444 - The Leadership Shift That Makes IT Scale w/Demetrios Xarhoulakos

Mike Kelley & Demetrios Xarhoulakos

444 - The Leadership Shift That Makes IT Scale w/Demetrios Xarhoulakos

THE IT LEADERSHIP PODCAST
EPISODE 444

444 - The Leadership Shift That Makes IT Scale w/Demetrios Xarhoulakos

20
1 X
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00:00 | 00:00

Short Clips

Episode Highlights

Demetrios Xarhoulakos

GUEST BIO

Demetrios Xarhoulakos began his career producing CAD drawings and became the person colleagues called when technology stopped cooperating. That curiosity eventually led him into application support, global team management, cloud migration, and technology leadership for an international engineering business.

In this conversation with host Mike Kelley, Demetrios explains why solving every problem personally limits a leader's reach. He shares how he trained support teams to handle specialized tickets, connected technical groups that had been operating in silos, and aligned IT priorities with organic growth and acquisitions.

The discussion also covers follow-the-sun licensing, vendor scorecards, unused contract value, role fit on lean teams, and the difficult decisions that come with people leadership. Demetrios closes with a practical look at governed AI adoption, the support burden behind employee-built applications, and a future where IT spends less time reacting to tickets and more time enabling the business.

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Show Notes

Episode Show Notes

Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.

[03:14] Demetrios traces his path from architecture and engineering into CAD and informal technical support.

[06:31] A director warns that personally taking every familiar ticket will make Demetrios the permanent escalation point.

[08:42] He describes scaling from a global CAD support team into a 40-to-50-person applications organization.

[09:57] The team moves roughly 75 percent of its data from on-premises systems to cloud environments.

[11:55] Remote employees in some regions face five-megabit connections while working with large 3D engineering models.

[19:26] Technology priorities are tied to organic growth, acquisitions, and the company's strategic goals.

[20:32] Demetrios finds silos across IT, CAD/BIM, and development, then connects the teams around shared diagnosis.

[25:48] A license purchase reveals twelve hours of unused vendor training already available under prior agreements.

[31:45] An unlimited-budget question helps reveal what motivates team members and where they may fit best.

[34:38] Demetrios discusses the weight of letting someone go and learning that the person later found a better-fit role.

[36:23] The organization puts AI governance, enterprise accounts, authorized tools, and data protection around employee use.

[42:30] Demetrios predicts that traditional support will shift toward automation and business enablement.

KEY TAKEAWAYS

Teach the solution before becoming the permanent solution. Training service desk and workplace teams expanded support capacity while helping Demetrios move from technical expert to leader.
Domain knowledge strengthens business alignment. His background in CAD and engineering workflows helps him translate operational needs into technology priorities for the C-suite.
Cross-team communication improves diagnosis. A slow CAD application could point to hardware, software, workflow, or training, so help desk, CAD, and development teams need to investigate together.
444 - The Leadership Shift That Makes IT Scale w/Demetrios Xarhoulakos
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TRANSCRIPT

Mike Kelley: All right. Well, it's great to have you back for another episode of
You've Been Heard, the show dedicated to the IT executive currently steering
their organizations and the aspiring tech talent preparing for their own seat at
the leadership table. With us today is Demetrios Xarhoulakos, a seasoned I.T.
executive with a rich history of guiding complex technical transformations and
steering enterprise infrastructure. What really stands out in Demetrios
leadership philosophy is his sharp focus on operational excellence, vendor
alignment, and building resilient systems that actually scale with business
growth. He's an executive who knows how to navigate technical trenches while
keeping clear line of sight on the high level organizational strategy.
Demetrios, you've managed to transition from building technical frameworks to
driving corporate culture flawlessly. We'd like to hear how you did it. Can you
kick things off by introducing yourself and sharing your path to the executive
table?

Demetrios Xarhoulakos: Sure. yeah. Demetrios Xarhoulakos I currently work at
Disimone, consulting engineering, so I probably have a bit of a unique, story,
compared to some of your other, panelists. So, I started in the architecture and
engineering field. and Disimone is within the architecture and engineering field
as well. and so, early nineties to date myself too much. I was, like a CAD
designer. So computer aided design is a means of delivering, construction
documents. And so I grew an expertise in that field for years. And I did that.
and I always was the person in the office who was the most technical, the go to
person for technical questions about the software we were using. I like to
figure out how things worked. I ended up, kind of I would also answer it
questions too, right? It kind of evolved from there. Right. so, I did that for
years and I was always kind of that position. And then, early two thousand,
where a major architecture firm in New York City, I reached out to me and they
were looking for somebody. Basically, it was an IT help desk position, but
focused on the CAD side of things. Right. so instead of me doing drawings and
construction drawings all the time, I would be the help desk for the people
doing the CAD drawings every day. And the thought of that was my first instinct
was, oh I didn't know this was a thing. Sign me up. I would love to do that.
Right. So because it was something I was doing already. and now it was something
that I could just do full time. The challenge I had at that time was, a
bill-able work versus being doing, helping people and things. That was a
challenge. so that was kind of the start of my transition. and I did that for a
few years. and then I started, about ten years ago now, I started this company
called Mott MacDonald and they had brought me in, as an IT manager, with a focus
on that CAD kind of world. and that was my kind of first foray into management.
Right. And more strategy and more strategic thinking and the more diverse I.t
world. Right. I had exposure to that, at the firm in New York as well too,
because I would work hand in hand with help desk, people, right. So a common,
thing that we would face is, somebody having trouble with their computer and, it
could be the software, it could be the hardware, it could be a number of
different things. And we would work closely together with the help desk people
to kind of determine what the kind of root cause of some of those problems were.
so when I transitioned to Mount MacDonald, those are kind of brought me in for
that expertise. and it was four hundred person IT company. and that was the
first time I'd been a part of a big company and a big IT team. and it was a bit
overwhelming at first. knowing who to talk to, where to go, where to turn, and
kind of an eye opening moment for me. about a month into my position there, I
see these tickets coming in, regarding CAD and things that I have solved over
the years, hundreds of times I could do it in my sleep. And I remember going to
my IT director at the time and saying. should pick up these tickets, keep in
mind there's a four hundred twenty four hour service desk, local help desk,
workplace team. but I'm seeing them come in. I'm not seeing them being picked up
and I'm like, should I just pick these tickets up and do them? And, he said
something to me that really kind of hit home. and it was a bit of a shift in
mindset for me was, he said, you can, but be careful what you wish for. because
if you do, those people will come to you forever and ever. but instead, is train
the people that are underneath you train the local workplace team on how to pick
up these tickets, train the service desk, the L1, L2 teams on how they can pick
up some of the easy quick wins, and then train the local teams and work with
them and be a support for them and guide them and train them. And that really
kind of like was an eye opening moment for me. going into more management.

