434- AI Hype Needs A Business Case w/Tim McCrosson

Phil Howard: So Tim, let's start off with this. I mean, if you have any deep
thoughts or feelings right there, like go for it. But I definitely want to hear
what your first computer was and how you got started out in this whole thing.
And give me kind of like the short story, how you got started in it and how you
ended up where you are today.

Tim McCrosson: Yeah. So I started in it during the dot com build up. Building
websites and eventually got into a contract building websites for housing and
urban development of all places. And this is just during the dot com build up
years and which I think quite frankly, is very similar to the environment that
we find ourselves today with respect to AI. Right? So back then, in the very
early years of websites, you had these, I like to say, flaming candelabras that
were on like the different websites at the time. AltaVista was the leading
search engine for good reason because they did it right? But Google figured out
a way to more effectively monetize their search algorithm and actually make
money off of it, whereas AltaVista just had the really good product. They didn't
figure out how to make money off of it. Sad. So yeah, anytime you do something
well, people sort of ask you to do the next thing. And so it went from websites,
web development, ColdFusion development, and then to project management. And so
I was running redevelopment of big grant systems at HUD. And for me, it was a
pivotal moment. I was blessed to have the right supervisor at the right time
telling me exactly what I needed, which was that I was completely successful as
a project manager, but I would be completely unsuccessful as a human being
because while my projects were all successful, delivered on time, on budget.
Nobody wanted to work with me afterwards because I was just too hard to drive.
And so that was a really good lesson for me to learn at the time. And so
eventually I changed my course, I changed, I very specifically changed how I
handle people. And I went from being this sort of command and control director
of projects to being more of a facilitator, collaborator, and especially a
coach. And when I did that too, I found that I created a much more sustainable
environment.

Phil Howard: Yeah, it's a hard lesson. It's kind of like, but worthwhile. Yeah.
It's like I have expectations that need to be met for excellence and all of you
should also rise to the occasion of my expectations with me demanding them,
which you kind of learned, like the leadership piece that you want people to
actually want to join your parade and follow you, not just get in the parade
because you have to.

Tim McCrosson: The inspiration, I think, behind that, well, at least part of the
inspiration behind that thinking is Harvard guy named Daniel Goldman, who did
all of the the work on emotional intelligence. And he had, I think, a really
good book at the time, which was something about developing leadership traits
and trying to figure out the leadership styles. The people who are the most
successful are the people who have mastery over a wide range of leadership
styles, because sometimes you need the coach and sometimes you need the
authoritarian. Sometimes you need a facilitator, and sometimes you need somebody
that's just going to collaborate with people. And so the best leaders are people
who match that leadership style to what the team needs in order to ultimately be
successful.

Phil Howard: And I think someone said this way to me one time, like if you've
got someone who's bucket is really full, they've always been crazy successful in
the team. They've got the most wins. I guess like they're probably more apt to
get the more frank, let's push you forward leadership role at that point versus
the guy who's bucket is empty and is brand new and is making mistakes on
everything. You can't be as hard on him as you would. Maybe the the guy who's
bucket is full.

Tim McCrosson: Yeah. Well, for me, this whole process came full circle, Like
probably seven or eight years later when I was put in charge of managing a
project that was very, very high visibility and had input from many different
departments and agencies. And so there was a presidential memorandum that said,
basically in ninety days we're going to deliver this big thing. And so I was
doing exactly what I had done, which was create that collaborative environment.
And I'll never forget this. At the time, he was the CFO for the Department of
Commerce. His name was Scott Quayle. Great guy. And he pulls me aside and he and
he says to me, he's like, look, man, I know what you're trying to do. you're
trying to get everybody to rally around and build momentum. But quite frankly,
we only got ninety days here and we need somebody that's going to get in there
and actually start cracking the whip so that we can deliver on time. And so for
that, for me, it was like, oh, I had spent the last seven or eight years trying
to be Mr. Collaborative, and I had really gotten away from and not used that old
tool that I used to use, which was, let's go and set some direction and hold
people accountable and try to get things done that way. And so it was fun and
interesting to go and pull some of those old skills that I hadn't used very
frequently back into my repertoire.

Phil Howard: Why did we use the word why flaming candelabras? Is it because
everything was on fire and there was just on different.

Tim McCrosson: You don't remember? They used to have these animated GIFs or
GIFs, depending on where you come from. Right? Animated GIFs on web pages. And
they were like these candelabras that were animated and flaming. and by two
thousand and one, two thousand and two. Everybody sort of looked at that as, oh,
it's the tackiest thing in the universe. Who would ever do something like that?
But we all knew that we had. What is it? Excite web pages and things like that
that we had built. And we put those animated GIFs on them.

Phil Howard: So let's go a little bit deeper into like, if you had a moment in
your career where it was the absolute hero, where if your team hadn't been
there, the whole business would have been on fire and come to a grinding halt.
Can you think of a very explicit story?

Tim McCrosson: Well, there's certain times, maybe not a grinding halt because it
is a big government, but people sometimes get they complain about, well, why
does the government do things like that? Why is it so inefficient? Why do you
have so much fragmentation? back in my time when I worked at the white House for
a while and we had this collection. It had one thousand data centers and
thousands upon thousands of separate acquisitions for the exact same software. I
remember one of the worst cases was mobile devices. You know, at the time it was
AT&T, Verizon and T-Mobile has it. Maybe sprint. And so one agency, we had more
than four thousand separate contracts buying mobile devices just at one
department. And it's like, why is this government so inefficient? Why don't we
go out and achieve those economies of scale? And I have an answer. The reason
why, and this is my sort of you've been heard moment or story. because none of
the CIOs during those times had the authority to actually put their foot down
and say, no, I'm not going to let you want that. You're going to have to buy it
in a manner that's consistent with our enterprise architecture. You're going to
have to buy it as if we're for one government for once.

