
Phil Howard & Jim Harden
Short Clips
Jim Harden
Jim Harden began his IT career in the Marine Corps, building tactical data networks from commodity gear before moving into corporate technology and leadership. Now CIO at Singleton Schreiber, Jim joins Phil Howard to explain how IT can move from break-fix support to business strategy.
He shares why his team is giving lawyers one governed entry point for AI workflows, how infrastructure as a service cut new-office deployments from days to hours, and why growth requires two- and three-year technology plans. Jim also explains what he wants from specialist vendors, including a project that consumed about $40,000 before being scrapped, and why a strong project manager can be worth every penny. The conversation closes with lessons from bad leaders, useful feedback, humility, and the questions Jim asks at the end of every one-on-one.
We review circuit consolidation, contracts, security, outage visibility, billing, and future flexibility to reduce chaos without forcing change.
Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.
[02:15] Jim traces his path from tactical data networks in the field to a corporate network serving more than one million users and then into leadership.
[07:29] Legal IT has little room for compliance mistakes, but the team still needs room to solve business problems in new ways.
[10:01] Jim explains why the firm is investing in one tool, then building workflows and agents around the work lawyers need to do.
[12:37] The firm puts as much effort into education as platforms and uses its technology committee to test each request against a real problem.
[14:58] Jim describes using the firm's Microsoft environment and vetted privacy terms to reduce the risk of sensitive information reaching public AI tools.
[17:49] Jim expects companies to choose a platform first, then let the work determine which AI model runs underneath it.
[21:10] A seat at the table gives IT the context and voice needed to shape system decisions before contracts and operating choices lock the firm in.
[26:26] At Singleton Schreiber, Jim was asked to build plans for growth, onboarding, offboarding, AI, case management, and other enterprise needs.
[28:43] Infrastructure as a service, drop shipping, and local contractors helped the firm reduce new-office infrastructure work from days to hours.
[29:39] Jim prefers vendors that do one or two things well and can provide clear ownership when a serious issue needs immediate attention.
[36:19] A licensing provider accepted a complex development project, passed it through subcontractors, and left the team with work that had to be scrapped.
[42:21] Jim explains why every one-on-one ends with a request for honest feedback and why leadership growth has to continue inside the C-suite.

Phil Howard: Everyone out there listening. We're speaking with Jim Harden, CIO
at Singleton Schreiber. Give me just kind of a little background, man. Like, so
what do you guys do? How'd you get started? What was your first computer? How'd
you get into this wildness?
Jim Harden: Yeah. I mean, like, my, journey into, it, started back in my
military career, believe it or not. So it's, started off, as an enlisted guy
going through boot camp became a tactical data networks, guy, building. tactical
networks out of commodity type gear out in the deserts. Right. and, that was
kind of my forte into really what led into more of corporate i.t coming out of
the Marine Corps transitioning into a corporate job. I ended up working for EDS,
which was a, they were at the time building. Nmci. it was the largest
privatized, government network or contract at the time. So privatizing the
entire data systems for the Navy and the Marine Corps. so it was a really
interesting brush coming from, a couple of guys setting up tactical data
networks in a field to, a user base of a million plus, at the, on the corporate
side. and then then from there, I had a lot of really great, mentors coming
through the military and everything else that encouraged me to continue my
leadership journey. and really ended up, starting to get more interested in the
leadership side of things than the, engineering side of things. And, although I,
cut my chops as an engineer and kept my skills up to snuff, really moving into
leadership and mentoring people from my side was much more appealing to me. and,
the legal industry is something that, I never dreamed I would be a part of at
some point. Like it's not one of those, industries that you, you know, if you're
going to be a lawyer, great. from the it side of things, it really is just like,
hey, what's, like I said, it's kind of, it's a little bit of an industry that
time had forgotten.
Phil Howard: yeah, well, first of all, the amount of people that are in IT
leadership now that were in the military, I mean, it's a good twenty percent of
the people that have been on the show. So I don't know what that is. I don't
know if it's the discipline. I don't know if it's the, calm under fire. I don't
know if it's the I can take a thousand things and still like projects and crap
thrown at me and still be calm and deal with that and still lead through that.
Maybe it's that, I wasn't a marine or I wasn't in the military or anything, but
I know that there's like a test that someone takes somehow and they're like,
okay, like you're really dumb. So you're going to peel potatoes and we need
potato peelers. That's like kind of like the joke, right? And how did you end up
there?