Mike Kelley: Yeah. And actually, I think that's, out of all of the interviews
I've done, you're the first person that has verbalized that well, in that sense
of, it's so much we have that analogy so much like with the help desk, when the
help desk teaches somebody how to fix something and instead of just saying,
here, move out of my way. yeah, then that user learns how to do this, but now
you're talking at it at a different kind of level. And I've never heard anybody
else verbalize it like that. And so I think that that's a key point for any of
our listeners right now who are trying to make changes in the ranks and move up
the ranks, help teach those to do that for you instead of taking it all on
yourself. Because in doing that, you teach them, they become more valuable and
you begin to lead, which is where, we left off. You starting in the management?
Keep going.

Demetrios Xarhoulakos: So that really kind of was eye opening for me that when
he told me that. And that's the approach I took going forward in that position.
when I needed to be technical, I needed to step in, I did, I still enjoy getting
my hands dirty. So, there, I managed a global applications team. so at first I
was managing the kind of the CAD support team. and that was about a ten person
team strategically positioned globally with a number of challenges. That comes
with one being time zones. So, I was working from home long before Covid even
happened. just because of that nature of it. I would be on phone calls with my
team in Singapore and India and, eleven o'clock, twelve o'clock at night. and
so, that evolved into more broader application support teams. So, the Microsoft
team, was underperforming. at the time, they moved that team was again, a team
of twenty people, level three, level four team. that was managing the Microsoft,
the full Microsoft tenant. and then, at that point, I had grown to about forty,
fifty person team, covering all applications, throughout the company. So
everything from the CAD design software applications to the Microsoft side and
everything in between. So this was strictly applications we work closely with,
obviously with infrastructure. We work closely with them. we were, when I first
started there, we were all of our data was on prem in data centers. we were in
data centers in the US and the UK and in Singapore, Australia. and we shifted to
cloud. so we moved about while I was there, about seventy five percent of our
data from on prem to cloud. so our focus was on all of our on prem license
servers for all of our applications. and moving that, to cloud based licensing,
license management, data management, cloud, based licensing. So that was Azure
cloud was where we moved to. So we worked very closely, obviously with the
infrastructure team. in that process.

Mike Kelley: If you don't mind me asking, what time period are we in now? Are we
in the mid twenty ten.

Demetrios Xarhoulakos: Late mid to late twenty tens. Yep. Okay. Just pre-COVID.
Yeah. When we did the Azure migration.

Mike Kelley: Okay.

Demetrios Xarhoulakos: Covid happened, of course. and, a challenge for
everybody. I think the big challenge was, ensuring, people were able to work
from home, connect from home, as much as possible. My big focus at the time was
license management and ensuring that they're able to connect through, VPN or
whichever mechanism we were using at the time. I don't remember, but being able
to connect, and pull the license and software and, keep working. That was a big
challenge. working, we're obviously working really closely with vendors through
that process.

Mike Kelley: And then can I deviate for a second again in the questions because,
I'm not sure how many people I've talked to that were running something like
that during Covid. Were there any challenges to providing that service
internationally during that time? Because I know that, I only had to deal with
domestic and, one of the things that surprised me was how many of the people
that put up their hand and said, ah, I don't even have internet service at home,
let alone my own computer. which was surprising, but internationally, what did
you run into? What was different about this in an international scope?