Phil Howard: How would that work, though? I mean, that's the whole like the
answer to your question is the government. Right. but it's a two party system
that switches every however many years and all of the personnel and everything
inside, and then everyone's and then we've got this bid process and something
called like a service disabled, a tribally owned Alaskan status purchase program
so that I can bypass a bid process so that I can I mean, it's like, yeah, the
whole thing itself is like, that's why I really just don't do work with the,
with the fed. I will help people be get Cmmc certified so they can sell to the
fed, But understanding that process is like, is this what we're talking about
though? Is that what you're saying? Is that why we have all this?

Tim McCrosson: Like it is a portion, right? So I was always career fed. Like I
don't look at it as being team red or team blue. It is black. And so it doesn't
matter what party you come from. You can find good things to do from an IT
perspective regardless. But the problem that we needed to solve was in terms of
budget authority. The CIOs at the departments did not have the authority to say,
this is what we're going to buy. That authority was dispersed among the programs
and the bureaus. And so we put policies then in place. the most significant the
federal CIO at the time was Steve Van Roekel. Mhm. And what we did it was called
the CIO Authority's memo. And I remember it distinctly as if it was yesterday.
It's going to very wonky, but it was OMB memo M eleven twenty nine, which was a
watershed moment in federal. It. Because that was the one where we said, if it
is commodity, it. So infrastructure types of things laptops, network, mobile
devices, software. If it's commodity, the CIO of the department has the
authority to manage those things. And that was the first time in twenty eleven
that anybody had ever conveyed that type of authority to a CIO. Does that work.

Phil Howard: Now? Are people savvy enough nowadays to know, though, to know
about APIs and web hooks and interconnected software and stuff like that? could
that screw up different solutions that might be needed across the government?
Well, this is kind of the thing that. So this is if we want to really get deep
into the psychology of how high level CTOs or CIOs make decisions. A large
majority of CTOs, and this is what I've found based on twenty two plus years of
seeing how people make decisions. Well, first of all, it might be a political
decision. It might be someone might make a decision because so and so's son
works at X, at Microsoft versus Zoom or something like this, or Comcast or
numerous other Adobe like. we can buy our Adobe from fifteen thousand different
ways, but we're going to buy it this way because so and so's son works over
there. That's one way that's a political thing. The second thing would be. It's
just safe. It might not be the best decision, but we're going to make this
decision because I know it's like the old saying, it's like no one ever got
fired for choosing IBM. So was it IBM at first? And then yeah, then it was no
one got fired for choosing AT&T. And what does that mean? It means that people
make decisions not based on what's the best possible decision, technology wise
for the company to make decisions based on, what's the safest. And now nowadays
I would say it's almost the opposite. People make decisions based on fear of
missing out. If we're going to talk about like you said, AI and stuff like that,
people are making all kinds of stupid decisions and wasting money. And I don't
know how that's any different from some of these other ones. But I guess what it
is, is it's people don't always choose the best solution. They choose the
solution that they can defend.

Tim McCrosson: I would say, bedrock sort of policies in at least in the federal
space, is a collection of regulations called the Federal Acquisition
Regulations, the FA, and that is intended to govern all of those acquisitions so
that we avoid nepotism, right. So that we avoid favoritism. Right. and so it's
you can't award. And I would have to say that most people there are very, very
specific, notable exceptions to this rule. But most people. Absolutely want to
make the most efficient and the most economical acquisition that because
honestly, I saw it like everybody else is I'm not spending my money. I'm
spending the citizens money when I make an acquisition, when I go and put a
contract out there.

Phil Howard: so it's good to know that the technology guys care about this stuff
because I have some money, get thrown away in all kinds of crazy ways.

Tim McCrosson: Well, yeah, I mean, there's always stories about four thousand
dollars toilet seats and two thousand dollar hammers and those types of things,
right. And those exist for sure.

Phil Howard: It might not be two thousand dollar hammers. but it might be. We
don't know how many hammers we need for the job. So we're going to buy two
hundred thousand in case we run out, because we only have this one bid period
during the year. And I don't want to do this again. So and I'm writing the RFQ
or whatever, this this is just what I've kind of seen. And then you've got, I
don't know, there's a lot of stereotypes that get thrown around DC, like the
retired generals that everyone that are running around with the ponytail and
they've got their heated driveways and you see their multi-million dollar houses
and stuff, I don't know, I stay away from the government. Space is such a crazy,
there's so much red tape and stuff to cut through that. It's kind of like this
double edged sword where you have it's like the policies are in place for
everything that you just said. That is good to make the best decision, the
safest decision to fall within these reasons. But so then naturally people are
going to. How can I get around it? Yeah, like how can I partner up with a again,
service disabled, female owned, tribally owned company so that I can use this a
bid process to get through the processes faster? Yeah. When I saw that, I was
like, man, it just scrambles my brain. Can I just work in technology, please,
and do what I love?

Tim McCrosson: I'm with you on that. And interestingly, I was talking to a
couple of guys who used to sell hardware to the government. And they made the
comment, oh boy, we always look forward to August and September because the end
of the government fiscal year is October first. Right?

Phil Howard: Yeah.

Tim McCrosson: And so historically, agencies and departments would have money
that would expire at the end of the fiscal year and spend it. What is the one
thing use or lose, right? That's the concept. Use or lose, right? You can't
carry over the money. And what is the one acquisition that you can guarantee,
almost guarantee is going to be a safe acquisition at the end of the year that
you're going to be able to spend that money on. And it's almost always laptops,
right? We'll just go and buy laptops.

Phil Howard: Mhm.