Jim Harden: Yeah. I mean, so when you kind of go through the recruiting process,
you take that, it's called the Asvab test, you take that and that that really
kind of gives you what your competencies are. And then based on what the
military or the whatever that branch needs at that time is what they, start,
plugging holes for, they have a whole planning process of, we're losing, six of
these guys, five of these guys, we need to, recruit to have these particular,
spots filled. Right. And, initially I did not get in, as, what I wanted for the
field data technicians because, actually there's a lot of requirements. And one
of them is, you have to pass a color blindness test. I failed that I had to get
waivers. I had to.
Phil Howard: Like every guy, you guys or something fail that. Yeah. Yeah.
Jim Harden: Well, and then so then my option was like, hey, if you're not going
to do data, we're going to put you as a weapons instructor because you can see
black and white on the targets, right? So, I ended up training as a, small arms
instructor, while I was waiting for my, waivers and stuff to clear, to become a
field data technician, which ultimately, it did.
Phil Howard: So sweet. I really love one of these subjects that we're supposed
to talk about today, which is building an IT culture that thinks outside the
box. And it's so important, I think, in any small IT department, because each
little IT departments kind of like their own business or their own
entrepreneurial kind of thing that needs to figure out how we don't speak in
ways that are just like super technology and glaze people over. And then we
don't just show up and do a job every day because with the way the technology
changes so fast, you just can't do that anymore. You can't just be like, I'm the
network admin and I'm going to only do this forever. And I don't know if that's
what you meant by when we talked about thinking outside of the box, but how do
you get a technical, maybe engineering minded technology person that has
blinders on that only sees things? Maybe one way to think outside the box?
Jim Harden: Yeah. I mean, it's by nature for it, right? That we've spent so much
time trying to be inside box and work within parameters. When you come to
compliance and certain things where it's like it's very black and white, right?
And that's where, I think that anytime you're sitting within some type of
framework or, certifications or things like that, again, they're very kind of
like, they're almost to the point where they're restricting, having the ability
to use the creative side of your brain is not always something that's been well
received in it. Right? Because it's, those are the types of things that, hey,
well, we're going to try this just to make it work and you may end up taking
yourself out of compliance. Or the million things you haven't considered. Right.
And I think that, when we think outside the box, as far as large scale
solutions, it's about how it can be a business partner rather than a cost center
with the business. Right. So, most of the time it has a budget, you're spending
our money, you're keeping us compliant, all these things. Whereas like, more of
the out of the box thinking these days is how can I provide value to operations?
How can I provide value to marketing? How can I provide those types of things as
I t when we're supposed to be, fitting or coloring within inside the lines, so
to speak. Right. So it really takes a company or a firm. that is progressively
thinking enough to allow you to have that seat at that table because, again,
like this podcast here. That's why it's sparked my interest. You've Been Heard.
There's been so many times within my career, where, not only did, were we not
heard, but didn't want to be heard from. So, now I feel like with the deep ties
to everything that we're putting out as platforms, whether it's AI, whether
it's, newer, case management systems or things like that. the business wants to
hear from us and hear our thoughts and hear creative ways to, actually make a
problem go away. Right? and it's been a balance because again, you always have
to operate within, compliance and things like that. in the legal industry,
there's not a whole lot of gray area. it is or it isn't. So, we have to still be
mindful of what we do, but we also have to not just, fit inside a framework all
the time.
Phil Howard: Any tricks to getting the staff to kind of open up or think outside
the box or maybe connect with, lawyers who might not be the easiest people to
approach or might be a bit intimidating from time to time or expect things done
in a certain way. This is me completely stereotyping them, I don't know.
Jim Harden: Yeah. I mean, so lawyers are always looking for creative ways to
bring, information and cases to court, right? So they're looking for things
that, again, the letter of the law is black and white, and there's no coloring
outside the lines. but there's ways that to go about things. And I think a lot
of it has to do with the kind of culture you create, because you had mentioned
that, how do you do that from a culture standpoint? And a lot of it is, just how
you approach, making sure that your team is heard and that their ideas are not,
just because you sit in this role doesn't mean that you can't come with a great
idea on how to solve a problem, even if it's a very, very complex problem,
because you might ignite a spark that, lights a fire and we're able to get, go
off to the races. So a really good example is, just, coming back to kind of AI,
everybody wants to bolt on AI component to their individual legal tool, right?
So you end up with this entire stack of, AI tools, whether you want to pay for
them or not, because they're all, put together as part of your package. Now it's
all included in your licensing and everything else. everybody wants their own
flavor and there's all the buzzwords. Claude. And then, one lawyer hears it and
then it spreads like wildfire. So what we've done is, we kind of approach it as
our creative solution to the AI problem in legal tech has been we are going to
invest in one tool, and then we're going to work with workflows and integrations
within the tool that actually gives people what they're looking for with the
added capability of having the wrapper of, the context through like copilot or
something, because we're a big Microsoft shop, right? So, people want to use
Claude. they want to use, Westlaw, they want to use Everlaw. They want to use
all these other things. What we want to do is we want to, not shy them away and
say, no, you can't use that stuff because we haven't vetted it. It's going to
take us six months, whatever it is, we're going to create agents within copilot
that are going to actually, perform these workflows that you're looking for that
not only gives you the information you're looking for through those platforms,
but we're also going to have copilot look at contextually, you send an email to
so-and-so about this. You had a meeting about this three months ago. So it's
more of a force multiplier than it is addition.