Demetrios Xarhoulakos: So certainly the internet was an issue. there are a lot
of people internationally lived in very remote places. so they commuted to an
office that had good infrastructure and high speed internet. but back at home,
it was a challenge. and, they were dealing with five megabit download speeds or
less. Right. and in the architecture and engineering field, we're dealing with
massive large 3D models. that could be anywhere at the time. average file size
was five to ten terabytes going up to gigabytes or five to ten gigabytes going
up to twenty, thirty gigabytes easily. and then constantly. And so they're all
cloud based, right? So constantly pulling, drawing down that data over a five
megabit internet connection was definitely a challenge. so that was a challenge.
we had to make some arrangements for those special cases for people to be in
office. And, we'd work locally with the team, make, with safety requirements, we
work closely with HR and everybody to kind of make accommodations for people
where they had to be in office. We had people also speaking of Covid, who only
wanted to be in office. they made a big stink. They said they can't work from
home. it wasn't even a case of internet or anything like that. They just wanted
to be in office. and so I had two people on my team specifically that really
kind of wanted to do that. And again, we, kind of worked locally to, with the
team to be able to make those accommodations. But yeah, the internet was one big
thing for sure. working with our vendors as well. So vendor management is a big
thing that I, do, and I still do to this day. in this field, we work with a lot
of different software and vendors and so coordinating with them, we had just
transitioned a year or two prior to that, our licensing to the cloud. And so
that presented a, some issues with the time zones, and people logging in at
different time zones and things like that. but yeah, for sure the internet, what
was an issue?

Mike Kelley: And so with the international and the time zone differences that
also changed the approach to the data centers too, I'm sure, because like, one
of the advantages of cloud and, is the ability to spin up resources and spin
down resources. Follow the sun. And since you've got people that are following
the sun the whole time. Yeah. Oh, man. You're your resources. Did you. Yeah.

Demetrios Xarhoulakos: We're constantly. Yeah, So, in that transition to Azure,
we were working with a vendor, building, VMs on Azure, to help accommodate that.
work spot is one that comes to mind that we were using where you could literally
spin up and spin down, machines. And so that would help with the follow the sun
mentality, the licensing. and again, we had, obviously we had our vendors and
end user license agreements to ensure that this was compliant. but, we built a
system within Azure and the license server. So that way if, somebody, kind of
working in shifts, right? So somebody was working for eight hours, they'd hold a
license and then they'd sign off and the next person would, coming online in
Singapore or India, wherever it was, would be able to pull license. and then
when they overlapped, it sometimes became an issue. So we had to put some
measures in place, to allow for that buffer. but yeah, the license management
across times is always kind of, it was more of a challenge when it was on prem.
where in that scenario where, there was a bit of crossover where there was times
where we were double dipping, with the licensing, which wasn't an issue from end
user license compliance, but it was more of a cost issue where our vendor would
come to say, hey, you need one hundred and fifty, right? and then we're like,
why are they saying that we need this many licenses? And then we look and we see
that there's a double dip there because of the time zone crossover.

Mike Kelley: Yeah, and interesting. So and for me, I'm recognizing right away
that you're using device calls instead of, people calls or user calls. Because
then with the user Cal, it's one per person, doesn't matter what time zone or
when they're using it, but the device one you can share between two people. So
yeah, that one depending, I've never thought about it following the sun like
that or moving from data center to data center.

Demetrios Xarhoulakos: and depending on the license agreement too, right? So
yeah, if it was named user licensing, right? that presented much more of a
challenge to, be able to do that. But if it with a shared network license, that
was easier to do.

Mike Kelley: Yeah. And well, that one right there is, I tip worth its weight in
gold if you don't understand what we're talking about and you're dealing with
things like that, you need to understand what we just talked about. Yeah, yeah.
For sure. All right. You, brought up that point of, hey, teach the staff how or
teach the other guys how to support this. what are some of the other executive
leadership things that you've learned and how you've learned to lead the team
versus be the hero?

Demetrios Xarhoulakos: Yeah. So, just going back to like kind of my story, I
guess, I think that will lead to it. So I, post in late twenty twenty three,
twenty twenty four is company reached out to me and, they had a gap in
leadership around technology and the unique thing about architecture and
engineering companies and it comes to technology leadership, a lot of times you
probably, I mean, it's probably not just in architecture and engineering, but a
lot of times the most technical person, the most productive, most technical
person, when there's a management opportunity, like, oh, let's make this person
the manager because they're really technical and they're really productive in
what they do, but doesn't always translate to the best manager. and I had an
experience like that very early in my career where I became like a CAD manager.
Right. and it didn't quite like work out for me. Well, in that sense, because I
was still just very, very technical. and at that halfway through MacDonald and I
kind of transitioned more to the management, the strategy side of it rather than
the technical side of it. and so the gap at De Simone was. Yes, leadership. Yes.
Understanding the technology and the uniqueness of the technology in the CAD
world. and how that correlates with the needs of the company. and so a lot of
times, the architecture firm I worked with in early two thousand, there. IT
director was a licensed architect, right? so it's about knowing the business,
understanding the business, understanding the needs of the business. and so they
had reached out to me, late twenty twenty three, early twenty twenty four. and I
ended up starting here and I reminded myself of the architect that was the IT
director at that architecture firm where it's like, yeah, while I don't have the
traditional I.T. background, I lean on my team for a lot of that. I've got a guy
who's, who's an expert in infrastructure, a security expert. right. I've got the
help desk guys, right? So we've got our kind of our team, our well-rounded team.
and my focus is managing them, putting them in the right place to succeed. And
then also aligning with the C-suite, aligning with what they need. what the
direction of the business is going, and how do we kind of help them? How do we
help them get there? one of the things that the big focus this company I'm with
now is, growth. you touched on that in the intro. and we're growing in two ways.
One through organic growth, big projects, we do, high rise buildings, structural
engineering for high rise buildings, fifty, sixty story buildings, residential,
commercial. and so there's been a lot of growth in that field. and then mergers
and acquisitions. so we do a lot of M&A work. So we're partnering with, and
acquiring smaller engineering companies. and the idea is to build a bit of a
more diverse portfolio, within the business. and then so for us, it's, how do we
tackle that? Right? So anytime there's M&A, there's an integration, we're doing
one right now, to integrate them. And so that presents a challenge. so it's
aligning what we do with the business with what their strategic goals are,
whether it's M&A, whether it's organic growth, keeping up with the technology in
the specific space. and then building out that team, partnering with, other
technical. So there's people here that do what I used to do and that kind of CAD
support role. And so I love talking to them because I could talk their language.
Right. and one guy kind of was a bit inspired when he first met me. He's like,
you used to do this, right? And now you're the director of it. and so in this
field, it's very common transition to kind of transition from that the project
delivery work into more of a technical kind of role if that's the direction you
want to head. so that those are some of the things I'm really focused on around
the kind of the management and the leadership.

