
Strategic’s EOS Story - Episode 25

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Hello, and welcome to the Life By Design podcast, brought to you by Strategic.
This podcast is all about helping you live your great life.
welcome back to the Life By Design podcast.
I'm very happy to have my next guest today, which is Alan Leese III, our CEO here at Strategic.
And Alan is coming on because since I joined the firm, uh, Alan, the firm, everyone's been focused on this thing called EOS, which is Entrepreneurial Operating System, and it's something that's really been a key to the firm's success.
And so I thought it would be interesting to have Alan on today to discuss why, what is EOS, and- and how it's changed the outlook for the firm.
Well, uh, Jay, as they say in every podcast, I am thrilled to be here.
You do a heck of a job with this, so I appreciate being one of your guests and all the effort that you put into this.
So thank you.
Yeah.
No, thank you for coming on, and, uh, I'm really excited about this.
You know, this is something, uh, as I said in the intro there, you guy- we talk about a lot at the firm, and I've seen it firsthand since I've been here.
And I think our first question that I need to ask for the listeners at home is, w- what is EOS?
So the EOS system is the Entrepreneurial Operating System, as you mentioned, and, uh, what it is is a system.
It's not a software system.
It's just a series of different concepts, different tools that businesses somewhere between, we'll say, 5 and 250 people, but it can be smaller or bigger, uh, use to help run their business better.
And when you think about running the business better, uh, from our standpoint, it is having a really clear vision what you're trying to accomplish, having the discipline to accomplish that, assigning accountability to that process, and then hopefully enjoying the fruits of that labor, uh, as it comes out of the process.
So it has been revolutionary, I believe, for this business- Mm.
and I'm thrilled to share it.
I- I've said several times, uh, in town halls, in EOS reviews, it is gospel, uh, to me.
Uh, I believe that strongly in it and- and very pleased to share some of that information with the group.
Yeah, I think it's great, and so one of the first things, uh, you know, specifically for me but also for the listeners was, what was the challenge in the firm's business that led you to adopt EOS?
Sure.
Sure.
So, uh, when you think back to the- the history of the firm, we- we are, uh, blessed to know that my dad, uh, and Judy built a really successful wealth management and retirement plan business.
And the skill set that it took to do that from 0
So at 1 point, there was one person sitting in an office in Utica, New York, with 0 assets under management.
And the skill set it took to get that from, say, 0 to a billion, um, which is funny to say because it's certainly not that easy, uh, was one that was extremely entrepreneurial.
You had to be great at service.
You had to be great at sales.
You had to be great at leading people, recruiting, so many different skills, but it was very much a entrepreneurial environment where they just had to grind it out and figure out a way to make it work.
Mm.
And as I think about taking over the business, which happened in 2017, from a CEO standpoint, I have said this many times to the people here, which is, we have this gift, this blessing of all that hard stuff being done in advance, but now realizing it takes a different skill set to ensure you protect it and grow it from there.
And that's a move from kinda that entrepreneurial, boots-on-the-ground, um, mindset to one where, let's institutionalize the business so we get the right processes in place, um, whether it's HR, whether it's operations, whether it's investment management.
All the different things that it takes to run a world-class wealth management firm I found in EOS.
So that- that was the, uh, issue or the opportunity I was trying to solve, which is to say, how do we switch the culture from one of entrepreneurial, "Let's just figure it out" and really hope that we make it to say, "Hey, we have a gift here.
Let's protect it and really make it thrive going forward."
And there was a change in skill set there.
Yeah, and so once you kind of looked around, you saw EOS.
You were like, "This- this is what's for us."
Uh, was there a particular moment that convinced you that it- that you made the right decision?
So I'll- I'll recognize a program called Strategic Coach, which is run by a gentleman, uh, named Dan Sullivan.
Many of the listeners may be familiar with him.
Uh, if you're not, look it up.
Uh, the program, uh, is in Toronto, but it's now spread to other parts of the US.
Dan, um, had a class that I went to, and several of our clients, uh- uh, went to as well, that helped, uh, people like me run a business like, uh, Strategic.
And one of my peers in that group said, "Hey man, have- have you ever heard of EOS?"
I said, "Nope."
He goes, "You ever read Traction?"
I said, "Nope."
He said, "It is the best business book I've ever read, and I run my entire business on that."
And I had never heard of it.
This was- this was, geez, probably 8, 9 years ago now.