Phil Howard: Okay. So number one, it sounds like the end users, the customers
that you serve, the lawyers a are a bit savvy. or I guess, or are they using AI
more as a glorified, Google for research. So I guess my first question would be
is, do you have any kind of AI steering committee and broken down that yet?
Like, do people have a way of being educated on AI.
Jim Harden: Yeah. So we've, put as much into, training and education as we have
the actual platforms because that was something that we baked in initially. so
we have not necessarily an AI steering committee, but we do have a tech
committee that we come together and we talk about, these tools quite a bit. and
rather than, somebody coming and telling us like, hey, this tool is great. I
heard it from this guy. Can we implement it? then we, take that step back and
say, okay, what's the problem we're trying to solve for? Right? Because there
are a lot of these things are waiting for problems to solve that we don't
currently have yet, right? So we don't want to fall behind, but at the same
time, we don't want to throw a bunch of stuff out there where we're managing and
having to, look at compliance on all these different, tools, right? So, really,
it was kind of the spark of like, hey, well, how can we make this as simple as
possible? Because there are a lot of lawyers that have an appetite for the
technology and want to use the latest and greatest tech and everything else.
There's also a handful of lawyers that are just as comfortable with a legal pad
and a pen. they don't want to use, all this high speed technology and everything
else too. So how can we best deploy our tools for the much broader user base? So
like at a minimum, these guys are using, they're living in the Microsoft world
because that's how they get their email. That's how they live in word, putting
together, docs and things like that. So the best thing we said, okay, well, how
can we integrate all this stuff then in a copilot? Because if we can give them
one tool that can do all these other things, rather than a bunch of individual
tools where you have to remember to go to this to do that, or, vice versa. that
was kind of the strategy. It just really is, what's the minimum entry point that
we can get into maximizing the value of these tools because again, when it comes
back to an ROI discussion, the lawyer that wants to use the legal pad in the
pen, we want him to use the tools to realize our ROI on this stuff. So we have
to make it as seamless and as simple as possible for them to actually use it
than to try to remember where they have to go. Or, oh, I even forgot this tool
existed, right? Come back to the same place, find your agent and go. that's our
philosophy.
Phil Howard: We could talk about this all day. Okay, so now what about the
security guardrails? What about the data dips? And I mean, there's just so much
for it to just kind of worry about, I guess, or be concerned about how do you
deal with that?
Jim Harden: So that's really the, philosophy and the way that we're doing things
is really because of that, right to set up the guardrails where we have the
control of, whatever these workflows and agents are doing within our Microsoft
environment that are all bound by the same privacy policy that we have with
Microsoft versus waiting. somebody will go out and dump something in a web
version of ChatGPT, and now all of a sudden we've got, anything from client data
to, any type of like, trade secrets or anything else, which has happened. not
necessarily our firm, but we've seen reports of other, law firms putting stuff
into ChatGPT to, analyze and to create documents. And, they're not using an
enterprise product they're using, and oh, I didn't check the box to say don't
learn off of my input.
Phil Howard: And I don't think that I wonder if that even matters. Do you guys
know if that even matters technically, because I think you can still search
every public ChatGPT, even if they didn't click learn off my knowledge, I think
it's still possible to search those strands.
Jim Harden: It was for a while. I don't know if it still is, but I remember it
making pretty big news and I thought they made some changes, but I'm not sure.
Yeah, but keeping it within our walled garden, right. With Microsoft, if we're
providing agents for this stuff, we know it's not because, we've looked very
closely at the agreements. Our in-house counsel is, checked stuff to make sure
that we're not feeding what we shouldn't. And, basically anything that we're
filtering through an agent that we build within copilot, whether it's making a
call out to, another tool or to a AI subprocess or anything else like that. it's
bound by that same privacy policy as Microsoft and we vetted that and we've been
able to test it and know for sure that's the case. Anything else, any new tool
that comes out there and people just start using it. it's the wild West,
Phil Howard: what's your prediction eighteen months from now? What do you think
everyone's going to be talking about that. They're not talking about today.