Mike Kelley: Okay. did you run into any of those other moments that just really
stuck with you like that, one that you shared at the beginning of, teach them
versus, do you want to become the only person that supports it?

Demetrios Xarhoulakos: So for sure, for sure. So, when I first started here and
it's probably still a thing. people, there's a lot of silos, right? So, we have
the traditional IT team. We have the cad BIM team. we also have a bit of an R&D
team, which is some software developers, right? And everybody's kind of working
in silos a bit. and, when I was early on here, I overheard one of the guys in
the team saying, oh, we've got this ticket with this CAD software. somebody's
saying it's really slow. we need to go and repair the computer. We need to go
reinstall the application, we need to do these things. And so in a kind of a
light bulb came off to me. I was like, hey, has anybody checked with the CAD
team to see what they're doing? Like, Is it the hardware or is it the computer
or is it the software? is it how they're using their software? They need more
training. So, I connecting those pieces, those dots, those silos, tearing down
the silos and connecting the, yeah.

Mike Kelley: Talking to each other.

Demetrios Xarhoulakos: Getting them, talking to each other, getting the help
desk guys, talking to the CAD guys, to the software developer guys, right? Like,
and it's tearing down those silos. and we're getting there for sure. I meet
regularly with the CAD team. just first thing this morning he was over by our,
the IT area talking about an issue that came up. And so that's what we want,
right? More in communication. So I think for me early on here that was probably
that that big one is tearing down the silos, and get people talking to each
other.

Mike Kelley: So that's a unique one usually because I'm used to hearing about
those silos within the business and then trying to break down those silos
amongst the because then you got ten different chiefs and they're the only ones
that are important or their job and their challenges are the only things that
are important to them. But then you've got to balance that for the whole
business. but to walk into an organization where the silos are in the, IT or the
overall group.

Demetrios Xarhoulakos: Yeah.

Mike Kelley: So you guys as the engineering firm, you're just building all the
plans and doing that piece. How much of the actual build are you guys involved
in? Or do you guys just hand it off and then a construction company comes and
takes it.

Demetrios Xarhoulakos: Yeah. So, that's a good point. Just on the technology
side to touch on your question. so we, usually we partner with, our clients a
lot of times our architects, right? So architects get hired to design a tall
building. They begin the design. They engage with different engineer, like a
mechanical engineer, a structural engineer, a plumbing engineer. Right. so
structural engineer will work with the architect to design that building. some
engineering companies will go through the entire process of designing and then
building as well, where we design and during a build phase, we're more of a
consultant, right? So as it's being built, if something's not right, the
drawings, we're coordinating the contractors on that build according to the
architect, according to the contract. so we're in it until the building is
built. for sure. It's just a matter of, we're more heavy in during the design
side of it. And so.

Mike Kelley: Still international or you just domestic now.

Demetrios Xarhoulakos: global, we have offices. Okay. Yeah, we have offices and
twelve countries, but projects, globally.

Mike Kelley: When you said Desmond, I wasn't sure whether it had shrunk down or
was still global.

Demetrios Xarhoulakos: So yeah, we're, global and growing. but yeah, so with
construction, we deal with a lot of technology on that side, right? So, the
drones and cameras and all different things. And so managing that is.

Mike Kelley: Software's, the 3D renderings, the. Yeah. I've had a chance to talk
to a few of the people in your industry, usually at a smaller scale, but having
a little bit wider breadth of responsibilities. And so yeah, there's a whole
different world to that side of this. So, tell me a little more about the vendor
management and those pieces like my team, we've got some challenges when dealing
with third parties and especially when we bring in a third party to augment the
team in any given way, there's a lot of times where the team is frustrated
because they feel like they have to go clean up after the third party. are you
guys doing anything when you're talking vendor management, are you dealing with
that or are you just dealing with optimizing things like the Microsoft licensing
at a global scale and making sure to really optimize your spend?