Um, and I said, "Well, that- that's interesting.
If you s- hear this is the best business book I've ever read from somebody that you respect, maybe you should pick it up."
So that was the moment where I, um, learned about it.
Mm.
And then we'll talk in a minute about kinda the evolution on- on how we implemented it, but that was when the light bulb went off and said, "Hey, I need to figure out a way to really run this business in a systematized way.
Maybe EOS is the solution."
And it turned out to be the case.
Yeah, and I- I think we can go to that.
So- so EOS works on rocks.
They're basically like goals to, like
wash it down to its simplest form.
But how did you introduce the first 90-day rocks for Strategic and, like, what were your priorities going into that?
I really messed that up, so thank you-
thank you for-
thank you for asking.
Uh, as, um, is often the case when you get a bunch of, uh, smart, uh, hardworking people in a room, uh, they think they have the answers, and I was convinced that we could run, uh, the principles of EOS that were found in Traction in the second book, Get a Grip, uh, ourselves.
And so we tried to do that for about a year.
Hmm.
And so part of the, uh, mistakes that we made were, 1, we weren't doing the EOS process as disciplined as we needed to be, and 2, we ended up with about 100 different rocks.
"Boy, we're gonna solve all of these issues," and I call them issues and opportunities, "on day one," and it was chaos.
Okay?
So when you talk about how was it introduced, it was introduced in a really sloppy way.
Fortunately, we took a breath and said, "Wait a second."
"We know this system probably works.
What do we need to do to do it right?"
And we went out and found an imple- implementer named Mark O'Donnell, who now runs EOS, and he came here and set us straight and said, "This is how you do EOS for real," and that was the real kickoff- Mm-hmm.
lightning in a bottle, um, from my standpoint, in terms of being able to transition this business into what it is today and hopefully what it can be, uh, in the future.
So do you feel like, you know, in EOS, it asks leaders to model the way.
Mm-hmm.
So do you feel like, was that your shift from a daily habit or was there another shift for you that you were like, "Oh, this is, this is what's gonna let me model the way"?
Okay.
I wanna, I wanna take a, a step back before I- Yeah.
I answer that question and really explain a few of the core tenets of what makes EOS successful- Hm.
uh, in my book, and then that will, will maybe lead up to, um, how I've tried to model it.
So when you think about EOS, it starts with the VTO, the Vision Traction Organizer, and that is a quarterly strategic plan updated every 3 months to say what is the vision for the business?
What is your purpose?
What are your values?
And, and some of the, the listeners may think that is a, a cliché.
You always hear you have to define your values, you have to define your purpose.
It just happens to be true.
Mm-hmm.
So make sure you do that, and then talk about where do you want this business to go with those 2 core tenets as the foundation?
Where do you want it to be in 10 years?
Where do you want it to be in 3 years?
Where do you want it to be in one year?
And then to your question about the rocks, the Traction portion is what are you going to do over the next 90 days to lead up to that vision and be very disciplined about it.
So the VTO, Vision Traction Organizer, takes all of that, puts it on paper, and EOS forces you to update it quarterly.
So a strategic plan is often a consultant that comes in, a big book that's put on a shelf, everybody gets excited about it, and then on day one, well the world has changed- Mm-hmm.
and you think about where the world might be 365, 2 years, 5 years, well, that plan gets very stale.
EOS makes sure that you update it and makes sure that the traction to keep that momentum going remains alive.
So the VTO would be one of the core tools that is used from a strategic planning standpoint.
To your point, rocks are the little projects, and they're not that little, they're 90 days, uh, that you think are the priorities in the business.
Looking at my mistakes, don't do too many.
We think less is more now.
We thought more is more at the beginning.
So do 2, 3 as a business and, and, and really crush them, and that is the best way to get the momentum going.
So you have the rocks, and then you have this thing called the Level 10.
And we know as business leaders that it's not only strategic planning and these rocks that we talk about, 90-day projects, but it's also you gotta manage the business on a day-to-day basis.
So every Monday morning, the leadership team at Strategic meets and we have a 90-minute meeting called a Level 10.
Why Level 10?
Because we want it to be rated 10 out of 10.
out of 10.
We want people to want to be in a meeting that gets stuff done.
Mm.
We want them to think, "That was productive, not a waste of my time.
I don't have too many meetings."
Okay?
We want it to be productive so that the business momentum continues to move.