Jim Harden: what happened to AI, honestly? I mean, all these things that they've
promised, I mean, there's been so much on, that was made of this stuff about
how, again, it's going to replace people. It's going to automate your mundane
day to day tasks and be, again, it's kind of a force multiplier rather than,
adding additional, headcount and the knowledge of people that have been in the
industry for a long time. I mean, you can't, train an AI model to have twenty
years of legal experience. They'll tell you like, hey, well, this thing's
constantly training. It's going to know it. But I mean, there's seasoned trial
lawyer who's been in the courtroom for twenty plus years. it's like you're not
going to be able to replace anything like that. An experienced paralegal that
knows exactly how to work with their attorney. from just a cultural and a
communication standpoint, AI is the big shiny thing, but the bubble's going to
burst. And, the, people aren't realizing the, revenue coming from it that they
thought they were going to.
Phil Howard: Tokenization is going to be an important one to weigh out. I mean,
there's so much to kind of break down there.
Jim Harden: I say this a lot to some of the folks around. It's kind of like when
you go buy a car and you pick what engine you want in it, you want the six
cylinder or do you want the upgraded, V8 or do you want, I think it's going to
be that where, like you said, the tokenization is you're going to pick your
platform and then you're going to pick your engine like it's not a this or that
or all in or all that because I'm starting to see the way that Microsoft is,
marketing copilot and the way that they're building it out. And, going forward,
it's they've integrated co-work with Claude. Where you again? tokenization
there. It's not you're not dealing directly with Claude. You're dealing with
Claude within copilot, same with open AI and, all these other things.
Phil Howard: That actually scares me. That part. And the reason why that scares
me is because it happened to us. So we were using Claude and whatever, open claw
or whatever, right? Not to be confused with, like, Claude and built out like a
pretty big model, based on that. And then, literally overnight. It was just sunk
because Claude, shut down the, open claw like tokenization, whatever it was, I
can't remember. It was Greg would know and be able to speak to it a lot more
than me. but literally overnight, it was like, well, that sucks. It was like an
entire production. All of production was like, just shut down like literally
overnight. And it was like, okay, we've got to now, okay, we gotta take five
steps back, break this, break that, and then rebuild this and go back to this
way. That scares me. and it was bad for us, but we're a team of, what? Ten what
about a company with two thousand end users or a million or something that's
just like, it would be like, it'd just be bad. It'd be, it could be really bad.
Jim Harden: That's why we're more investing into the workflows and the tools
because if we get too heavy into a particular tool. Yeah. like you said.
Phil Howard: Focus on the instructions, focus on the skill sets, focus on the
skills, the instructions, how you build it out. yeah. And then if you can share
models like if we can build the agent and then have that agent pick the model
that you want to run off on any given day in a secure single source of truth
that does not access the outside world through a wholesale, type of, great.
Jim Harden: Yeah. That's exactly what Microsoft's doing in their model. I mean,
if you look at how their copilot config is and some of their AI, subprocessors
that you can, add to your Microsoft tenant. if you look at like the researcher,
agent within Microsoft, you can select, I want ChatGPT or I want to claw this
version or whatever it is, you can select that, but most of them are defaulted
to auto where it's like, hey, well, I'm going to understand what the request is
first, right? and they're going to pick that apart and figure out what's the
best model for them to use? It might be the copilot model. It might be OpenAI,
it might be cloud. So Microsoft's doing that. And I think that's going to be the
future of this stuff is like you said, it's it's really like.
Phil Howard: Of their empire to continue.
Jim Harden: Yeah.
Phil Howard: All right. Okay. we have something to talk about, which is no seat
at the table to driving strategy. because the stats out there are that ninety
three percent of IT leadership, does not think of their team as executive
management or the round table. They think of their team as the help desk. They
think of their team. This is my team. These are my guys like this is and then I
got promoted. These are still my guys. So I don't know if that has any fits into
like no seat at the table, the driving strategy. But what do you mean by that?
Jim Harden: Yeah. I mean, where I came from previously was very much like you
just said, like, hey, out of sight, out of mind. Just fix things when they're
broken. And, we had great ideas and we had great people. We had great minds, in
those seats. but just no platform and no voice to express it. And, when you get
into a situation where it's very kind of closed off at the top and there's just
not a lot of communication back and forth. you're flying blind and a lot of
decisions are made, on systems and everything else at an operational level, not
having that seat at the table, which is, again, valuable as a business partner
rather than just being, a utility or a cost center. Right. and as much as, we
try to, raise our hands and say, hey, we've got some really great ideas on how
we can do stuff here. it was always just fallen on deaf ears. Right. And, I
don't know how you break through in those types of scenarios other than, move to
some place that's going to actually listen to what you have to say, right?