Demetrios Xarhoulakos: It's a little bit of both for sure. Yeah. I mean,
obviously spend management is a key thing. that we do, it's one of the reasons
they brought me in for that, for sure. I report to the CFO. so on vendor
management side, my approach really is, building relationships with them. and
really partnering with them to ensure, we're getting the most value out of our
investment, right? And whether that's through the license optimization, whether
that's through getting the right training, for the people using the software,
and really working with them to get the most out of it. I'll give you a good
example. we're working with a software vendor recently and we had to purchase
some additional licensing. And they had mentioned during that procurement that,
they are offering, some training, two hours of training, because we purchased
those licenses. And so I reached out to the team had requested it. and they
mentioned, they were interested, let's send them what was available. And then
the vendor had said, yeah, and actually you guys had it, you have about twelve
hours of unused training that you hadn't done before from your previous
procurement software. And so that's the kind of thing there, right? It's like
understanding what we have, what we're getting with our contracts, right?
Understanding what is the full value of we're getting if we're just buying a
piece of software and handing it off to people and say, hey, go do this thing,
go build this building with the software, and we're really getting the right
value out of it. And maybe if there's an expert, there's somebody we hired who's
an expert in software, maybe, but a lot of times not. Right. so building those
relationships, understanding the value of it, of course. Yeah. The license
optimization part of it is huge. And the vendors don't like hearing that stuff.
for sure. they just want to sell us more. And so, it's finding that balance and
working with them to, do that. Yeah. So, with a number of, A hundred plus
vendors that I work with currently in my current position. There's more. When I
was at Monmouth, Donald, and, I do a quarterly review of each. So the big ones.
so if a million dollars plus contracts, we'll do a quarterly review. That review
will have, a grade. and that grading is based on license optimization. It's
based on training. It's based on engagement. it's based on our why. and that's
my approach.

Mike Kelley: Wow. Okay. No, that's a wonderful, bit of experience for us to
learn from too, because I'm so used to the flip of that, where the vendor comes
in with their quarterly business review and they tell us how we're doing as a
customer versus us talking to them and telling them how they're doing as a
vendor. Yeah. yeah. I've always taken a stance or not always. I've learned to
take a stance of just being forthright and very honest and sometimes brutally
honest. But, it's all in the delivery. on how you I.

Demetrios Xarhoulakos: Had a software vendor, we were doing a big three year,
twenty million dollar contract. we were doing a three year renewal and in our
first meeting, they came to me and said, here's your projected usage over the
next three years. I said, what, you're giving me my projected usage? No. Right.
So I'll tell you what our projected usage is. And all they did was they did a
straight line horizontal usage report, right? I'm like, you're not factoring any
of our actual business needs. and so yeah, of course they try that. Of course
they do that here's your quarterly. with our major vendors, I do that approach.
I do the flip side of it and, it's more, it's not something I show them, it's
more like I show my C-suite that they see that, what, how they're performing.

Mike Kelley: Yeah. Because I think that.

Demetrios Xarhoulakos: They can pull it out. Of course.

Mike Kelley: Yeah, yeah. They can plan it out. and you're not beholden to them
because I switched organizations, a couple years ago. and one of the vendors
that we were working with or that they had been working with, already had
contracts with came in and we're talking about that and, oh, here's your
projected user growth over the next three years. And we're like, guys, we're in
the middle of a recession right now. Things are not going well. transportation
is like down.

Demetrios Xarhoulakos: Yeah.

Mike Kelley: We're not seeing that. We're not hiring new employees. As a matter
of fact, we're about to cut a bunch of employees.

Demetrios Xarhoulakos: Yeah, it's a challenge finding that balance of dealing
with the sales stuff. Right. but understanding what you really need. Well,

Mike Kelley: it's also a challenge on that of finding the balance between them
trying to find the intersection of value and us trying to find the intersection
of value because there's a lot of times where they come in. So what are your
plans for the year? and they just try to find. Yeah, tell me because I'll find
some way where I can intersect with it versus.

Demetrios Xarhoulakos: Better tell me they want to see my roadmap. Yeah.

Mike Kelley: I'm just like, no, no, I want to know what value you can bring or
where do you guys really do well? And then I'll see whether that fits into my
plans versus where you can see, oh, I can get you licenses for that. I can get
licenses for this. All right. What about the building of the teams? What other
things do you do to help build. Yeah, the, high trust teams. And you mentioned
making sure that you've got the team and finding the opportunities for them. So
when you found somebody or you've identified somebody who's not firing on all
cylinders or is not living to the potential that you believe that they have, how
do you help find what's the right place for them, even if that place is at
another opportunity?