So we have a Level 10, 90 minutes, and it's not just the leadership team.
Each group within the business also has Level 10s, because each group has little issues and opportunities that crop up that need to be taken care of.
So within the Level 10, there is something called an IDS.
Okay?
Identify, discuss, solve issues and opportunities.
So during the week, instead of me going up to Jay and saying, "Hey, Jay, I got an idea," or, "I see an issue.
Let's talk about it right now," very distracting.
Yeah.
I got a job.
Put it on the IDS, and if it's a priority item on Monday, we will hit it.
If it's not a priority, we'll get rid of it or punt it to the week ahead.
So that is how we kind of clear out the noise and allow us to operate, I think, in an exceptional way throughout the week without being distracted by the noise, but making sure we're managing the business- Mm.
really effectively, week in and week out, within the, um, within the minutia that needs to be taken care of, but also, within that strategic plan.
So those are some of the- the core, uh, tenets.
Uh, there's others, like the accountability chart, not an organizational chart, not a hierarchy.
It is simply to say, "This is a job that we need to get done in the business.
This is what accountability looks like within that job," and then it's our job to find the right person, right seat, a cliche from Jim Collins, but get the right people in each one of those boxes so that they understand what is expected of them and they can execute for the business, anoth- another key.
So that was a long answer to just frame-
what EOS is.
How did it, um, uh, impact me and- and how did I model that behavior?
I tend to be a quick start.
That's a Kolbe term that analyzes how you operate in your natural environment.
And some people ask a lot of questions.
I tend to make quick decisions.
For me, this process ensured that I wouldn't make a bunch of quick decisions that left people feeling scattered.
It forced me to organize those thoughts, get them on paper, and be thoughtful about the execution, um, uh, around the answers that we discovered.
Mm.
And, um, hopefully, that- that behavior was noticed and- and beneficial to the business.
00:13:06,180.00000000011642 --> 00:13:06,420 Yeah.
And so I think there's a lot of interesting things in there.
And, um, one of the things I kind of wanted to- to pick out, out of your- out of what you just discussed, and what I heard was, in 2 different areas, is the first 90-day rocks were a lot, and you were trying to do everything, right?
Yes.
And I think that there was a story as well, along with the vision, was a lot- Oh, yeah, yes, yes.
when you first started too, right?
Yes.
And I think that's not a unique thing to us.
I've seen that at other companies, where the vision becomes almost this mantra, this like thi- where we wanna get everything.
Everything is our vision, right?
So when thinking about simplifying and keeping things simple, what- what kind of recommendations or- or guidance can you give?
What- what a great question.
That is why you're one of the leading podcasters in the country.
Um, I might have a biased, uh, a biased opinion.
Uh, I will mention, uh, before I answer your question, that, uh, Jay will include a link to the- Mm-hmm.
EOS website, uh, in this podcast, so if anybody would like more information about maybe how to run their business a little bit better, uh, you can look it up there.
Mm-hmm.
And certainly call me anytime.
I love this, I love this stuff.
So the fi- sorry, I'm laughing 'cause it really was ridiculous.
So we sat in a room, um, before we really knew what EOS was supposed to be, and we understood, well, we better institutionalize the great stuff that my dad and Judy brought to this business so that we never forget it.
And we spent an entire day coming up with our values, an entire day coming up with our purpose, and 2 funny things happened, or- or annoying things, however you think about it, 'cause it was, you know, pushed us off of 6 months or a year.
The first is, when we thought about our purpose, we had a whole paragraph that we tried, to your point, fit everything in.
"Boy, we better cover everything."
And then I called my dad up on the way back from Cooperstown.
00:15:06,410.0000000001164 --> 00:15:08,460 I said, "Hey, this is what we came up with."
And he said, "Yeah, that's great.
'We're just here to help people live a great life.'" And I said, "Geez, I could have used that this morning-" "
instead of trying to hash this out on a, on a whiteboard and- and capture everything."
To me, that is so powerful because it guides the people in this business and everything that they do.
When they pick up the phone, when they think about how to help people, it's not meant to be an exter- external slogan.
00:15:33,579.9999999998836 --> 00:15:50,660.0000000001164 I'm sure we use it sometimes, but it's meant to be the guiding light for every interaction for the people here, and it goes back to 1979, when most firms were just selling investment product, and my dad said, "No, they need financial plans," okay?