Tim McCrosson: And in my experience, I studied opportunity to work at agencies
that were on opposite poles for this extreme. I worked at Housing and Urban
Development, which was always woefully underfunded and never had enough money to
replace the laptops that were aging out. So it would not be odd for us to see
laptops that were in service for seven years or more. So we would run our
laptops until they fell apart. Yeah. And then you would have to beg to get a
replacement and a replacement laptop might not not even be new. Yeah. And I
worked at a different agency that was very, very well funded and that agency
replaced their laptops every eighteen months because they could because if they
didn't spend the money, they would get less money the next year. And so when I
eventually went to the white House, this was one of the things that I absolutely
was focused on cure. Right. Is because my goal from a policy IT policy
perspective was to put agencies on a diet to fix both HUD and this other agency
so that HUD would be forced to replace laptops on a more normal pace, consistent
with everybody else. And this other agency would be prohibited from replacing
laptops early. So I created a policy that said, look, you've got to pick your
refresh cycle and then you've got to stick to it. And most agencies picked a
four year refresh cycle, which meant the policy was that I get to replace twenty
five percent of my laptops every year. And from my perspective, it actually
helped to sort of even out that distribution of, acquisition from one year to
the next. We weren't buying all laptops for the entire department in one August
or.

Phil Howard: There's probably a model for that. That's actually an interesting,
it's probably an AI model for that too. Like what is the most efficient
equipment, like whatever turnover process for staging, because obviously you
have to re-image things or however you're staging them, sending all these things
out. However you're doing your desktop design, all that type of stuff. Well.

Tim McCrosson: Yeah, that's an interesting point because five years later, I
actually went to USDA as the assistant CIO in charge of customer experience. And
so I now had one hundred and seventeen thousand people who got all of their IT
capabilities from me, including laptops. And at the time when I came there, we
were imaging and deploying laptops in a completely fragmented manner. Right. So
each office, USDA has about four thousand four hundred different offices. And so
we had people, I had a team of about thirteen hundred people who worked for me.
And so part of their duties would be every month, some people would have to
image and deploy several laptops. And when I did the math, I figured out that
what I needed was the capacity to image and deploy thirty five thousand laptops
a year. That's about our twenty five percent refresh rate, which is what we
chose. So because I had that policy experience from the white House, I
recognized the issue here and created a new capability called the Enterprise
Depot, where we would have regular shipments from. In that instance, Dell that
would come in to replenish. And our image time was. When I first got there, it
was more than eight hours to actually image a device and Intune and all of the
capabilities. We got that down to less than an hour, and then we can ship out
devices the exact same day, which turned out to be critically important during
the pandemic.

Phil Howard: Yeah. Well, I mean, that's the pandemic. I had so many crazy
stories from it.

Tim McCrosson: I got the craziest story. if you need to consolidate networks.

Phil Howard: Mhm.

Tim McCrosson: The best time to flatten competing networks is when everybody's
working from home. because I was able to consolidate seven networks between
March of twenty twenty and Memorial Day.

Phil Howard: And I do like a plandemic. We should just do a pandemic for it. And
this is just like a test. And then we can consolidate networks.

Tim McCrosson: Five hundred switches came into the loading dock, and it was easy
because nothing else was working right. No one else was there. The only truck
that showed up that day was my truck with from Cisco that had five hundred
switches on it. And then we started. We put together an assembly line and just
deployed those switches to telecom closets over the course of the next two
months. That is amazing.

Phil Howard: Yeah, it's actually kind of like, that's like a fun project. That's
where like, it becomes kind of like, that's like a fun project.

Tim McCrosson: well, I did go a little crazy on that project. I'll admit it.

Phil Howard: I mean, there's so many areas where, it's where you can go find ROI
as you grow and kind of like the enterprise role and you become more of a
leadership. It's like, how do you let go of some of that stuff? And how do you
let other people take on the business of streamlining, and bringing more ROI to
the table, it's like, how do you really start to kind of like let go and trust
your team to do that? Because if you start to think about it almost, you'll just
be like stressed and won't be able to sleep at night knowing all of the endless
to do list of things that there are in it. How do you deal with the stress?
Because for any IT director, there could be easily twenty five projects that
people are asking you to do or twenty five different areas. It's like, how do
you really kind of grasp get a hold of all that and eliminate things and really
kind of wrangle the business together and be on the same plate with the C-suite,
so to speak, on what the main challenges are and what challenges we need to kind
of just say, hey, you know what? Forget about that because it's not going to get
done and it's not important right now or it's not important enough.

Tim McCrosson: Well, you have to invest in both managing up and managing down.
Right? And so when I look at managing down, it is to what degree am I equipping
and cultivating people who can take my job. That's my goal, right? Is to put
myself out of a job because I have built up people who, can exceed my capacity,
my ability. I was really, really happy. Twenty twenty five. I was the mentor for
different people, and all four of those people were promoted that year. Now, one
of them was promoted because he was in the reserves. Right. And he was promoted
to captain in the reserves. But I still count that as a win. So four out of
four. And so anybody who thinks that it's not worth investing in those types of
scenarios, the mentoring people and really investing yourself in that you're
selling yourself short at the same time. You have to cultivate those
relationships with the executives. And so at the same time that I was mentoring
these people, I had a dilemma and I really needed the executives at the time, I
was rural development. rural development in USDA is a big bureau. They make a
lot of loans. And I had a situation in which we had literally forty thousand
vulnerabilities and we were never going to get beyond. There is, I would say,
before I got there, years of deferred maintenance. And it created a degree of
technical debt that we were never going to overcome. And so with my support from
my CSO, I developed a solution to get us around that. And that was to deploy a
sassy. And so if I had a sassy, then I could obscure the forty thousand
vulnerabilities that I was carrying on my network, and I needed three million
dollars from them in order to acquire and deploy that sassy.