Because you could do it till you're blue in the face and you just build a level
of frustration where it's, I want to have some creative input on this stuff and
figure out how we're going to move forward. but you got, operations and bean
counters that are, making decisions at the top based on, oh, well, we signed
this a bad contract or this then we get pigeonholed and we can can't do anything
about it. Right. So, really my move to Singleton Schreiber was, along the lines
of the conversations I had with everybody there from our, managing partners to
our executive team, they were very much saying, we want to hear what you have to
say. We want you to drive the ship. which is you always take it with a grain of
salt because that's what I was told previously too. Right. And we, never got
there. so coming in, it's been a breath of fresh air and really just, being able
to, kind of temper like I had all these things, all these great ideas. And I had
this great plan that I put together and everything else too. Well, now you're
stepping into some place that's brand new. You got to temper a little bit of
those expectations and say, okay, well, there's a lot like, what don't I know?
And as you're taking that information in, then you're starting to develop your
longer term plan.
Phil Howard: Just a little bit of background though, just a little bit of
background. You just started at a fairly large law firm as their first ever CIO.
Jim Harden: Correct? Yeah. And the firm I was at previously was the first time I
was actually with a law firm directly, and I was at a director level there. So,
I again, I never thought I would be into the legal industry, but, I worked for a
company where, I had a compliance and security became a big thing. And I worked
directly with their legal teams quite a bit. and I found that both, interesting
and fascinating, so I said, well, shoot, I had a really good time working with
those teams. why not? try for a law firm. Right. and I'll tell you right now,
defense law firm versus plaintiff law firm, they're completely different worlds.
So, they're almost a different industry really. you deal a lot with the same
tools, but it's just the cultures, the attitudes, the leadership and the
direction that you go and those, different sides of the aisle it's crazy how
different they are.
Phil Howard: Some industries are definitely easier than others. Some industries
are more prone to it as a cost center. however, I do think. It's this is never
supposed to be about like it versus like the C-suite or the C-suite versus it.
It's supposed to be. That's the whole point of You've Been Heard. It's supposed
to be like, hey, we hear you C-suite, or we hear you executive management and
like, you hear us, we're all like, like together trying to bring the business
forward to what the ultimate goal is. And a lot of the problems that I deal with
is a breakdown, or a lot of the complaints that it have is a breakdown of that.
And so if you hear someone that has like, we have thirty projects we could never
possibly like, finish them, it's because there's no strategic seat at the table.
There's no strategy. It's like, well, how does this project fit in to here. How
does this fit in? How is this actually going to drive revenue? Back to your
point about ROI earlier, is it even worth doing this AI project if there's no
ROI on it, we could just hire five more, data analysts or whatever, three more
humans that could actually do it physically better, faster and, more personable.
So if that makes any sense, that stream of consciousness.
Jim Harden: Yeah, yeah. And I'll tell you, I mean, I have definitely have that
seat at the table. I have the voice. I mean, my, executive team at the firm and
the partnership are huge. They couldn't be any more supportive of what we're
doing. because they know that we're there to help and partner with them, rather
than to be, dictators, driving solutions down people's throats. we want to make
sure we're, listening and we're coming with solutions rather than just products
to,
Phil Howard: So whoever that is, I would like to give them a high five and a
standing ovation. I would love to have them on the show and actually have them
say why we, are a pro technology like whatever it is. And it would be like,
sitting in like an Amazon meeting with Jeff Bezos. And he's not a proponent of
it as a business force multiplier. I'd be a complete joke. if you had to put it
in like one sentence or something? Like what did they say they wanted from it?
Or the relationship around this leadership kind of like structure and
everything.
Jim Harden: I mean, I can sum it up in one word and it's strategy, because
again, there wasn't a whole lot of strategy and, strategy was probably being
driven by, more operational and everything else where, I think there was a
realization that, everybody's asking for these new tools. And again, the
technology in the legal industry has, literally exploded again, there hasn't
been a lot of like forward thinking or a lot of, tools are built on prem old
legacy, relational databases. it's just very, very old school, right? So now all
the forward thinking and seeing and plus, the growth of the firm too. That's the
other thing too, is that the growth also pushes forward, the hunger to innovate
and how we do things better because as we're doing more business and we're
opening more offices, I mean, we can only throw so many people at that right
before it becomes, an issue.
Phil Howard: So when they say strategy or when you say strategy, but we want it
to help us do X so that we can deliver Y as a business. I'm assuming it's
something like that.
Jim Harden: Yeah. we're paying one point three million dollars a year for a case
management system because like they're, best in breed or something like that.