00:15:50,660.0000000001164 --> 00:15:56,432 "And they need a good partner to sit across the table from them and help them live a great life."
So, that is our purpose, and we try to find people that really are empathetic and care about that.And it's okay if you're not, but this is not the place for you if that's the case.
00:16:07,415.9999999998836 --> 00:16:11,776.0000000001164 So that was the purpose, and that was the first kind of funny but annoying thing-
00:16:11,776.0000000001164 --> 00:16:13,836 that I had to spend 8 hours, and then-
I should have just made a phone call.
And then the second is, uh, values.
And, and I think a lot of firms, from what I've seen, make a mistake by trying to please everybody and their values, and also have the table stakes stuff on the wall that maybe doesn't need to be said.
And my dad, my dad has guided me on this one as well, so shout out to him.
He said, "If you have to say integrity in your values, you probably don't have it."
00:16:43,74.00000000011642 --> 00:16:43,276.0000000001164 Okay?
00:16:43,276.0000000001164 --> 00:16:44,776.0000000001164 No offense to people who have it out there.
00:16:44,776.0000000001164 --> 00:16:47,996 I'm sure we had it in our first, uh, iteration.
But what we came back with was 5 inauthentic values that sounded like what any wealth management firm should be.
Mm-hmm.
And they sat there for about a year or 2.
I couldn't tell you what they are right now.
Integrity was one of them.
Excellence I think was another.
00:17:06,976.0000000001164 --> 00:17:13,215.99999999988358 Just meaningless stuff that, yeah, you better be excellent at your job and you better have integrity.
00:17:13,215.99999999988358 --> 00:17:24,985.9999999998836 Um, what EOS forced us to do was go back and say, "Who are the founders of this firm and what was the culture that they cared most about?"
00:17:24,985.9999999998836 --> 00:17:26,384 'Cause that is authentic.
I tend to think very simplistically.
I don't want, um, huge sentences or paragraphs.
Shorter the better, simpler the better.
And so we thought about Judy, we thought about my dad, we thought about the culture that we worked so hard to develop at that point over 30 years, 38 years maybe.
Um, and we knew this, that the culture of the firm was always serve.
00:17:56,956.0000000002328 --> 00:18:00,272 So to cut to the chase, the 3 values are serve, grow, and live.
Serve is the first one, which is to say when you think about helping people live a great life, you better be of service to them.
So that's the clients.
If your colleague, your team member across the way needs help, serve them, help them.
If the community needs your assistance, serve them.
And the firm lived that to the T on all 3 of those for years.
That's who we are.
Then if you think about Judy and my dad and this entrepreneurial spirit, if you have 0 assets and you wanna run a wealth management firm, you better figure out a way to grow.
And, um, it's easy to lose that because you can become complacent.
00:18:46,416.00000000023283 --> 00:18:50,056 And it's, it's not just growing assets under management.
We certainly want to bring in new assets, generally through client referrals, and we really want client portfolios to grow through market appreciation.
We, we
That's the key to our financial success.
But we also want the professionals here to grow in their skill sets, in what they're able to deliver for clients, in what they can look back on, um, when they retire and say, "Man, I really grew as a professional.
I became a lot better at my job."
And we want people to grow personally, uh, as well.
We want the services of the firm, if we have 0 assets and now 2.5 1000000000, well, we have a real opportunity to expand what we're delivering to clients.
We think about the plan, the financial plan that we have, uh, developed, uh, for our clients and adding services to that, or expanding the quality and the depth of those services.
Uh, the tax planning, um, um, is an example of that recently.
00:19:50,166.00000000023283 --> 00:19:50,816 Mm-hmm.
So, uh, growth was the second.
And the last one, serve, grow, live, ties obviously right back to the purpose, help people live a great life.
00:20:00,956.0000000002328 --> 00:20:06,176 We want that mindset, but we also want people here to live a great life.
And I've said this to you, Jay.
00:20:07,775.9999999997672 --> 00:20:28,016 I've said it to every new team member that we've brought on, and it is, "If you are making a commitment to this firm, it is at the same level as who you marry, where you live, what college you go to, those, do you have kids, those big decisions in life.
I want my career to be with Strategic Financial Services.
Mm-hmm.
What do we owe them in return for that commitment?
We want them to live a great life.
We want them to live.
And we want them to look back hopefully after 20, 30 years from now, uh, and say, "My life was better because I made that decision."
And I use this as the simplest example.