Phil Howard: Can I take a guess on who it was?

Tim McCrosson: Sure.

Phil Howard: Cato networks.

Tim McCrosson: Cato is great, but Cato, in fact, they're number one on the
Gartner Magic Quadrant. You were very close. But Cato is not FedRAMP authorized.

Phil Howard: I bet you they are now after losing.

Tim McCrosson: Maybe. I don't know that they are. Zscaler was the only venue
that had a FedRAMP authorization, and I worked with them for more than a year to
get that project going. Ultimately, the thing that sold it for my executives was
I had my CISOs in an executive meeting, literally demonstrated in a live fire
exercise how easily she could take control of the network from an adversarial
perspective. And then I told him, I said, look, we have sixty billion dollars
under management for all the laws, and that money is at risk. So we have no
choice but to go and address this issue. When I did that, the they saw how much
risk we were facing. They brought the money to the table. We started the project
just a few weeks later. So it's managed both up and managed down. You've got to
have both sides, great people above you and supporting you, great people with
you and giving you those brilliant ideas.

Phil Howard: How big of a sale was that?

Tim McCrosson: That was enormous.

Phil Howard: In other words, like how much like how big of an ask was it? And
the reason why I want to ask this because I want people to know what's possible.
Give people hope.

Tim McCrosson: So I was the co-chair of the Information Technology Executive
Review Board. Okay. And even though I was the co-chair and could set the agenda,
that was not enough. What we also had was a separate executive board. it's
called the Enterprise Risk Executive Board. And that was made up of completely
different people. And usually the risks that they're looking at are human
capital risks, risks that the financial systems would have problems and not pay
people appropriately and those types of things. So it was really weird for the
CIO of the agency to basically come to the risk board and say, I have a risk
that I would like the enterprise risk team to consider. But then they did
consider it, and they prioritized it as the brand new number one risk facing the
organization. And so with both the IT investment Board saying this is a very
high priority thing, and then the Enterprise Risk Board saying this is our
number one risk. Then it became something that the administrator absolutely had
to support. And so, yes, it's cultivate that support, work with your peers to
help them understand.

Phil Howard: at the end of the day, like, how does one get approval for
something that's not in the budget? Were you borrowing from the risk guys
budget? Were they like, well, no, we're in on this and we've got money for this,
even though it's not in the IT budget. It's kind of like we're sharing that
together and like, yeah, we're going to make this happen.

Tim McCrosson: Well, federal budgeting is very challenging sometimes because you
really have to be two years ahead in your budget cycle in order to get there. So
sometimes the political appointees have reserved dollars that they can point to
at their disposal. And in this instance, it was some of those reserved dollars
in support of one of the programs that they prioritized.

Phil Howard: We will find a way.

Tim McCrosson: Yes.

Phil Howard: people want to find a way, they're going to find a way. Just for
everyone out there listening, both Z, scaler and Cato are both close partners
with us, so if anyone would like the extra special platinum support through
Zscaler and Cato, then you can contact the back end program at
info@youvebeenheard.com and we will make a red carpet introduction right over to
the best team over there that gives us extra support in VP level access and
Premier pricing.

Tim McCrosson: Cato is supremely impressive. just a couple of months ago, I
actually had the CEO of Cato at an event that they hosted down in Fort
Lauderdale. And man, talk about really being ahead of the curve, both in terms
of implementation, timeline and usability. Yeah, I will tell you, it was a one
hundred percent part of my three year roadmap to implement the keto sassy
capability. We weren't going to get there in year one or two, but year three So
that was what my target was.

Phil Howard: From secure cloud access to mobile devices, accessing the network
to there. They're not even known as an SD-Wan provider, but they have that
feature backhauling traffic. when we were in meetings before, I've had it.
Directors say, if you take Cato away from us, I will quit tomorrow.

Tim McCrosson: It's the ease of implementation is the key. That's probably what
sets them apart. And don't misunderstand, Zscaler was great and I thought the
Zscaler solution was implemented very well too. It was quite frankly as turnkey
as I thought it could be. And then Catos is even more so.

Phil Howard: It looks like they started their FedRAMP process in actually March
of this year. So yeah, still not a FedRAMP, but I don't want to sell into the
fed anyway. So if anyone out there that needs Cato, you know what I mean? It's
like I don't want to be in the fed anyways. I want to help the people that are
in manufacturing, health care and all those other spaces. But for all of you fed
guys out there that are working within the government, they have started that
process and it looks like in March. So according to the news here. so all right,
what's your prediction? Where do you see us? eighteen months from now, it
doesn't have to be an AI prediction or something like that. But how do you see
the IT leadership space changing? I think we're going to kind of level out of
this bubble and realize that people wasted a lot of money trying to implement AI
and a lot of time and starting to see that it's really more about implementing
various different point solutions across AI that really make people's jobs
easier. There's no doubt that it's that it's helping. But I do believe that
there is a level where you can go too far and it can become a kind of maybe a
project nightmare or sinking debt and waste of time.

