leads to continuity.
And we all know it costs more to hire someoneand train someone than it does to keep an
employee on.
Right?
And so when you have trust and you have loyaltyand you feel like you're part of the outcome,
then you are a faster moving employee.
(15:30):
That's how you're gonna get scale.
That's how you're gonna get margin.
That's how you're gonna become more efficient,and people forget that all the time.
So it is people are the most important thing,but you gotta have the systems that around them
to allow for scale to happen because that's thebiggest what I see across all the companies
I've talked to that I've been part of on the mand a side or helped build myself.
If you don't have the systems in place tosupport scale, doesn't matter how great your
(15:50):
employees are, they will never get there.
Yes, that's so true.
Thank you for reminding us.
So you built the system.
I understand and as a team or as an employee Ifeel more that it is important that it matters.
My role matters and everyone knows what I cando and what I cannot do.
(16:12):
It's one part, I think.
That's exactly right.
You know, there is technically, according tothe book, no optimal square.
Right?
There is no the the what matters is whatmatters for the company.
You have the executives who put together thisthe optimal square.
And you as a person, you have your square.
I did ask a hi, though.
I said, hey.
Take the survey.
What is the optimal square for output?
And they they had an interesting answer.
(16:33):
It's not uniform, so it's not all sides oreven.
So if you if you like heavy level ofconstraint, you don't have they they said,
don't put heavy level of constraint on sides.
And their answer was actually have a moderatein identity to allow for you to evolve as a
business, to change to market demands, to givepeople the ability to understand why you've
made strategic changes, but have a heavy,degree of instruction constraint so that
(16:54):
everyone knows what they're doing and why.
That's where a lot of things go awry.
Have a loose level of intercommunicationbecause you wanna have free dialogue across the
organization and then have a moderate degree ofinformation feedback.
And the reason for that was you wanna beanalytical.
You wanna have the understanding of how you'readhering to everything you said you would do,
(17:15):
but you don't wanna have that analysisparalysis where you're actually so stuck in the
weeds that you can't can't move forward.
So that was AI's answer.
I think that if you were an individuallistening or if you're an executive listening,
you can take a free quiz online attownsquare-advisors.com.
You can even go a step further into the actualelements of the Square system.
(17:35):
So you can do a free quiz, or you can do youpay to get access to the full 40 process and
really dig and learn more.
Most everyone who takes it will tell you that,yeah, it sounds right, but they were probably a
little more curious about their preferredworking environment than they thought.
I think it will pull out some interestingresults about your preferred way of doing it
when you take the quiz.
Oh, I love it.
Thank you so much.
(17:55):
Yeah.
Also for all your shares and insights.
Of course, I have a new, next question for you.
In a world obsessed with growth and speed, howdo you convince leaders that alignment and
trust are worth the investment?
Really, really good question.
And the answer is, honestly, I think you haveto have a philosophical belief that this is the
(18:19):
right way to to to run a company.
You know, at the book I'm working on, theculture of alignment, which is written but not
published.
I'm working on that.
Get it yourself an advanced copy.
You can do that online attownsquare-advisors.com.
But the the the point of the book is toactually showcase, like, how do we get we got
it wrong.
Fifty percent of new hires actually quit in thefirst eighteen months.
(18:40):
So this common sized approach that we've takento hiring, to organizational design, to policy,
it isn't working.
And it's because we just said this is the bestplace to work.
We went so broad.
You gotta sit down and really know who you areas a company.
I And think intuitively, would make sense to alot of people, but you really know, a lot of
people haven't thought that way.
So this is a challenge to what corporateculture is.
(19:01):
Yes.
Speed matters.
Scale matters.
Growth matters.
But if you really took a look at your ownbusiness and how you're scaling and how you're
growing, something tells you most companiesprobably aren't doing it the best way, and they
probably have churn issues.
A lot of high scale, growing businesses haveretention problems, and it's because they
didn't scale the right way.
And so I I would argue that the the the thisisn't hard to implement.
(19:23):
It's minor augmentations of your own systemsand processes.
In fact, the book is more I call it a pocketguide because it's designed to be used.
It's short.
You wanna you go take the quiz online rightnow, and you can start actioning it
immediately.
And you should really take the quiz and andthen figure out exactly where the changes you
need to make in your business.