Like, hey, is that the right decision. there's new things on the horizon. we
keep hearing about AI. what's our AI strategy? Everything is what's our growth
strategy? What's our, onboarding and off-boarding strategy, what's our AI
strategy? Everything would need to come down and we needed to make strategic
decisions and actually build out, two, three year plans for, our strategies
because again, it's kind of just growing, growing, growing, and, unless you
strategize it's going to eat you up. And, my first year here, but front of mind
when I first came in here was what strategy do we have? And then as the firm
grew, it was more, instead of piecemeal, like, how can we put an enterprise
solutions and things that are scalable and build to growth as a platform and a
solution rather than, oh crap, we just acquired some business in another state.
Now we need to turn everything and ramp up and, add more stuff, right? we just
want to scale up. We don't want to necessarily just keep throwing,
Phil Howard: Money versus reaction. So responding to it versus reacting to
things that just kind of blow up and, the old break fix mentality.
Jim Harden: yeah. And again, strategy being important is, we've opened up a
handful of new offices around the country and it's, we've gone from deploying
those things in days to deploying them in hours, with infrastructure as a
service with, outsourcing certain things. So again, our strategy before put a
bunch of people on a plane, order a bunch of gear, get down there on the ground,
put it all together, everything else. Now, with the miracle that is,
infrastructure as a service, we build this stuff out, we drop ship it there. We
have a contractor show up rack and stack, and we're off to the races.
Phil Howard: So when it comes to dealing with the plethora of vendors, CSPs,
vars, technology solution distributors, all of these people and the new, influx
of, AI stuff that's out there. What is your single biggest frustration problem
or concern as it pertains to that model of, I guess selling.
Jim Harden: I think a lot of it is, there aren't very many vendors that I've
seen out there that can be, they try to be a Swiss army knife and do a little
bit of everything. And it's always that inch deep, mile wide. And I'm okay with
a vendor that does one or two things really, really well. I don't need you as a
vendor to do everything. Like give me what your best, business model is and what
is it that you're known for? And, we just had a meeting with a big, national,
hardware vendor, last week. And, they showed us a slide about how we've acquired
all these companies and we do all these things, right. our conversation with
them is like, look, we're focused on getting this part right with you guys. And
then we can have discussions on the other parts, but we don't want to sit here
and talk about how this could be an all encompassing solution like show us first
and then we'll have additional conversations because, we've got a vendor for
this or that or everything else, and we've got two years left on our agreement.
Right? So I'm happy to come back to the table and talk to you about it, but
let's get something in place first. And don't pitch me. the entire playbook,
right? give me one running play and one passing play that's going to hit every
single time. And then we can start talking about expansion from there. I think
that's the biggest thing is that, it's a great idea to have that one vendor that
takes care of all these different things, but it's like, how good are they at
each one of those things, right? That where you really have a need. I'm okay
with having two or three or even four really good vendors that do one or two
things. Great.
Phil Howard: I can tell you that to do like a really good telecom project, if an
I.T. guy was doing it by himself, and if he was like evaluating all these
vendors and he went to that guy, in reality, it could be a nine month project.
And there's no way that someone can just add that on and that they know about,
everything to do with every pots line. and, just porting numbers and operations
departments on that day and just every possible thing that could go wrong with,
a large group of end users. And I'm just trying to think of the snapbacks and
just like, how you map out auto attendants and IVR is and now point solutions
with, skills based routing and all these different things. and then on top of
it, it's like how many people actually have, any type of legal experience with,
FCC rules and regulations and what's allowed. And most people don't know that,
like a ninety nine point nine nine nine percent SLA is kind of a joke because
it's a geographical downtime over thousands and thousands of customers. So any
company with a thousand customers is going to have a ninety nine point nine nine
percent SLA. so there's like a lot of these kind of like dumb things. yeah, to
your point, you can't be everything to everyone. That's why.
Jim Harden: I don't want my circuit provider trying to sell me Microsoft
licensing and security services. I don't want that. But but they try to all the
time. But I mean I don't want them managing my Sentinel instance in my Microsoft
tenant. If you want an edge firewall, fine. but I'm not going to wrap up, all
that spending with Azure and, Microsoft three hundred sixty five and all that
stuff to like spectrum, I'm not going to do it.
Phil Howard: there's no way that they're going to be really, really good cloud
desktop designers, right? Or, some real niche, like real niche kind of
healthcare, azure cloud desktop design. And then, it's just like you need the X,
submarine Navy guy that works over at whatever Microsoft company. Now that's
really, really good at that. I just there's so many submarines. Guys, I don't
know why submarine Navy guys that are good with desktop design and Microsoft,
but for some reason I know two of them. It just seems like you're also a
submarine guy that was underwater for this many months. I just think it must go
hand in hand with like, you know, fires and subs underwater and stuff. so. But
the other thing that you kind of said is that whole Swiss Army knife approach.