Tim McCrosson: So I have a couple of thoughts on this. The first is I've been
working with a company that created, I'm going to say thousands of microservices
and then coordinated and wrangled them together to. We were talking about the
federal acquisition regulations earlier. Right. It's a very complex process
that's intended to ensure fair competition for federal acquisitions. Right? But
it has a lot of stops on that process. And I've started working with a company
that has used AI to absolutely short circuit this very complex process. And so
you can go to their product and basically say, here's my requirements. Can you
write a statement of work? here's some information about the magnitude of what
we want to do. Can you develop a cost estimate? Can you identify the terms and
conditions that we should put into a solicitation. And then you receive
proposals from industry right. Based on your request for proposal. And it's
going to have both technical and a cost proposal. And then you can pour that in
and say, can you evaluate these technical proposals to tell me where their
deviations from my work statement are, and can you evaluate the cost proposals
to help me understand to the degree and since I've been in many acquisitions, a
lot of times industry will say, you're comparing carburetors and bananas and
chipmunks, right? Yep. Because if it's impossible to conduct a good comparison
among the offers, then it's sort of a crapshoot. It's in the industry's favor to
do that. To the degree that the government can get an apples to apples
comparison is always going to be better for the taxpayer and government. And so
by throwing it through the AI, you can actually get closer to that apples to
apples comparison And tell them the industry that, hey, can you consider
revising your proposal to be this many people? And what is your range of rates
for this? Because that's not consistent with what we're thinking. And so in a
negotiated acquisition, you can actually get much closer to an apples to apples
comparison than you ever could before. So that's one. And I think that AI has a
lot of promise at the macro level, taking these very complex processes and
making them maybe not easier, but more manageable and doable.

Phil Howard: It definitely takes down the old man hour effect of data entry. And
I mean, I just remember as early as three years ago, when you have to back to
your five hundred replacing during Covid switch scenario. Yeah, right. Like I
can remember doing network refreshes on old Mpls VPN backbones where we were
replacing T1's and we were forklifting networks. And when you do that on a one
hundred location manufacturing or logistics company or something like that
across North America and Mexico and Canada, and then you've got manufacturing in
China and stuff like this. When you start to actually do that, back in the day,
it was a very manual process. It was email China Telecom and get pricing here
and talk with an engineer to find out this and then price this and price call
Kato so you can get around the Chinese firewall. Right. And you're manually
putting all this stuff into spreadsheets and having assistants do this and that
type of thing. That's on a very simplistic level, right? That type of thing. And
then looking at fiber location maps and what's the fastest routes, and how do
you know that this provider is not just quoting another of the same provider? So
you've got depth diversity. There's all kinds of things, right? That type of
thing can take hours now. And for the I.t director, back in the day, it took
eight months for the guy, for his partners that were helping him. It would take
a couple weeks with a team of twenty five people, all different vendors working
together and quoting things. Now that can literally be done in like hours.

Tim McCrosson: Mhm.

Phil Howard: If that's.

Tim McCrosson: Revolutionary.

Phil Howard: Now is if it's accurate, that's another thing you have to have like
be able to go through and verify accuracy, but it's easier to go through and, do
that and find the missing pieces and stuff and verify stuff and find little
hallucinations here and there than it is to that a human would have done
anyways. A human's going to make mistakes and keystrokes and move decimal points
and stupid stuff like that, which just reminded me of inorganic chemistry in
college and the tests that I swear I got an A on, but somehow I had put a
decimal place in the decimal point in the wrong place. And then I got a D. And
that's the thing, right. That's clearly where it's going to, very, very helpful.
I guess the other thing would be is, how well do you think my assumption is it's
dumber than I thought, but how well do you think people really know the general
user? How aware is the general user of AI and how to use it, and how to use
various different LMS and tools?

Tim McCrosson: I think there's a rapid acceleration in the knowledge that the
general user has, and I think that that's going to be a fun like it's no
different than the dot com knowledge continuum. Right? And so people didn't know
how to use websites and e-commerce. And then all of a sudden they started,
right. And so you had these early adopters who got on, and then eventually they
coached the normal regular people, regular Joes, and then everybody's buying
stuff from Amazon. And so then it's just the laggards who are I gotta go into
the store and buy the thing, right? But that's now a much smaller portion of the
population compared to the people who are buying online.

Phil Howard: Are you still an idea? We should have AI searching Amazon for like
crazy deals and then reselling them in another somewhere else or something.

Tim McCrosson: but I have another take on this as well that I think AI is going
to change the way or change our conventional wisdom on a very specific topic. So
the topic that I would put out there is we have these, notion that commercial,
off the shelf shrink wrap stuff is always going to be the cheapest, best value,
right? And remember, I'm in government acquisitions, right? And so when we think
about software, especially sort of big ticket ERP software, right, SAP, those
types of things, big, software packages. The conventional wisdom has always been
off the shelf. Get it off the shelf. go and implement a vanilla solution for
your general ledger, accounts payable, accounts receivable, all that stuff.
Right. Do not customize. And the reason that you don't customize any of that is
because it makes your upgrades over time cheaper, more efficient, easier to
implement upgrades. I think the AI is on the cusp of flipping that conventional
wisdom on its side because that make or buy decision that says go and get a
solution. Now, compared to the cost of using an AI and vibe coding, a very
customized solution to my environment that meets all of my requirements and
doesn't give me the just stuff that I never needed anyway. I think that that
when you look at the cost now AI is driving the cost of that custom development
solution lower. Is it low enough that it's in terms of total cost of ownership
or life cycle cost? Cheaper in the long run than the cost solution? I don't
know, given some of the licensing costs, maybe.

Phil Howard: So I'm I'm thinking about how we've struggled with this ourselves.
And I put all that it means is that I live with the same pain that everyone else
lives with, at least from an IT directors and implementation standpoint,
especially when you say CRM, ERP, and these various different things. And I
can't imagine like a massive ERP forklift would be just so difficult. And so,

Tim McCrosson: I was listening to your podcasts a couple a few weeks ago, you
were talking about CRM and Salesforce, right? Yeah. So the question here was,
should I go and make that Salesforce investment versus go and create my CRM
capability using AI capabilities and build it that way. And so this then is the
sixty four thousand dollars question of It, which is like a hybrid.