And it's a couple little changes in the andknowing what a complete square is not hard to
put together, if you operate a company.
(19:46):
I love it.
Thank you so much.
Okay.
I learned something, and it is because you saidit's easy to implement and it is like also not
one system for all.
You said about the copy, don't copy others.
You have to find your own way as well and wecan do this with your book.
Thank you so much.
(20:07):
Or your method because the book is about themethod.
It's not about reading.
It's about implementing, of course.
And companies are dynamic.
Yes.
Yeah.
Exactly.
I'm not what I'm not doing is trying toconvince you, you know, and I even joke about
it in the book.
I don't have an army of grad students churningout research.
Right?
Because I do think that's the error that a lotof business folks make.
(20:30):
They I have some of my in my office behind me,and they've aggregated information.
They said, hey.
These this is what these people did.
You should do that.
And there's a degree to which listen, Iunderstand why that makes sense.
Right?
You know, this is what success looks like.
At the same time, that doesn't mean that it'ssuccess for you.
And so I think people need to deep dive intotheir own personal partialities about their
(20:51):
working environments where they found success.
And I think companies need to understand whatsuccess looks like in their organization and
actually stick to it.
The point is you do this at a survey, a 40survey at the executive level, senior, middle,
and frontline, and you can very quickly see asa diagnostic tool where your company is
misaligned.
Moreover, you can take the quiz and look at itand say, this is where we are now, and then
(21:14):
take it again and look at was where I want tobe.
And you'll understand the elements you need tochange.
And so you don't really need to change yourwhole business.
You might need to just change some of yourbusinesses.
And again, each area of the square has reallycommon points of failure.
So on the identity identity side, it's offstrategy, which is mission to product drift.
And so companies go off offline because they'vedecided to do something that doesn't map quite
(21:38):
to what their ideal profile is or at least whatthey've told the public, and then everyone gets
confused.
And I've seen that a few times.
On the instruction side, people don't onboardfully or correctly or in the right way.
And so there's, you know, the default Imentioned before.
Employees are left to figuring it outthemselves, and then they set their own
standards, and then you've got problems.
On the intercommunication, it's usuallymessaging not flowing from the executive to the
(21:59):
frontline properly.
So you gotta set those systems correctly, andthat can cause a significant amount of problem.
And then and then then on the, informationfeedback, the last one, everyone is good at
people reviews.
Companies are bad at their own reviews.
They like to think they're great.
And so companies have to listen better to thefeedback they're getting from their staff and
from the public and do better with that.
(22:20):
And that's where companies usually go arise attheir own feedback.
Yes, that's so true.
Thank you for mentioning.
So we have to be honest with ourselves and forexample you call it executives, right?
When you are a decision maker or you haveresponsibility, honesty, like looking at self
(22:42):
awareness, we talked about this, right?
Exactly.
So I have one last question for you and I'm sohappy that we did this interview and I learned
something.
It's about your goals.
I know you have your book as one of your nextprojects.
Do you set goals for yourself or intentions?
Oh sure.
(23:02):
Right now is is really publicizing andpromoting the thought leadership behind this
and and getting people to learn more about thesystem and action it and get the book
published.
So looking at advanced promotion right now, goto townsquare-advisors.com.
You could take the free quiz, which is muchshorter.
It's only 10 questions.
Should be easy, but you can do that as anindividual or from the perspective as a as a
(23:23):
corporate executive.
But if you wanna dig in, go take the four full40 survey on the Square management system.
It's gonna deep dive into all the elements, allthe sides.
You'll get a score.
You'll know a little bit more about yourself.
I think it's a great diagnostic tool, but it'salso a great self assessment tool.
People love doing it because they find itinteresting.
It's very simple.
It's easy to do.
I know 40 points sounds long, but it's not.
(23:44):
And, hopefully, through that, we'll get somewe'll get the book out there and, and get more
people really improving their business, bothemployees and and and executives, as a way to
engage and create better corporate health.
I think that's my goal long term, is to getcompanies operating in a better way and
changing how they think about operations in away that affects culture more than maybe they
probably realize.
Oh, I love it.
(24:05):
Thank you so much.
Yes, please reach out to Matthew.
He's amazing.
He shares his knowledge and wisdom with us andalso the test, the quiz.
It sounds like it is playful, right?
