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421- There Is No Zero-Fail Environment w/Drew Ludwick

Phil Howard & Drew Ludwick

421- There Is No Zero-Fail Environment w/Drew Ludwick

THE IT LEADERSHIP PODCAST
EPISODE 421

421- There Is No Zero-Fail Environment w/Drew Ludwick

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Drew Ludwick

ON THIS EPISODE

Drew Ludwick did not plan to become an IT leader. He started as a network engineer who liked hard environments, messy infrastructure, and the pressure of making systems work when the stakes were real.

That background shaped his view of so-called zero-fail environments. Drew argues that technology breaks at the worst possible time. The real discipline is building redundancy, preventive maintenance, planning process, and team readiness around the mission that cannot stop.

In this conversation, Drew connects lessons from military communications and the White House Communications Agency to business IT leadership today. He explains why leadership intensity has to change by context, why IT needs a seat in business planning before systems are bought, and why data governance now sits at the center of AI risk.

The conversation closes on a warning most teams will recognize: vendor management is becoming one of the next big security problems, especially as vendors add AI features inside business systems with limited visibility.

Show Notes

Episode Show Notes

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

[00:00:00] Phil introduces Drew Ludwick and his current IT leadership role.

[00:00:29] Drew explains the accidental CIO path from network engineering to IT leadership.

[00:01:29] Why some of the best leaders fall into leadership through the work.

[00:02:02] Drew describes learning leadership by helping team members find the right fit.

[00:05:42] A project manager moves back toward technical work and later becomes a COO.

[00:08:20] Drew challenges the idea of a literal zero-fail environment.

[00:09:25] The White House Communications Agency story and the pressure of dropped secure calls.

[00:18:17] How military stress changed Drew's perspective on IT pressure.

[00:20:07] A special operations deployment and restoring communications under command pressure.

[00:27:07] Leadership as a rheostat dial, from coaching to direct execution.

[00:30:36] Why most businesses are now data businesses.

[00:33:34] Military planning, communications annexes, and business process lessons.

[00:34:29] The risk of IT learning about new systems only when vendors arrive to turn them on.

[00:38:17] Career advice for technical people who want leadership paths.

[00:45:56] Cyber risk, ransomware, AI speed, and the data protection question.

[00:47:18] Shadow AI and why safe use has to be taught.

[00:49:39] Personnel, financial, proprietary, and engineering data as AI-era risk categories.

[00:51:27] How to frame DLP, RBAC, and data structure as business risk.

[00:53:27] Vendor management as the next security problem to tackle first.

[00:56:10] Drew's closing saying: get comfortable being uncomfortable.

KEY TAKEAWAYS

Plan for mission survival, not perfect uptime.
Frame technical risk in business language.
Govern data before scaling AI.
421- There Is No Zero-Fail Environment w/Drew Ludwick

TRANSCRIPT

# EP421 Drew Ludwick Transcript

**Phil Howard:** All right, welcome, everyone back. We've got Drew Ludwig, cio, IT Leader with a very, very exciting pass. Why don't you introduce yourself? IT Director, Operations. I mean, a really nice history. Wendell company has given me just the background of where you're at right now and kind of what's going on.

**Drew Ludwick:** Yeah. Thanks for having me on. I love the show. Super excited to be here. So, yeah, today I'm the IT Director for Architecture Engineering company based in Buffalo, New York. Really more of a CIO role. It's a great opportunity to kind of leverage some of that experience. Some of it's fun, some of it. Some of it not so fun that you kind of referenced. But it's a lot of fun being able to kind of own the whole IT practice. Right. And be more strategic. Right. So if we talk about my background, I come from a very technical background. You could call myself the Accidental cio. Right. I never envisioned I'd be sitting in the big chair one day. I was much more of a network engineer, keyboard warrior. My passion was crawling through networks, building and maintaining networks. The tougher the environment, the better. And I just. I love doing that, and I guess kind of my path kind of brought me here today. So, yeah, I think from a leadership

**Phil Howard:** standpoint that the best leaders, at least the best leaders that I've always run into, ended up in leadership. Not because they were actually aiming for it. They kind of just became that or fell into it. Anyone that's usually asking for leadership is usually, not necessarily always the person that we may want in that position. So not envisioning that you would be there someday, what is it that you think ended up landing you there?

**Drew Ludwick:** Yeah, no, that's a really good point. If that's all you're trying to do, maybe this isn't the place for you. Right. It is a tough business. We do this because we're passionate about it. We love what we're doing. Usually there's a technical aspect or component of IT that draws everyone in. And that was definitely the case for me. Network engineering. I think I started when I started becoming a leader. And in my mind, it's a very clear kind of transition. Was when I got out of the military and started working in private industry and started having team members working for me, being responsible for technicians in the field, for project managers. Really where I think I fell in love with the leadership side of it was in. Was in taking on team members who were not necessarily thriving somewhere else and being able to work with them and help them find their passion, find that One area or that one piece that they love doing that they want to do, and then when you see that turnaround, that's pretty satisfying. And I just kind of stumbled upon that and discovered I was decent at it and just kind of kept building from there.

**Phil Howard:** We have on the agenda today to talk about zero fail environments, which is very exciting. But before we get into that, what you just mentioned is actually a very difficult thing to do, which is to take someone that may not have been successful in a certain role, help them find their passion, or help them be successful. What do you mean? Like, can you give me an example? Can you. Is there. Is it a matter of passion? Is it someone just being connected with what they like doing or finding meaning in their life and work and not feeling like it's a grind or like, how are you putting the. Are you putting those pieces together and helping someone find success where they may not have been successful before?