Phil Howard: Yeah, I think it's going to be someone that has the team, the money
and the manpower to build the initial build with the hybrid CRM in it. So for
example, we've been like wringing our hands over what CRM do we use for like
ever? And it was, do we just stay with go high level because we've had it
forever and we've been getting it free from another agent who's like a partner
with us. And we do trades with like that type of thing, right? We're like, well,
case feels kind of like the go high level, which is the other one was the white
label. So go high level has like everything that you've ever want in like a,
it's basically like they, they have a team of developers like, okay, just build
it all. We're going to just throw it all in one thing and it's Legos. It's just.
but then what happens is the interface becomes kind of like an administrative
nightmare for some people that don't really know, kind of go high level. If you
don't like the GUI, you don't like the GUI. It's just like, oh, I really want to
love you because you have absolutely everything. Like literally everything.
Yeah. Texting webinars, like, I mean, integration with Zoom every a p I and then
like you've just got everything that you could, you know, you want. Oh, yes, you
can do that. Yes, you can do it. But the GUI just becomes so GUI, it's like, do
you want the iPhone or do you want like the BlackBerry with the flip out
thousand buttons? It's just like, I want the iPhone, but I would have to go do
all these other things. So I was like, okay, so then I guess we could build
Salesforce and we could have this API and that blah, blah, blah, blah. Well,
there's a CRM out there called, I think it's twenty CRM. I think it's called
twenty. Everyone Google this, it's just free advertising for these guys. Twenty
CRM. I think they're making insane growth right now. Yeah. Twenty twenty dot com
pretty good domain there. I don't know how I got that one twenty dot com.

Tim McCrosson: Yeah.

Phil Howard: Build your enterprise CRM at AI speed. So they give you like that
out of the box, vanilla CRM like right out of the box and it's gonna like pull
in contacts and emails and give you a lot of stuff out of the box. And then
they've just got a really nice AI interface that will build all of the bolt ons.
And it's really, really customizable. And I think you could probably pay a
developer or somebody or someone else's good with AI and a developer to kind of
like build out your enterprise CRM pretty darn quickly. Customized the way that
you want it, like the way that you want it, the way that your end users want to
use it, not the way that we have to kind of change Salesforce to make it work
with, you know I mean, we kind of have to have these dispositions this way and
the drop downs this way, like no. So we kind of went down that route and we were
like, oh, we had to kind of invest our time. And then we have to be very careful
because we're podcast startup and we have to just kind of be very careful with
how we invest our time. And that could be like another really deep question,
right? Like, is this the biggest challenge right now? The CRM, is that really
the biggest challenge right now? Like how I put Tim's name into the database and
make sure that, you know, he knows that we're doing a round table this month.
Like, is that the biggest challenge? Probably not. So that's kind of why we.
Right. But it's like the shiny objects. Hey, look what we could build. Look what
we could do. And then we could do this and we could do that. We could do this.
And that's the kind of like there's this constant mental battle, like the CTO
and the CEO at the same time. So I can create my own problems. So as I think one
of the keys to being a really good IT leader you tell me is how well do we know
business and how well can we keep our own people that are asking us to do all
kinds of crazy crap and projects all the time on track, and what's actually the
actual vision and mission of the business? Because it guys as much as they say
we're the Department of No or whatever, we're actually kind of the Department of
yes. Like, yeah, I could do that. Yeah, that'd be cool. Yeah, I could do that. I
actually don't think we're the Department of no, I think we should be like the
Department of Hell no all the time, you know what I mean? And we should be the
department of. I'm trying to remember who said it was like yes, but no. Or was
like, yes. But first, is this a major challenge of the business? How does this
apply to the main challenges of the business right now? What's the ROI going to
be on this? It's kind of like the the AI roadmap, right? Like, do you know what
AI is? First of all, do you have a steering committee? Do you know what AI is?
Who's on the steering committee? Probably should be the most important people in
the company or some of the most, you know, department heads. Two. What do we
actually want to solve with this? Like, what are our major problems? are these
actual problems? Okay, can I solve that? Maybe is the data in alignment and
cleaned up? Step three for that. Step four guardrails and security. Is this
going to leak all kinds of crazy data. Or is this going to screw us up and
everything like that. And number five, is it worth doing? Is there an ROI to it?
Or should we just hire another person for data entry or something?

Tim McCrosson: I mean, what you're hitting on is the business case aspect for
these types of projects. And everybody has sort of a high fever and there's a
rush to go and, not be seen as being behind in terms of AI development and
capabilities. But I think the IT leaders Responsibility is to paint a picture
and show everybody what the North Star is. This is where we're going, and we're
only going to do the things that get us to this direction, because we could go
left and right and down, but we're going up.

Phil Howard: In conjunction with the C-suite. Like we are a team one hundred
percent.

Tim McCrosson: The IT strategy is born from the overall organization's strategy.
You tell us what you want to achieve as an organization, and we will develop an
IT strategy or IT roadmap to deliver that.

Phil Howard: You know what's actually bothering me, which actually I'm starting
to rate people on nowadays, is I've looked at some pretty big vendors as of
recent. So I'm talking like For me as a small business, investing one hundred
thousand dollars. And that's a lot of money for a small business, right? So I'm
looking at only the best. What's really interesting to me is I'm evaluating the
best based on, are they going to tell me they've got this great AI product? And
that actually makes me nervous because I've gone through the motions of vibe
coding things, of using AI in the business. We have our entire AI driven process
for producing the podcast, but the most important thing is that the human aspect
stays intact so that we're actually using the real words of humans. And that's
the beauty of it's kind of this weird. because it's a language model, right? But
that's the beauty of how we don't use a language model by using the actual
language. It's really this weird deep psychological thing. So it's like it's the
language learning model is based on language learning. For anyone that really
knows the deep understanding of the algorithms of how an LLM works and
everything. It's pretty wild. Only to come full circle and say, I want to use
what Tim says exactly. Not what the LLM comes up with or its ideas of how Tim
feels, because people can. They're starting to very quickly realize, oh, it's
another AI written email. Like, I'm so sick of this slop. As nice and flashy as
it sounds, I'm sick of hearing unlock. I'm sick of hearing everything. It's the
great unlock. Like, why are you saying unlock? Like everyone's saying unlock
nowadays. And I'm like, dude, what's going on? So I'm looking and evaluating
this really, really high level vendors. And I'm kind of evaluating them on like,
are you not using AI? Because that might actually make me feel comfortable that
there's still a human in charge, but everyone has to at the same time say, we've
got this great proprietary AI thing that does this. And it's like, this weird
double insecurity thing. Do you understand what I'm saying? Do you get that
feeling a little bit?