It's a lot of fun as well and then we haveresults.
Thank you so much again and now it's time foryour final thoughts to the audience, please.
(24:26):
The final thought to the audience is reallysimple.
Have the constitution to stick to who you areas a person and not chameleon yourself into
some level of common size or commoditizedcorporate culture.
Take in in for executives, stop copying.
You gotta step back and work with who you areand what you want and be honest with yourself
(24:50):
about that.
And we've stepped away from that, in culturethese days.
And there's a lot of reasons for why that'shappened.
But but let's get back to putting yourself inthe right place to be.
You'll be a happier, better, more productiveemployee.
And and, you know, everyone knows work lifebalance matters.
If you're if you're on if you're not happy inwork, you're not happy in life at times, let's
fix that.
And let's have companies, whole companies tothe same level of standard.
(25:11):
Let's do better for our employees rather thanjust offering free coffee and snacks.
Right?
There's more to it than So both sides need toget better at understanding how they work.
And when we do, we're gonna have betteremployees and better companies.
Wow.
I love it.
Thank you so much.
Thanks for having me.
It's been a pleasure.
And I see you in the next episode.
(25:32):
Thank you for listening to Inspire Choicetoday.
I'm thrilled to have you on this journey ofgrowth and transformation.
Don't forget to hit follow or subscribe to stayconnected and never miss an episode.
And here's something special.
Grab your free twenty minute breakthroughsession with me.
It's designed to help you kick start or levelup your business.
(25:55):
Just check out the show notes for more.
Until next time, keep making those inspiredchoices.
See you in the next episode.
And so I think people need to deep dive intotheir own personal partialities about their
(00:05):
working environments where they found success.
And I think companies need to understand whatsuccess looks like in their organization and
actually stick to it.
The the point is you you do this at a survey,the 40 survey at the executive level, senior,
middle, and frontline, and you can very quicklysee as a diagnostic tool where your company is
misaligned.
Moreover, you can take the quiz and look at itand say, this is where we are now.
(00:29):
And then take it again and look at, this iswhere I wanna be.
And you'll understand the elements you need tochange.
Welcome to Inspire Choice today.
I'm your host, Caroline Biseltzky, here tobring you authentic stories, surprising
lessons, and powerful takeaways to fuel yourjourney in business and life.
In each episode, I'll take you from oneinspiring guest to the next, blending their
(00:52):
experiences with my expertise to uncoverpractical strategies you can use right away.
Whether you're starting out or stepping up,stay tuned for insights and actionable tips
that make a difference.
And stick around until the end for a specialfreebie just for our listeners.
(01:13):
Hello and welcome inspired podcast community.
This is your new episode.
My name is Caroline and my today's guest isMatthew Pearson.
I'm so happy that he said yes to our interview.
How are you doing today?
I'm great.
Thanks for having me.
Really appreciate it.
Thank you so much and I would like to introduceyou to the audience.
(01:36):
Of course, you are a seasoned executive withover two decades of experience in M and A.
That stands for merger and acquisition, right?
Yeah, a cross between M and A and executiveexperience as well.
And then strategy and high level leadership.
You are the creator of the Square ManagementSystem and author of the upcoming book The
(01:59):
Culture of Alignment where you explore howtrust and structure can transform company
culture.
Welcome to the inspired podcast Wow!
Matthew Pearson.
Thank you for having me.
Pleasure.
That's so great.
My first question for you is, what inspired youto develop the Square management system?
(02:20):
And how does it redefine traditional leadershipframeworks?
It's a great question.
This is something that I was pushed into.
And so in many ways, I'm a fitting guest foryour, podcast.
When I answered an interview question maybeeight or nine years ago, I was asked, how would
(02:40):
you affect organizational culture and alignmentacross, you know, six, seven hundred employees
who were in four offices in three states?
And my answer was the beginning of what becamethe Square management system.
If only because the recruiter said it was themost unique answer that had ever been given to
that question, and then I should probably dosomething with my logic.
(03:02):
And to me, the logic stemmed from my experiencemanaging professional sports franchises and
array of people in disparate roles.
And, you know, that was just how I approachedit over the years.
Would mention it to people and they would kindof say the same thing.
That's in that makes sense, but you should dosomething with that.
That's interesting and I needed to develop it.
(03:23):
And so I pinged people along the way.