And I just kind of wanted to dig in a little bit more because what that tells me
is that they care more about getting paid in any way possible than they care
about delivering you a specific solution for a unique company with a unique
group of end users. And to me, that vibe is not the vibe that's going to vibe
well with my IT department. I don't know if you agree with that or if you've got
any deep thoughts on that, but that's from when you said Swiss Army knife
approach. I just heard, dude, we just want to sell as much as possible and hit
quota and appease investors. And like, that's what my job is. And what I've
heard from other guys is they say, well, we just do all the research ourselves
now, and then we go to the CSP and just say, hey, sell us this stuff. And to me,
that's like a unwarranted gift to them.
Jim Harden: Yeah. and don't get me wrong, I mean, the Swiss Army knife can be
useful in certain scenarios, right? And there might be customers that are, well
positioned because obviously if they're selling it and they're making money off
of it there's somebody out there that's willing to buy it, when it comes to more
enterprise and, holding vendors accountable for things, we can't have a single
account executive that we reach out to when we have a cybersecurity problem
versus laptops didn't show up at a particular office. Like that's just not,
weird, right? And when I make that phone call, I want to talk to the CEO of our
cybersecurity company to say, we've got a major problem. I don't want to call
account executive for, a Dell or a CDW or something like that and say, hey, we
have a cybersecurity issue. Run it up the chain to whoever it needs to go to.
Right? Like I need help and I need it now. So let's figure it out. so that's
where, having, the compartmentalized, pieces of that and, it helps with the
accountability as well. So, and then, there's inevitably you're going to change
vendors for things when they're underperforming or everything else. what if one
piece of this is not working out, right? you have to pick apart the whole thing.
You have to have a new agreement, new contracts. And, hey, if my, hardware isn't
working out. Cool. There's five other places I can go that do hardware, and I
know that they do hardware right now. If it comes up to a solution that we don't
know anything about, like, hey, we're kind of dabbling into this. We don't have
the in-house expertise for any of this stuff. we have those people that we can
go to also and we work with a boutique firm here for cybersecurity. that's based
in San Diego and everything else. And they're really great at telling us what
they're good at, but they're also really good at telling us what they're not
good at. And when we call them and we say, hey, let me bounce this off of you.
Hey, I got somebody else. let me put you in touch with them. rather than saying
like, hey, we got this project quick, let's go hire a guy and make it happen for
him like that. That never works out. I've been in that situation a handful of
times. It has never worked out well for us one time. So,
Phil Howard: Please give me an example.
Phil Howard: Real quick. I got to know that example just like a real quick. This
never worked out and this is how we did it.
Jim Harden: Yeah, exactly. we had a firm that was, acting as our CSP for a lot
of our Microsoft licensing. and then, this is still back. We had some stuff on
prem. This was years and years ago, but we said, hey, we need to build out a
new, intranet within SharePoint. We have to integrate it into ServiceNow. And we
have all these like things that we want to do. And they're cool. Yeah, we can
totally do that. nowhere on their website did they say that they were in any
type of software development. they sold SharePoint licenses. They didn't build
SharePoint sites. Right. And these were very complex things. So it's, hey, well,
we got a guy and it was a sub of a subcontractor or something along those lines.
And I mean, I can't remember, I think we were about forty thousand dollars into
it when we said, no, we're done. We went out and found like the premier,
SharePoint, developer that we knew of in our area. And, we ended up not only did
we end up eating the forty K, we only ended up paying them, I think, marginally
more to actually get it done right the first time, but it had to be scrapped
completely. So it was a waste of money. It was a waste of time, was a waste of
resources. And it actually put a strain on our relationship with that vendor to
say, you told us you could do this, what the hell happened? Right? So I'm more
willing to take the advice of a vendor that says like, hey, we don't do that.
But let me put you in touch with somebody that does tell me what you're not good
at. I know what you're you are good at. Tell me what you're not good at and how
we might be able to, get put in touch with somebody that can help us out.
Phil Howard: Average IT project cost overrun twenty seven percent.
Jim Harden: Well, I'll tell you what.
Phil Howard: What oh no no one in six projects become a black swan with two
hundred two hundred percent overruns,
Jim Harden: I'll tell you what having a good project manager is, worth every
penny that you pay. when you find somebody that's good because that's one of the
additions we had added to our team here recently is that we had a ton of
projects. We had a ton of stuff to do. We had a ton of talent. we had engineers,
we had vendors, we had everybody else having that project manager to avoid any
type of scope creep or overrun, has been incredible for us. And, you look at
some of the costs of, sometimes a PM or something like that, and you kind of go,
oh this person's too expensive. you almost can't afford not to have them when
you're doing a lot of projects.