Tim McCrosson: For me, I think the key is technology is technology. Let's make
sure that we keep technology in that lane. But it's the relationship with the
people who run the technology, right? Are you whatever company it is, whatever
organization it is, big or small, do you believe that they are going to help you
and are you building that long term our relationship, right? We were talking
about Salesforce earlier. And I'll tell you, I have a significant affinity for
people at Salesforce because quite frankly, yes, there's a lot of AI behind the
scenes and there's a big army of people, very qualified people. the people that
I dealt with on a day to day basis? Yeah, we're one million percent invested in
what we were achieving together as a team. And so, for me, that counts more than
probably anything, right? Is how invested are they in understanding my business
and then bringing the right solutions that solve my problems today? I think is
more important than anything. It's the relationship.

Phil Howard: Yeah. For sure.

Tim McCrosson: Yeah.

Phil Howard: So we can't let AI take over the relationship. That's the one thing
we can't we can let it systematize or streamline and make things better. But my
prediction would be, which is probably different than it was again, six months
ago, is that people are going to get tired of, certain aspects of AI really
quickly. I wouldn't want to have it take over customer service entirely.

Tim McCrosson: No.

Phil Howard: Aiding customer service. Yes.

Tim McCrosson: So I mean, we talked about business cases earlier, right? Mhm. So
I had what I called a significant AI business case when I was at rural
development. So a lot of people don't know this rural development. They actually
issue single family housing, direct loans. There's like one hundred and seventy,
thousand people out there in America that when they write their mortgage payment
every month, they're actually paying USDA. And so we're servicing all of those
loans. And occasionally those people won't need to call in and talk to somebody.
And so my AI use case was, I want if Joe from rural America is calling in, I
want my AI to be able to look as that number is calling in to know before the
agent picks up the phone and says, hello? What is going on with that person's
account? Have they missed a payment? Are they late? Do they have a payment due?
Has there been a disaster event that has affected their geography? And so we are
equipping that customer support agent with the right information before the
phone call even starts. So the metric that I was focused on was decreasing
handle time for that agent. I want that agent to be able to address the person's
need as quickly as possible, and get that person off the phone so that they are
happy because nobody wants to call in. You don't want to do it. You're forced to
do it because you have a transaction or a business need that can't be otherwise
addressed. So therefore, this is the last resort you're calling in, and you want
to be off of that communication as quickly and efficiently as possible.

Phil Howard: Being a contact center expert in telecom guy. That's actually one
of the best places that AI assists very, very well is in contact center. Even
from an automated agent standpoint, that's where it's kind of like helpful, like
appointment reminders and things like that. Even outbound calls, like I'd be
totally fine with understanding like a really well voiced AI agent calling me
and letting me know, hey, Phil, I just want to let you know your appointments
tomorrow. Are you still on for that? Could you just press one or two or
something or just speak to me? Just speak to me, you know what I mean? And is
there any problems with that? And then send them to a live agent if they need to
or like you said, calling in and being able to pop a screen, feed an agent as
being an AI agent assist to the live agent of Sally's here, like you said, there
was a hurricane or blah, blah, blah, and she missed her last payment and pull up
all pull up the account and all the screens and feed some stuff along with
sentiment analysis and speaking. Feel you're speaking too fast and too loud. And
it's like I always get the feel you're speaking too fast on my sentiment
analysis.

Tim McCrosson: I mean, the only thing I want, I'm okay with the human being out
of the loop on is I'm sure as a service desk person, Monday morning, password
resets. Just go ahead. We're going to get a ten or twenty X influx of calls on
Monday morning. Yeah, yeah. Just they're almost all of them are password resets.
Just let the AI reset people's passwords.

Phil Howard: There's like the meme that I shared the other day on, like the
calling someone and helping them set up their two factor authentication or
something like that. I mean, in reality, why not? And this is something we did
on a round table and I'm spending extra time because this is just fun. But we
did a round table event on creating your company's cyber security villain and
your company cyber security villains. Really more like a mascot that people
learn to love. But he's the cyber security villains. Whole purpose is to like,
phish you and cause other problems inside the company and create all these
issues. We could create a cyber AI mascot and you could have like an AI mascot
that people actually bond with. That'd be interesting. It's an idea.

Tim McCrosson: I worked at Cisa for a couple of years in cyber security. And
what you're talking about are personas, right? And so yes, there are personas as
a state actor, is it a crime syndicate or crime organization? Is it single
person with an axe to grind? And so those personas has different motivations and
different capabilities at their disposal.

Phil Howard: Yeah. All right. Last question. Yep. If you could go back and tell
yourself one thing, you're going back in time and tell yourself one thing on day
one of your IT career, knowing what you know now, what would it be?