I pinged other offers.
I pinged executives.
I pinged publishers.
Does this make sense?
Would anyone like to learn more about this?
Is this actionable?
And I got advice from a lot of people along theway, and they pushed me to continue to develop
it.
And it took a long time, in part because I hadother obligations, but in part because I needed
to think through it.
(03:44):
As I saw my different life experiences from acareer professional experience, come forward, I
saw the applicability become more and morereal, and it refined a lot of the way I thought
about it.
And I finally actually had enough cumulativeexperience to put it all together in a more
actionable framework, and I finally wrote thebook.
But I needed that time to go from idea tostructure in order to to get to where I am
(04:09):
today.
And so I had inspiration from a lot of peoplewho enjoyed what I was talking about and help
test and and kind of reframe the way I wasapproaching it.
Oh, I love your answer.
Thank you so much for explaining to us.
It sounds like you did a little customerdiscovery at the beginning to see, how they
like it Or
(04:30):
I did.
Well, I did some I did some discovery, and Iused it, and I applied it.
And I knew it would work based on my priorexperience, but it needed it needed rigor, and
it needed adjustment.
And so and then, of course, the act of writing,it helps refine things.
Then you have to really make it actual,digestible, understandable.
And so it it it kind of morphed over time as II put it together to something that maybe was a
(04:53):
little bit more of a complete package.
You know, why does this work?
In of in short, you know, the problem withorganizational culture right now is it's common
sized, and it's also one directional, which isreally the company perspective.
And a lot of companies say, hey.
We're gonna go look at the best places to work.
In in a lot of business books, they just teachyou to copy.
(05:14):
I I interviewed a thousand companies.
I talked to 800 CEOs, and these are theaggregate things that we learned about those
collective groups of people.
We've kind of averaged it out and said, youshould if wanna be like them, you should do
these things.
Well, copying someone else's work doesn't meanthat it works for you.
And then also, and from an organizationalperspective, it negates the input of the
individual.
And culture is a two way street.
(05:35):
It's the employee and it's the company.
And we've negated the individual completelyfrom that.
We've kind of said, hey.
We're a best place to work or we're mimickingof the best place to work.
And if you don't work out here, well, thenthat's on you.
And that's a scarlet letter that some peoplehave really had to work hard to overcome when,
in fact, the company itself may not haveorganized itself the right way, and there might
(05:57):
have been a little bit of bait and switch.
Because how many times have you gone to a jobinterview and had the hiring manager say, this
is a terrible place to work.
We have an awful culture.
No.
Every single company has an amazing culture.
Right?
But do they for you?
Is it the right culture for you?
The individual also bears some bonus.
They've gotta know a little bit too aboutthemselves.
Like, where do they like to work?
What are the attributes that matter to them?
When those two things align, when your way ofdoing and the company's way of doing and that's
(06:19):
everything from philosophical beliefs to howyou actually just work.
When those things are in the same box, the samesquare and, you know, same degree of relation,
you've got great culture.
And when those things don't work, when you'reoutside the box, well, then you've got a tough
place to work.
Then you don't really have maybe somethingthat's as interesting.
And so this square that, as I call it, that'sactually definable.
(06:41):
That's that's knowable.
And a lot of people think of culture as thisamorphous way of being.
Think a Harvard professor coined that term, butI actually challenge that.
It is knowable.
And so the book actually tries to frame how youcan construct this in a way that you can
actually do better at organizing your business.
Yes, that sounds amazing.
I witnessed the same.
When you join a company, it's always like it isgiven and you cannot change it.
(07:06):
So you have to accept the culture or thesometimes it's as you said it is also pretended
like it is there but it isn't.
It sounds differently between the employees aswell.
So this is a new system and also like a blackbox.
I mean in the past you think you cannot grab itand you made it, you said applicable or
(07:32):
workable.
Right, it is unknown in many ways.
It's known at an arm's length.
They're only known of what you can see online,and sometimes those glass door reviews are only
the minority perspective.
Sometimes you just get the fluff from HR ashiring managers that, of course, tell you
everything's great.
What if we could do better with that?
And the concept that I'd like to put togetherand really bring forward is something called
(07:55):
constrained independence.
And what is that?
And why does it matter in light oforganizational culture?
Constrained independence is, in short, theknown and communicated degree to which an
employee can action their own ideas.