Phil Howard: More IT guys need to say exactly that. And they need to say that to
executive management because, and this is the way I think we should say it. And
this is, oh, man, I'm so glad you said that. And one of the biggest
underestimated investments in business is just paying a lot of money for the
right person.
Jim Harden: Yeah.
Phil Howard: Because that one person could like just skyrocket, like production
and streamline like X, Y, Z and bring the company to the next level. It's like
the Netflix story, right? Like what did they do? Rather than hire like three
hundred developers, they just went and cherry picked and like guerrilla
recruited like the absolute best dev guys in the world. And they're like, we'll
pay you ten million a year. Like they're getting like five hundred thousand a
year or whatever. We'll pay you ten million. you know what I mean. It was like,
let's get ten of the absolute best ninjas in the world rather than hire like,
three hundred people and end up with a bunch of broken code. This is my
understanding of that story. Someone else probably knows better. Last question.
Jim Harden: Yeah.
Phil Howard: You go back in time, you have one piece of advice to give your,
younger, more ignorant self. what would that piece of advice be?
Jim Harden: So I learned a lot from some really good mentors. I've learned even
more from bad leaders that I've had in the past. so as you're getting frustrated
and you're saying like, I can't believe that they're doing this or, you start
feeling, anger or you start, I'm going to rage quit or I'm going to, rage apply
for jobs on LinkedIn after a bad interaction. Take that as a learning moment.
And because when you land in your next spot, you can emulate great leaders. What
it's more important to not do the bad habits that you've been exposed to in the
past. That's the biggest piece of advice I would give to any young leader in it
these days. There's so many people out there that are, managing it that don't
know or haven't been in the trenches and haven't had that experience. it's
terrible. And, it creates a lot of frustration, but use that as something like
that's going to make me a better leader in the future to like, I know what not
to do just as much as I know what to do.
Phil Howard: It's a really, humbling, kind of question and It's like, when you
think of the worst experience you've ever had from a boss, what experience and
memory came to mind? And we will end with that. Don't do that to other people.
Right. It's like I can think of a few.
Jim Harden: and it's, you know what? In the journey of leadership, you got to go
through those things. I mean, that's, the thing is like, nobody that's ever
mentored me or anybody that I've looked up to as a leader has ever said, like,
it's been such an easy path to get there. And I just grew as a leader, like you
have to walk on the coals to understand that they're hot, right?
Phil Howard: And so many cry myself to sleep nights back in the day, I think it
was more than I think it was more the retail restaurant days.
Jim Harden: and if you don't go through that, like if I never went through any
of that, I would never be here. Right. So that's the way I have to look at it.
Phil Howard: the VP of Starbucks at the time, who became the VP of like whatever
coffee and tea company, he gave me a book first break all the rules wrote in the
front of the book. He said, Phil, do this. And, in the book, there's an exercise
where you take your whole. And I've talked about this on episodes before. You
take all of your team, whatever it is, employee group, whatever it is, put them
in a room, lock them in a room, put one person in charge and have them all go
around the room. and there's like a series of questions that they ask that the
leader asks about you. It's completely like, I'll never know who said it. I'll
never know. Whatever. It's like all feedback. It's like, what do you do good.
What do you do bad? What do we need him to stop doing? What was this? All that
right. And then that one leader in the room takes all of that information and
types it up in an anonymous like report and delivers that to you. That's a
humbling experience. But you have to be willing to do that. And I think a lot of
people might not be willing to do that.
Jim Harden: Humbleness is one of the main leadership traits that a lot of
people, don't realize and end every single one of my one on ones with everybody
on my team as what can I do better for you? What am I missing? The mark on? what
would make me a better leader for you? I ask those questions at every single one
on one that I do, because you have to maintain that humility and that
vulnerability. Otherwise, when you're in the C-suite, you're not looking at any
more promotions. So your growth has to be within yourself and within the way
that you lead. that's how you have to take it.
Phil Howard: So yes, been an absolute pleasure having you on the show. And thank
you for your time. And, You've Been Heard.
Jim Harden: I appreciate it. Thanks for hearing me.
Phil Howard: Everyone out there listening. We're speaking with Jim Harden, CIO
at Singleton Schreiber. Give me just kind of a little background, man. Like, so
what do you guys do? How'd you get started? What was your first computer? How'd

You’ve Been Heard is where IT leaders stop being sidelined and start being amplified. We’re the triple-threat platform: podcast, community and vendor-neutral advisory that elevates your voice, your value, and your influence because when IT leaders rise, so does everything else.
© 2026 You've Been Heard. All rights reserved.