Demetrios Xarhoulakos: Yeah. Right, team management is certainly a passion of
mine as well. again, evolving from the strictly technical role to the management
role, right? This is a newer, kind of newer ten year last ten, twelve years,
right? Where it's really become more of a focus in my strategy and my management
skills in proving that and building teams. so what, like give you an example of
what I did when I first started this is, one of the hardest things to do when
you're coming into a position like this is evaluate the current team, right?
Evaluate there's a reason why you were brought in. and one of the things you
need to do is do that full evaluation down to each individual, on how they're
performing, individually and how the team is performing overall. and there was
one specific person that had already been kind of in a pit, but prior to my
joining, and they had mentioned it to me early on, even during the interview
process. and I said, I'm happy to kind of, take that challenge on. I embrace,
working with people who have struggled in the past, maybe they weren't inspired,
maybe they didn't have the right tools to support whatever that is. and so there
was two people that kind of fit in that boat when I first started here. and so
the approach I took, with them was meeting one to one, of course, but really
kind of trying to understand what makes them tick, what really makes them, get
up in a day and want to come to work. I like posing the question to them. If you
had an unlimited budget, what would you do to improve our digital landscape
here? What would you do with an unlimited budget? Right? A lot of times, some of
the answers I get, they're actually, something that is reasonable, and so if I
get kind of deer in the headlights, blank stares, I'm like, okay, right? Like,
tell me what really inspires you. And so anyway, I determined kind of through
those conversations, what would be the best fit for what they wanted, but also
what we needed to do and what we needed to accomplish. with one person, it
worked out. he kind of, really found his niche. and he's that kind of fits in
that very, very technical kind of role. And he likes, tapping at the keyboard
all day long. And that's what he likes to do and kind of head down. and that's
okay, right? You need those kind of people. and so, the other person really
struggled. I don't think he'd been here a long time. he really struggled with
kind of finding that right place and a couple conversations. I was like, is this
really what you want? Is this really what you enjoy doing? And unfortunately, he
did not work out. the other person, but, we tried. Right. And so that's kind of
my, approach, like, we're as a team, we have a mission. that aligns with the
business and the strategy of the business. and then I work with everybody
individually for them to meet their goals and then align that with the team
strategy and the business strategy as well. we make hires when we need to. We
let people go when we need to. which is the absolute, of course, last resort. we
do training. everybody, in the team is required to do some form of training,
every couple of months or so. we regularly have training sessions on, a number
of topics, kind of the team that I've got at the moment, each have a good skill
set individually. the one guy says infrastructure, another guy security. Right.
But we're a bit of a lean team and, you have to be somewhat well-rounded. You
have to be able to pick up something, when it's thrown at you and no one else is
around to help. And, you're kind of thrown at you. And so we do that by sharing,
kind of sharing knowledge and doing training sessions, and things like that.

Mike Kelley: So talk to me about some of the lessons you learned and the
struggles, because you mentioned you've had to let people go in the past. So, I
know that the first couple of people I had to let go, I really struggled with
those. But then for me, the experience of letting them find new opportunities
and bringing somebody else in, once I was able to look at it in hindsight, once,
that was all said and done, the person that came in afterwards was such a gift
that I started to kick myself going, why didn't I do this sooner? Why didn't I
help them? Because I've also had some of those people come back to me too. Those
ones that I helped guide towards another opportunity going, hey man, I hated
doing this, but but I ended up here and life is great. So what experiences did
you have along those lines?

Demetrios Xarhoulakos: when that happens, I cannot sleep at night. it's still
hard for me. the most recent experience with the, the example I gave, so again,
it definitely was not the right, like because we're a lean team and you could be
working on a project, right? delivering some new piece, of infrastructure or
something, but a security project, some security initiative we're doing for the
next thing you're doing ten tickets, right? Like it's like we're all kind of
chipping in. I did two tickets the other day. Right? So, he struggled with that.
he had a very kind of niche, skill set that he did. and there were times where
we struggled with that as well. and so he really struggled with that kind of,
you would say, I don't want to do this. I don't want to. And so anyway, after
that happened, a couple months later, somebody here in the office who I know was
very close with him. I asked him, if they had spoken to them and if they were
doing okay and things like that. and they mentioned that yes, he found a new
position making more money. and, his first comment was he's happy. he doesn't
have to do any tickets. and I think for him, it was probably what he needed.
Right. And that the friend who was still here said the same thing. It's like
it's exactly what they needed.

Mike Kelley: Yeah, exactly. It's one of those challenges. And then realizing
sometimes that it's okay because yeah, it sounds like you take it very personal.
Yeah. And you can't help somebody to succeed. But sometimes that's just the way
it is, unfortunately. Yeah, yeah. so. All right, we can't get any or through any
conversation without bringing it up. How's it being layered into your
organization? How are what are you guys dealing with that topic that shall not
be mentioned. And I know you know what I'm talking about because I see it on
your face.

Demetrios Xarhoulakos: I know what you're talking about. so one of the things
that we've tackled recently, is the governance around it. So it's being done,
it's being used. People are jumping in, they're doing it. My CEO is in my ear.
What are we doing about this? what are we building? What are we going to do? I
want a full LLM because he heard it on some podcast. So yeah. and my CFO has
told me, no, we can't afford it. Right? and I was always the person I was
pushing the buttons. Right? so I want to enable that for people, right? But my
thing is I want to do it in a managed way, right? Not just wild west. Right. for
sure Wild West is happening, right? People using all the different services out
there. without any kind of oversight over it. so we've made some investment in
some of the more common AI tools out there. we've got enterprise accounts with
them. So we're telling people, look, we've made the investment, we've got the
tools. and this is kind of from the C suite coming down what they're asking.
It's like they ask is, I want to put this in the hands of people and I want to
see what they can build. and I think what we're seeing is people that you least
expect it are some of the most common users. so we invested in some, seeds,
we've made it available people, we've got a policy document that is required to
sign by everybody. now, especially if you're going to be using any of it, that
policy document essentially says, if you're going to use something, these are
the tools that we have that we own under our tenant. and this is what you're
authorized to use if you're on a decent piece of equipment. Yeah. if you're at
home, do whatever you want. but if you're on a decent piece of equipment, you're
on a decent laptop, iPad, phone, whatever, you need to be signed in with your,
SSL, MFA and all these things. So within our tenant, and kind of in a protected
way, if that's as much as you guys.

Mike Kelley: Yeah, I was, I'm wondering. So did you already have the DLP? Well,
you guys have a lot of intellectual property in those designs and everything
else. So you probably already had your DLP solid prior to this.