And if you think about how businesses work orhow anyone works, you, Caroline, you have if
(08:15):
you went to a new job, theoretically, you havea endless universe of decisions you have to
make every day around how to do your job.
If if you had no constraint, you wereunconstrained, you could do anything.
And of course, that would be chaos because ifthere's every employee doing what you're doing,
then there's just no structure.
In order to meet a degree of product qualityservice standard compliance, companies enforce
(08:38):
constraint.
Right?
They constrain that independence.
And and that's not so widely bound that it'suniform into only one thing.
Right?
You have this box.
And that way of doing is that amorphous way ofdoing is kind of what everyone calls culture.
People kind of figure it out about what you doand who does it and does it and how.
Well, the whole point is constraint can vary.
Some people like a very small box or what Iwould call a heavy degree of constraint.
(09:02):
They're more order takers.
They wanna execute.
They don't wanna make decisions.
They just wanna follow.
They're great with that.
Other people, they want a light level ofconstraint.
They want to be able to ideate.
They want to be able to make their owndecisions.
Don't tell I'll figure out how to do it theright way.
Don't worry about me.
And you cannot put the end of the spectrum inin the other scenario because they would
suffocate.
They either would feel like they're tooconstrained or they can't they're constrained
(09:24):
by choice.
Some people just don't wanna make thosechoices.
So you gotta so it goes both ways.
Individuals have to know and companies have toknow.
The point of the Square Management System ishow do you make up that constraint?
Right?
What are the elements?
And there's four sides to the box, and there's10 elements to each side.
And as an executive, if you frame the view fromfrom that that view, the executive view, you
(09:45):
can take those elements.
And in the book, the culture of alignment,which you can find on my website,
townsquare-advisers.com, you can find thesurvey and actually learn all the 40 elements.
You can pick and, and understand and readabout, well, a light level constraint or a high
level constraint and what you would do toaffect that level of constraint for each
element.
This will give you a framework of how toeffectively organize and run your company.
(10:08):
So if you're a startup founder and you got agreat tech idea, but you don't understand how
to build a company, you need to know theseelements.
If you have high if you have retention problemsor you're just not growing, you're not scaling
and you're an executive, take the survey.
Have your staff fill it out.
Have all levels of management fill it out andthen aggregate the scores.
You will figure out the differences of eachside and you'll know exactly where you have a
(10:28):
problem with your organizational structure.
Yes, what a great answer.
I read about this.
You have, you call it test or quiz or so youcan do this on the website.
Of course I put the links in the show notes andI have another question for you.
Sure.
You've worked across private equity investmentbanking and professional sports.
(10:50):
What common cultural misalignments have youseen, and how do they impact performance?
Cultural misalignment?
It's simple.
There's one consistent theme, and it's and it'scommon.
And and now that I've written the book and Ican go back and look at things, I can see where
it where it happens.
The very simple answer is the incomplete squarethe sense that companies don't really know all
(11:12):
the elements that affect culture.
And in conjunction with the incomplete squareis an inability to either to adhere to that
where they don't have the constitution tomaintain the rigidity that it requires.
And so they deviate and that causes tons ofproblems.
And so let me give an example.
What are the four sides?
Right.
The four sides of the square.
The first one is identity.
And that's that's where you start.
(11:34):
That's your mission, your vision, your brandequity.
That is who we are.
And the key question there you wanna ask is, doour employees, do our customers know what we
stand for and why?
And and I think that that is is a helpfulquestion to ask because you you do need to
understand that because you can go what'scalled off strategy.
(11:54):
All of a sudden, you've bought something, youyou've designed something, and people are like,
what are you what are you doing?
We we thought you did business to this.
Why are you over here?
So that's that one.
The second one is instruction.
That is the clarity and consistency ofexpectations.
The key question there, are roles, processesclear and scalable?
The third side is intercommunication.
That's the aforementioned, you know, happy hourand ping pong table.
(12:16):
It's everyone thinks culture is.
It's just one side of the square.
It's how people interact.
It's your use of communication tools, yourtone, meeting cadence.
That that one is really the key question.
Is information flowing in a way that drivesclarity?
And the last one is information feedback.
Are we learning and adapting fast enough?
This is our use of performance measurementsboth from the individual side, performance
trees, and the customer.