Tim McCrosson: Oh man, there's a big fork in the road that everybody in it will
likely encounter at some point in their career. And that fork is, are you going
to make a choice to stay on the technical path, or are you going to turn and go
down the management path? For me, I clearly chose the management path and I
loved it, right? Because I got to be ahead. There's a part of me that is
remorseful; I mean, nobody's coding in ColdFusion anymore, but that I'm not more
on the coding end of that spectrum. And actually being a developer, I kind of
miss those development days and the creativity that comes from that. The
excitement of, I mean, ultimately is you look back on what you've accomplished
in a day and you can say you can measure it. We didn't have this capability when
the day started, and now we do. and that's amazing, right? But whereas when
you're on the management side, it's a completely different metric in terms of
how you measure success and progress.

Phil Howard: It's definitely more emotional roller coaster. There's more of your
soul out on the counter. There's probably more sleepless nights. And I think
from that standpoint, to applaud you. You took the more difficult path, whether
you knew it or not, because there's days where you're just like, I'm a bad
human. I need to do better. There's just days where there's just it's like very
difficult days. Whereas I know that there's plenty of times where I've sat on
boards or I've been part of an administrative committee or something like that,
and I've just said, hey guys, here's the thing. I'm much better at taking
orders. I don't want to deal with, especially when you're in a nonprofit or
something like that, or you're volunteering in the community. Sometimes you see
things you just don't want to see. You don't want to deal with. Like it can be
very, very difficult. You don't want to know everybody's personal life. You know
what I mean? You just take more emotionally on your shoulders. And I think
again, to applaud you that you have to agree to do that and sign up for that.
And you have to really care and really want to from the emotional standpoint,
from the emotional intelligence standpoint, whereas it's easier to be the
arrogant coder and sit in there and be like, I can always do his job better. Let
me go back and like, talk about how like, you know what I mean? that's how I see
it. Did I hit it correctly? Like some days I just wish I was back sitting in the
bullpen closing tickets and I don't know, doing whatever, fixing things and
playing with the machines.

Tim McCrosson: there's a part of me that wishes that I could just be on a red
team, right? I mean, red team, certified ethical hacker people. They have I
think they have the best job. Right?

Phil Howard: It's the dream kind of.

Tim McCrosson: I mean, you had almost no responsibility. Your job is to find
errors in stuff that everybody else is created, and you get to be as creative as
you can possibly be to gain unauthorized access into stuff with the intent of
creating a safer organization. And the fork that leads that direction is awfully
interesting, too. And so I missed that.

Phil Howard: At the end of the day, everything is kind of a if the grass is
always greener on the other side, right? Even if you were there like that
company could be sold or something like that. But I guess the, question then
could be is, like you said, there's like two, like a fork in the road. Like
there's a third option. There's a third option, which I always ask people like,
what's the end game for it? So the third option would be start your own company.
Or the third option would be create your own thing, right? But then that comes
with a whole other host of problems. Believe me, trust me, it does. It comes
with a whole nother thing, like sleepless nights. It's like the cook that's
always loved cooking his entire life or she's always loved cooking and baking or
whatever it is her entire life. Right? So I'm going to start a restaurant. Bad
idea. You're gonna quickly hate cooking. You're gonna quickly hate all that
stuff unless you're really driven and have like a real mission and purpose
behind that. because then you're going to be managing employees and ordering
paper products and timing. And then there's orders, and then there's
fulfillment, and there's all these other things that have nothing to do with
your passion of cooking. So yeah, if there's anyone out there working in the
government space, whatever, it's the hunt for Red October, whatever it is that
wants to hire Tim to just sit in a dark room and like, break into places, you
could just join the dark side, too. And we've seen that a lot of security guys
kind of like be underappreciated. When I saw in the news the other week that
there was like this conspiracy inside another company that led to a ransomware
attack, and the CISO was collecting on ransomware. It didn't surprise me. Wow.
It's wrong. It's absolutely one hundred percent wrong. And that person should go
to jail.

Tim McCrosson: I knew some of those guys on the threat hunting team over at
Cisa. And you know what? They hats off to them. They do great work. Right. And
so we need everybody. It's all hands. Everybody's got a role to play in making
this whole thing work. Yeah.

Phil Howard: Sometimes I dream of going back and starting over again something.
And then I'm like, I'm gonna be fifty this month. I just need someone to remind
me that I'm probably really close to to death. And then I'll just spread the
word. Everyone, you've been heard. Let's go. what it's about, is the other side
of it leadership and really making sure that it that has a seat at the executive
roundtable is heard and that your story is penetrating the room in the company
when you're not there. So what does everyone think when Tim's not at the table?
What does everyone think when Tim's not there? Are they like worried that we
need to bring Tim for this, right. Versus that sales rep has a really great
idea. I think we should buy that, CRM and yeah, yeah, no, Tim and his team,
they'll implement it. Yeah. Let's go. You know what I mean? Like, there's so
many things that were missed, right? so that's, the mission. So thank you so
much for being on the podcast and coming in and sharing your, years of
knowledge. Any final words or thoughts?

Tim McCrosson: Phil, thanks so much. Man, this was a great conversation and I
really enjoy all the good work you and your team do and getting these stories
out, because I'd spend days listening and driving on in my car listening, and
there's something to learn from everybody and a little bit of inspiration in
every story as well.

Phil Howard: Yeah. And if anyone out there has any suggestions for things that
you'd rather hear, maybe we should break up the show and have some different
sections or something like that. Like, I don't know, AI flops of the day or
something crazy that my CEO brought to my desk today, which we probably cannot
air. Maybe we'll do those as the like. We'll have like a paid only version of
the podcast that only CTOs get to hear or some other people have suggestions to
have, hey, let's have CEOs on and let's ask them when it comes to it. What's
your single biggest frustration, problem or concern? So we can hear from their
point of view too, because it's really not about us versus them. It's about
technology as a business force multiplier winning the day. So Tim McCrosson,
You've Been Heard.

Tim McCrosson: Thank you sir.