Demetrios Xarhoulakos: We did, but AI throws a monkey wrench into it. Right? So
the moment.

Mike Kelley: It does.

Demetrios Xarhoulakos: So, the moment somebody uploads a set of drawings into
one of those platforms, that protection is gone, and so that's the approach. So
if somebody is planning something nefarious in that building a set of those
construction drawings is highly valuable. Right. so there's a number of security
risks there. of course, the data protection that we want to have for our data,
people's social security numbers and banking information, all these things. and
so that was the approach we're taking that I would say compared to probably some
of the other people you're talking to, we're, I think we're in our infancy with
this, right? We're just trying to kind of get our head around it, putting it
into tools of people. I'll give you one example of something. Somebody built, we
had this massive spreadsheet. So structural engineering, right? So structural
engineering does a lot of heavy math, algebra, calculus, like really, really
heavy math. And we've got these spreadsheets that do a lot of that heavy lifting
for you, right? And this one particular one, it's a load, basically a load
calculation spreadsheet. it's been around for about twenty five years or
something like that. And it's constantly breaking. And when it breaks, everybody
looks to see who's going to fix it. Everybody throws their hands in the air.
Right. and so somebody built a app, essentially an app to replace that
spreadsheet, right? So it's like you you put in the inputs, the parameters of
it. you can even link it to your floor plan, right? Ties back to your floor plan
and the loads you put in the height of the, floors and the columns, the size of
the columns and things, and it outputs out your calculations. And that's really
critical for our project delivery, obviously, from a project delivery
standpoint, kind of doing a QA on the drawings. but also from a liability
standpoint, once the project is completed, we can show that we did the
calculations are done and things like that. so that's the kind of example of
what we're doing now is how do we take workflows and processes that have been
embedded in our culture for years and years and years that have never really
been rethought of how the approach on how to do it. And could some of these
tools help us maybe kind of get there? and so that's kind of we're putting in
the hands of people to see what they do. And the person who did that, by the
way, it was not the first, kind of not the top of the list of people, not the
most technical person necessarily, you know what I mean? But it's just like
with, plain language you and vibe coding. You could do some interesting things.

Mike Kelley: Some amazing stuff. Yeah. and it's great when you get a chance like
you mentioned earlier, it's the way we've always done it. Or the other one that
I hear a lot is if it's not broke, don't fix it. Yes. and for me, if it's the
way we've always done it, should we still be doing it that way? And if it's not
broke, let's break it and make it better. And these LMS give us a whole new
world or a whole new perspective on some of these things, that it's a perfect
chance to just try some of this, hopefully in isolation versus by coding in
production or on the production system. Exactly.

Demetrios Xarhoulakos: Exactly. Yeah.

Mike Kelley: And it's definitely something you got to watch out for.

Demetrios Xarhoulakos: So from an IT standpoint, right. That's the challenge for
us now. It's like, okay, they're building these things. Where does it exist?
who's managing it? Who's supporting it? What's the infrastructure behind it?
Right. there's vibe coding. You're just just going to build it on your desktop,
right? so.

Mike Kelley: When it's broken.

Demetrios Xarhoulakos: Yes, yes. Yeah. So that's a challenge for software
development for years and years, especially internal software development. hey,
if you build it, you better be prepared to support it or.

Mike Kelley: I'm going to catch you kind of flat footed with a question we like
to ask our guests, unless you've been listening to us and that is, what's
something that you predict that we'll be talking about in eighteen months that
we're not talking about today? or make a prediction about eighteen months from
now? A year and a half.

Demetrios Xarhoulakos: Yeah. That's an interesting one. So I think going back to
kind of just our recent conversation. At support in the kind of traditional way
that we think about it, I think is going away. I think of it more becoming
instead of a IT support team. Maybe it's an automation support team, right? one
of the things we're doing is kind of automating a lot of our everyday tickets,
right? Password resets and MFA, like a lot of that's triage and a lot of our
ITIL processes, we're doing as much as we can to automate. So the idea is to
free up the teams for a lot of the tasks that they spend so much time on day to
day, to better enable the business and what they're building and what they're
automating. So to the point you were saying before about, okay, yeah. Where does
it exist? Who supports it? Right. So if I could free up the team from doing one
hundred tickets and taking a day, let's say one hundred tickets a day, and I
could chop that in half and automate half of those then that the fear with any
new technology is, oh, people are going to lose their jobs. I don't like that go
by that at all. I, my mindset is I want to automate these tickets and then free
you up to go do bigger and better things. So if we got people building things in
the business, but they don't understand technically how it all is going to work
in the infrastructure side of it, that's what I need you to do because you
understand that, right? So that's where I feel like it's in eighteen months, I
will be doing more of that, right? Like it is shifting more away from kind of
traditional support, like the reactive support more to, Enablement, with the
business, working with them to do that and the examples of, working with the
team, right. And like working hand in hand with them understanding their need,
right. And then working with them to kind of facilitate, a lot of the things
they're seeing, what can we do to do that? So for me, that's the first thing
that comes to mind.

Mike Kelley: Okay. Yeah. Those will be some interesting discussions. and I hope
to see that how on target you are how? Well, it's been a great conversation.
Demetrios. It's gone by quickly. I don't know if hopefully as quickly for you as
it went by for me. hey so is at the end of the day, when you've secured the
environment and empowered people, is there any other final message that you want
our listeners that youvebeenheard.com or that You've Been Heard community to
hear or to share.