(12:37):
They're the the company.
They have to know themselves how they're beingrated.
Those are the four sides.
10 mil 10 elements to each, and they can beinstituted in varying degrees.
It has to work for you, for your company.
It's not about copying somebody else.
That's the key thing.
It's about implementing it for you and adheringto it.
So how does it go awry?
You have an incomplete square.
You don't actually have all the components in,and then people have that means that employees
(12:58):
are left to figure it out themselves.
They put their own square up together, and thatcauses thiefdoms or what I call mini squares
where a department may have different standardsthan another one, and then you get people all
upset at each other because there's varyingdegrees of performance.
The other one is you might have a standard.
You don't adhere to it.
And so this often happens with salespeople.
We have a high performing salesperson, butthey're a terrible actor.
(13:20):
They cause all kinds of problems, but no onewants to let that person go because they're
afraid of the revenue loss.
Well, you're causing more revenue loss andproblems by virtue of keeping that person.
You should stay to your standards and keep thepeople that are inside that box and be okay
with letting them go.
And that's kind of the point.
You gotta have alignment.
You can't have people all over the place.
And so those are the two big things.
Wow.
That's amazing.
(13:40):
Thank you so much for sharing.
Okay.
The key points or what I got from your answeris self awareness.
Why are we doing this and what are we doingactually?
And then when you talk about the elements, Ithought about the completeness of the squares
or we have all the squares together.
(14:01):
Then I thought about the periodic table it'scalled, right, in chemistry.
That you have all the elements how the earth isbuilt but you need them all.
That's right.
You need all the elements in order to makethings, to make them work, to have their
desired outcome.
Right?
And when you when you, when you destabilize theelements, Environmental change, you cause
(14:23):
problems.
And so, you know, that's that's why the squarematters.
It's not binary.
Right?
It is a box.
People you're never gonna have full rigidity.
Now there are places like manufacturing orbiopharma or health care where you have to
have, like, a binary answer because people die.
Right?
Or you have to meet some level of productquality alignment for the most part.
This is a box.
And so the reason it's a box is because you gotto be able to bounce around it.
(14:45):
Why is that so important?
When you are inside the box and you know,everyone else is inside the box, then you trust
each other with a degree of decision making.
You know the borders.
You know what decisions you can make and whatyou can't.
You don't have to ask questions all theCaroline, can I do this?
Caroline, can I do this?
You know the decision that has to get made.
You get to make your own decisions.
That makes you a more interested person in thecompany because you can affect the outcome.
(15:08):
So as a result, you're a happier employeebecause you're like, look.
I made these decisions.
I'm impacting the growth of this business.
So you become a more loyal and trustingemployee, and that leads to continuity.
And we all know it costs more to hire someoneand train someone than it does to keep an
employee on.
Right?
And so when you have trust and you have loyaltyand you feel like you're part of the outcome,
then you are a faster moving employee.
(15:30):
That's how you're gonna get scale.
That's how you're gonna get margin.
That's how you're gonna become more efficient,and people forget that all the time.
So it is people are the most important thing,but you gotta have the systems that around them
to allow for scale to happen because that's thebiggest what I see across all the companies
I've talked to that I've been part of on the mand a side or helped build myself.
If you don't have the systems in place tosupport scale, doesn't matter how great your
(15:50):
employees are, they will never get there.
Yes, that's so true.
Thank you for reminding us.
So you built the system.
I understand and as a team or as an employee Ifeel more that it is important that it matters.
My role matters and everyone knows what I cando and what I cannot do.
(16:12):
It's one part, I think.
That's exactly right.
You know, there is technically, according tothe book, no optimal square.
Right?
There is no the the what matters is whatmatters for the company.
You have the executives who put together thisthe optimal square.
And you as a person, you have your square.
I did ask a hi, though.
I said, hey.
Take the survey.
What is the optimal square for output?
And they they had an interesting answer.
(16:33):
It's not uniform, so it's not all sides oreven.
So if you if you like heavy level ofconstraint, you don't have they they said,
don't put heavy level of constraint on sides.
And their answer was actually have a moderatein identity to allow for you to evolve as a
business, to change to market demands, to givepeople the ability to understand why you've
made strategic changes, but have a heavy,degree of instruction constraint so that
(16:54):
everyone knows what they're doing and why.