If any team member here is missing a recital or a game because of work, we're doing something wrong.
Mm.
We don't want any of that when they look back.
We want them to be there for their families.
We don't think it's a give-up, we don't think it's mutually exclusive between business success and living a great life.
In fact, we believe it feeds on each other.
So, um, the funny story there is we had 5, it meant nothing, they weren't authentic, we paused, and now, as everybody in the business knows, those are our 3 values.
So- Yeah, and- and I think from my perspective as somebody that's come on maybe, what, 8 years into you guys having EOS and kind of getting it, the engine running, um, honestly when I first came on and was- and was applying and stuff, uh, I saw that and, you know, Katie and- and everyone was explaining it to me.
I'm like, "Yeah, that's nice marketing."
Like, yeah, yeah, that seems nice.
And I just thought, you know, th- that's great marketing, but as I've come and- and been here for a while now, I've learned that that's really how the firm lives and- and I would recommend anyone who's thinking about implementing EOS or looking at your values or- or what you wanna be as a company, making sure you're living that so that as employees and team members come on, they feel that 100%.
Yeah, yeah.
'Cause otherwise it's disingenuous and- and you start to lose- Right on.
focus.
Oh yeah, right on.
Right, so- We can- we can add, Jay- Jay brought up a great question, I already flagged it with Holly who runs our HR and- and responsible for continuing to develop our training programs.
As we grow and now we have plus or minus about 40 people working here, we have big responsibilities to each other, and your question was how do you make sure EOS remains central, uh, to what we do, how we operate, how we lead, and I think we can do a better job of that so I appreciated that question and it is now added to an-
long-term issue which, when we have the capacity, will become a rock.
Yeah.
So thank you.
Yeah, of course.
Well, I think that's a good start for, uh, the podcast and I'd like to have you on and deep dive into EOS later, but I think we can leave it at that for today.
00:23:04,139.99999999976717 --> 00:23:04,800 Good enough?
Yeah.
All right, let's roll.
All right, and so like Alan said, we have, uh, if you check the links, uh, in- in the comments section, we will, and the description, we'll have all the links to EOS so you can check it out for yourself.
Excellent.
Thank you so much for coming on.
Nice job.
Thank you.
This podcast is for educational and informational purposes only.
00:23:24,639.9999999997672 --> 00:23:27,646 Please see the full disclosure in our show notes for more information.
Life by Design Podcast: Strategic’s EOS Story
Hello and welcome to the Life by Design podcast, brought to you by Strategic.
This podcast is all about helping you live your great life. Each episode features insights from our team and special guest interviews.
Episode Overview
In this episode, we sit down with Alan Leist, III, CEO of Strategic Financial Services, to explore how the Entrepreneurial Operating System (EOS) transformed the company’s approach to leadership, accountability, and long-term vision. From his first exposure to EOS through a podcast to company-wide implementation, Alan shares how EOS helped Strategic grow intentionally and sustainably.
Talking Points with Alan Leist, III
Alan takes us through Strategic’s journey with EOS, beginning with a search for better structure as the company grew in size and complexity. He discusses the “aha” moment when he realized the team was hitting a ceiling—not because of effort or talent, but because the business lacked a common operating language.
With EOS, Strategic adopted a clear framework that emphasized accountability, focus, and leadership development. Alan highlights how EOS empowered different team members to take ownership, strengthened trust across leadership, and gave the firm the tools to scale while preserving its mission-driven culture.
Key Points from Alan:
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What is EOS? EOS stands for Entrepreneurial Operating System—a simple, practical set of tools for running and growing a business.
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Why EOS? As Strategic expanded, it needed a scalable structure to maintain clarity, communication, and momentum.
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Implementation: Strategic rolled out EOS across all departments, adopting practices like L10 meetings, rocks (90-day goals), and scorecards.
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Leadership Impact: EOS gave leaders a common language and rhythm, increasing trust and collaboration.
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Results: The firm improved strategic alignment, decision-making, and leadership development—helping people lead more effectively at all levels.
Conclusion
Alan Leist’s story reveals how adopting EOS provided Strategic with the tools and structure to grow with purpose. It’s not about adding more complexity—it’s about creating clarity and empowering leaders across the organization. By staying true to its core mission while evolving how it operates, Strategic is building a strong foundation for continued impact and growth.
Disclaimer
This podcast is for educational and informational purposes only. Please see the full disclosure in our show notes for more information.