Demetrios Xarhoulakos: Yeah. I think wherever you are now, in the path that
you're on, it. You never know where you're going to be, I mean, again, thirty
years ago when I was doing CAD drawings on a DOS computer, by the way, I think
it would be the director of it, a big engineering firm, and so I think, stick
with your passions, and follow what you really are passionate about and that
will kind of lead you to happiness, I think. And that's kind of what for me,
I've always done that. I've been that person in the office that's the most
technical person, the go to person. I loved it, I enjoyed being that person. and
so that kind of led me to this path.

Mike Kelley: Yeah. Well, thank you again. Thank you very much for your time and
your expertise and sharing all of that with us.

Demetrios Xarhoulakos: yeah. Appreciate it. Thanks.

Mike Kelley: All right. Well, it's great to have you back for another episode of
You've Been Heard, the show dedicated to the IT executive currently steering
their organizations and the aspiring tech talent preparing for their own seat at
the leadership table. With us today is Demetrios Xarhoulakos, a seasoned I.T.
executive with a rich history of guiding complex technical transformations and
steering enterprise infrastructure. What really stands out in Demetrios
leadership philosophy is his sharp focus on operational excellence, vendor
alignment, and building resilient systems that actually scale with business
growth. He's an executive who knows how to navigate technical trenches while
keeping clear line of sight on the high level organizational strategy.
Demetrios, you've managed to transition from building technical frameworks to
driving corporate culture flawlessly. We'd like to hear how you did it. Can you
kick things off by introducing yourself and sharing your path to the executive
table?

Demetrios Xarhoulakos: Sure. yeah. Demetrios Xarhoulakos I currently work at
Disimone, consulting engineering, so I probably have a bit of a unique, story,
compared to some of your other, panelists. So, I started in the architecture and
engineering field. and Disimone is within the architecture and engineering field
as well. and so, early nineties to date myself too much. I was, like a CAD
designer. So computer aided design is a means of delivering, construction
documents. And so I grew an expertise in that field for years. And I did that.
and I always was the person in the office who was the most technical, the go to
person for technical questions about the software we were using. I like to
figure out how things worked. I ended up, kind of I would also answer it
questions too, right? It kind of evolved from there. Right. so, I did that for
years and I was always kind of that position. And then, early two thousand,
where a major architecture firm in New York City, I reached out to me and they
were looking for somebody. Basically, it was an IT help desk position, but
focused on the CAD side of things. Right. so instead of me doing drawings and
construction drawings all the time, I would be the help desk for the people
doing the CAD drawings every day. And the thought of that was my first instinct
was, oh I didn't know this was a thing. Sign me up. I would love to do that.
Right. So because it was something I was doing already. and now it was something
that I could just do full time. The challenge I had at that time was, a
bill-able work versus being doing, helping people and things. That was a
challenge. so that was kind of the start of my transition. and I did that for a
few years. and then I started, about ten years ago now, I started this company
called Mott MacDonald and they had brought me in, as an IT manager, with a focus
on that CAD kind of world. and that was my kind of first foray into management.
Right. And more strategy and more strategic thinking and the more diverse I.t
world. Right. I had exposure to that, at the firm in New York as well too,
because I would work hand in hand with help desk, people, right. So a common,
thing that we would face is, somebody having trouble with their computer and, it
could be the software, it could be the hardware, it could be a number of
different things. And we would work closely together with the help desk people
to kind of determine what the kind of root cause of some of those problems were.
so when I transitioned to Mount MacDonald, those are kind of brought me in for
that expertise. and it was four hundred person IT company. and that was the
first time I'd been a part of a big company and a big IT team. and it was a bit
overwhelming at first. knowing who to talk to, where to go, where to turn, and
kind of an eye opening moment for me. about a month into my position there, I
see these tickets coming in, regarding CAD and things that I have solved over
the years, hundreds of times I could do it in my sleep. And I remember going to
my IT director at the time and saying. should pick up these tickets, keep in
mind there's a four hundred twenty four hour service desk, local help desk,
workplace team. but I'm seeing them come in. I'm not seeing them being picked up
and I'm like, should I just pick these tickets up and do them? And, he said
something to me that really kind of hit home. and it was a bit of a shift in
mindset for me was, he said, you can, but be careful what you wish for. because
if you do, those people will come to you forever and ever. but instead, is train
the people that are underneath you train the local workplace team on how to pick
up these tickets, train the service desk, the L1, L2 teams on how they can pick
up some of the easy quick wins, and then train the local teams and work with
them and be a support for them and guide them and train them. And that really
kind of like was an eye opening moment for me. going into more management.

Mike Kelley: Yeah. And actually, I think that's, out of all of the interviews
I've done, you're the first person that has verbalized that well, in that sense
of, it's so much we have that analogy so much like with the help desk, when the
help desk teaches somebody how to fix something and instead of just saying,
here, move out of my way. yeah, then that user learns how to do this, but now
you're talking at it at a different kind of level. And I've never heard anybody
else verbalize it like that. And so I think that that's a key point for any of
our listeners right now who are trying to make changes in the ranks and move up
the ranks, help teach those to do that for you instead of taking it all on
yourself. Because in doing that, you teach them, they become more valuable and
you begin to lead, which is where, we left off. You starting in the management?
Keep going.

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