That's where a lot of things go awry.
Have a loose level of intercommunicationbecause you wanna have free dialogue across the
organization and then have a moderate degree ofinformation feedback.
And the reason for that was you wanna beanalytical.
You wanna have the understanding of how you'readhering to everything you said you would do,
(17:15):
but you don't wanna have that analysisparalysis where you're actually so stuck in the
weeds that you can't can't move forward.
So that was AI's answer.
I think that if you were an individuallistening or if you're an executive listening,
you can take a free quiz online attownsquare-advisors.com.
You can even go a step further into the actualelements of the Square system.
(17:35):
So you can do a free quiz, or you can do youpay to get access to the full 40 process and
really dig and learn more.
Most everyone who takes it will tell you that,yeah, it sounds right, but they were probably a
little more curious about their preferredworking environment than they thought.
I think it will pull out some interestingresults about your preferred way of doing it
when you take the quiz.
Oh, I love it.
Thank you so much.
(17:55):
Yeah.
Also for all your shares and insights.
Of course, I have a new, next question for you.
In a world obsessed with growth and speed, howdo you convince leaders that alignment and
trust are worth the investment?
Really, really good question.
And the answer is, honestly, I think you haveto have a philosophical belief that this is the
(18:19):
right way to to to run a company.
You know, at the book I'm working on, theculture of alignment, which is written but not
published.
I'm working on that.
Get it yourself an advanced copy.
You can do that online attownsquare-advisors.com.
But the the the point of the book is toactually showcase, like, how do we get we got
it wrong.
Fifty percent of new hires actually quit in thefirst eighteen months.
(18:40):
So this common sized approach that we've takento hiring, to organizational design, to policy,
it isn't working.
And it's because we just said this is the bestplace to work.
We went so broad.
You gotta sit down and really know who you areas a company.
I And think intuitively, would make sense to alot of people, but you really know, a lot of
people haven't thought that way.
So this is a challenge to what corporateculture is.
(19:01):
Yes.
Speed matters.
Scale matters.
Growth matters.
But if you really took a look at your ownbusiness and how you're scaling and how you're
growing, something tells you most companiesprobably aren't doing it the best way, and they
probably have churn issues.
A lot of high scale, growing businesses haveretention problems, and it's because they
didn't scale the right way.
And so I I would argue that the the the thisisn't hard to implement.
(19:23):
It's minor augmentations of your own systemsand processes.
In fact, the book is more I call it a pocketguide because it's designed to be used.
It's short.
You wanna you go take the quiz online rightnow, and you can start actioning it
immediately.
And you should really take the quiz and andthen figure out exactly where the changes you
need to make in your business.
And it's a couple little changes in the andknowing what a complete square is not hard to
put together, if you operate a company.
(19:46):
I love it.
Thank you so much.
Okay.
I learned something, and it is because you saidit's easy to implement and it is like also not
one system for all.
You said about the copy, don't copy others.
You have to find your own way as well and wecan do this with your book.
Thank you so much.
(20:07):
Or your method because the book is about themethod.
It's not about reading.
It's about implementing, of course.
And companies are dynamic.
Yes.
Yeah.
Exactly.
I'm not what I'm not doing is trying toconvince you, you know, and I even joke about
it in the book.
I don't have an army of grad students churningout research.
Right?
Because I do think that's the error that a lotof business folks make.
(20:30):
They I have some of my in my office behind me,and they've aggregated information.
They said, hey.
These this is what these people did.
You should do that.
And there's a degree to which listen, Iunderstand why that makes sense.
Right?
You know, this is what success looks like.
At the same time, that doesn't mean that it'ssuccess for you.
And so I think people need to deep dive intotheir own personal partialities about their
(20:51):
working environments where they found success.
And I think companies need to understand whatsuccess looks like in their organization and
actually stick to it.
The point is you do this at a survey, a 40survey at the executive level, senior, middle,
and frontline, and you can very quickly see asa diagnostic tool where your company is
misaligned.
Moreover, you can take the quiz and look at itand say, this is where we are now, and then
(21:14):
take it again and look at was where I want tobe.
And you'll understand the elements you need tochange.
And so you don't really need to change yourwhole business.
You might need to just change some of yourbusinesses.
And again, each area of the square has reallycommon points of failure.
So on the identity identity side, it's offstrategy, which is mission to product drift.
And so companies go off offline because they'vedecided to do something that doesn't map quite
(21:38):
to what their ideal profile is or at least whatthey've told the public, and then everyone gets
confused.
And I've seen that a few times.
On the instruction side, people don't onboardfully or correctly or in the right way.
And so there's, you know, the default Imentioned before.
Employees are left to figuring it outthemselves, and then they set their own
standards, and then you've got problems.
On the intercommunication, it's usuallymessaging not flowing from the executive to the
(21:59):
frontline properly.
So you gotta set those systems correctly, andthat can cause a significant amount of problem.
And then and then then on the, informationfeedback, the last one, everyone is good at
people reviews.
Companies are bad at their own reviews.
They like to think they're great.
And so companies have to listen better to thefeedback they're getting from their staff and
from the public and do better with that.
(22:20):
And that's where companies usually go arise attheir own feedback.
Yes, that's so true.
Thank you for mentioning.
So we have to be honest with ourselves and forexample you call it executives, right?
When you are a decision maker or you haveresponsibility, honesty, like looking at self
(22:42):
awareness, we talked about this, right?
Exactly.
So I have one last question for you and I'm sohappy that we did this interview and I learned
something.
It's about your goals.
I know you have your book as one of your nextprojects.
Do you set goals for yourself or intentions?
Oh sure.
(23:02):
Right now is is really publicizing andpromoting the thought leadership behind this
and and getting people to learn more about thesystem and action it and get the book
published.
So looking at advanced promotion right now, goto townsquare-advisors.com.
You could take the free quiz, which is muchshorter.
It's only 10 questions.
Should be easy, but you can do that as anindividual or from the perspective as a as a
(23:23):
corporate executive.
But if you wanna dig in, go take the four full40 survey on the Square management system.
It's gonna deep dive into all the elements, allthe sides.
You'll get a score.
You'll know a little bit more about yourself.
I think it's a great diagnostic tool, but it'salso a great self assessment tool.
People love doing it because they find itinteresting.
It's very simple.
It's easy to do.
I know 40 points sounds long, but it's not.
(23:44):
And, hopefully, through that, we'll get somewe'll get the book out there and, and get more
people really improving their business, bothemployees and and and executives, as a way to
engage and create better corporate health.
I think that's my goal long term, is to getcompanies operating in a better way and
changing how they think about operations in away that affects culture more than maybe they
probably realize.
Oh, I love it.
(24:05):
Thank you so much.
Yes, please reach out to Matthew.
He's amazing.
He shares his knowledge and wisdom with us andalso the test, the quiz.
It sounds like it is playful, right?
It's a lot of fun as well and then we haveresults.
Thank you so much again and now it's time foryour final thoughts to the audience, please.
(24:26):
The final thought to the audience is reallysimple.
Have the constitution to stick to who you areas a person and not chameleon yourself into
some level of common size or commoditizedcorporate culture.
Take in in for executives, stop copying.
You gotta step back and work with who you areand what you want and be honest with yourself
(24:50):
about that.
And we've stepped away from that, in culturethese days.
And there's a lot of reasons for why that'shappened.
But but let's get back to putting yourself inthe right place to be.
You'll be a happier, better, more productiveemployee.
And and, you know, everyone knows work lifebalance matters.
If you're if you're on if you're not happy inwork, you're not happy in life at times, let's
fix that.
And let's have companies, whole companies tothe same level of standard.
(25:11):
Let's do better for our employees rather thanjust offering free coffee and snacks.
Right?
There's more to it than So both sides need toget better at understanding how they work.
And when we do, we're gonna have betteremployees and better companies.
Wow.
I love it.
Thank you so much.
Thanks for having me.
It's been a pleasure.
And I see you in the next episode.
(25:32):
Thank you for listening to Inspire Choicetoday.
I'm thrilled to have you on this journey ofgrowth and transformation.
Don't forget to hit follow or subscribe to stayconnected and never miss an episode.
And here's something special.
Grab your free twenty minute breakthroughsession with me.
It's designed to help you kick start or levelup your business.
(25:55):
Just check out the show notes for more.
Until next time, keep making those inspiredchoices.
See you in the next episode.
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Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
New Heights with Jason & Travis Kelce
Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!