**Drew Ludwick:** Yeah, I mean, I think we've all seen people that are doing their jobs because it's their job, right? They get into the field because they think they like it. One thing leads to another, and they've been doing it for a few years, but perhaps they aren't really enjoying it. Right. And this is, again, it is tough enough that if you don't love it or you're not passionate about it, it can wear you down. So in my experience, early on, I was lucky enough to have a challenge thrown at me. Hey, this individual over in the survey team isn't thriving, right? They're kind of on their last leg right there.

**Phil Howard:** What does that mean by isn't thriving? Is that like, I go to a Reddit forum and I find the rant page where they're just like, my, this sucks, I'm done. Or is it the type of person that just walks in and throws a bunch of paper in the air and is like, have a nice day, guys, I'm out.

**Drew Ludwick:** I think it means they're about to get fired, right? That's a nice way of saying they're on their last breath. And the ask was, hey, maybe you can do something with this individual. So you talk to people, right? As a leader, you got to know your team. You got to understand what drives them, what their passion is, what they do when they're not at work. You can't always be happy at work. We're all going to have good days and bad days, and sometimes you got to do jobs you don't love doing. But if you're lucky enough to find that passion, right? And at the time, my team was pretty diverse. We were doing utility work. We were doing in building work. We were doing mixed networks, fixed wireless. We had a bunch of different disciplines kind of within the team so we could move people around and let them try different things until they find that passion. So some people just need somebody that's gonna care for them to show that you're invested in them as well. So. And those things help. And that's kind of how I got there, I guess.

**Phil Howard:** Okay, so did we turn said person around or did said person get sent around? Sexy. Yeah.

**Drew Ludwick:** Yeah. No, but I've done. I've been lucky enough to do it a few times. In most cases, successful. Right. Like, one example is I had a project manager that I took over on the team and was really just kind of punching the clock. Right. Coming to work, doing. It wasn't all that great a project manager and wasn't willing to kind of do the things, needed to get really good at it because they weren't passionate about it. They were just getting by. But as you talk to them and get to know people, I learned that this individual was passionate about engineering and got him back into the more technical side. And he ended up being a COO for a wireless Internet provider and doing a lot of good things for a lot of years there.

**Phil Howard:** And the reason why I ask a lot of this stuff is I've had. I think it was Alex from Mosey put it right. He's like, if the first person you think about in the morning is when you wake up in the morning is the first thing you do is you think about this person, you feel like a significant amount of stress or frustration. Then he's like, it's time to just end that.

**Drew Ludwick:** It's.

**Phil Howard:** It's time to just cut. It's kind of just kind of like, cut the lifeline at that point, because you're not doing them any favors, and they're not doing any favors, and it's really just wasting the company time. So it's just kind of what made me think of that. And I. I've been the type of person that would maybe wait a year too long sometimes to make the decision that someone needs to go just because of whatever you care about the person you want to put the time and energy in. You want to seem to be successful. But in reality, it's like you're. You're not doing. You're not doing them any favors or definitely not helping the company out anyway.

**Drew Ludwick:** Yeah, unfortunately, I've had a few of those too, where you got to make that decision and do what's best for not only the company but maybe for them. Right. And I think if I were to try to label what the difference is between somebody that you want to invest more time in and somebody that you need to make that tough decision on, it's that attitude. Are they willing, do they do they want to grow and change or they just miserable and just and and don't want to, don't want to work themselves out of that. So sometimes you do have to make those tough decision.

**Phil Howard:** If your Internet goes down and you're calling carriers yourself, that's not strategic. It we help team centralize monitoring proactive tickets and escalation across every location without capex. Less noise, more uptime, make it boring again. Just go to you've been heard.com and answer the seven questions to simplify, streamline and save. Let's talk about the fun stuff. What does a zero fail environment actually demand of a person psychologically? What does it mean? What is a Z? We're supposed to be talking about a zero fail environment. What is that?

**Drew Ludwick:** We talk. I mean you probably hear the term a lot. Everybody, everybody thinks they're working in a zero fail environment. I would argue there isn't really such a thing. Right. Like if like we've both been doing this long enough to know technology is going to break at the most inopportune time. You can build redundancy into it and you can have process in place to work around those failures. But at some point you're going to have to overcome some sort of failure. So in that sense, I guess a zero fail environment is one where the true mission requirements are such that you do have to have enough redundancies in place and you have to do enough preventive maintenance and you have to be proactive enough that you're replacing stuff before it breaks and you're just spending a lot more. Right. It's a lot more expensive way to operate. In the end you just have this

**Phil Howard:** might do it more of like a mindset thing because mine's like in an only fail environment. Only fail forward environment. I want to hear this story about connecting a president with rusty copper lines in Buenos Aires to another world leader.

**Drew Ludwick:** Yeah, I don't know if it was actually Buenos Aires, I'm trying to remember. But when I was in the military working for the White House Communications Agency, we were going through a transition. At the time it was most of the world had already moved on to digital over analog. But the secure communications environment at the time really relied on Analog still to encrypt voice. Right. So if we're encrypting voice at a very high level, we were doing it over copper lines and analog encryption at the time. And the transition was going on because the President had been somewhere in South America and calling back to the United States where he was probably patched through to somewhere in Europe. Right. Like there's this incredible collection of cross connects that has to happen. That call had failed once or twice. Right. And when the President is talking to other world leaders about world leader issues, there's very little tolerance for dropped calls, encryption dropping out. So that had happened. And the agency I worked for was they weren't bad at what they did. They did test calls prior to the actual call. They would have tested a few times, they would have had the call up for a while, secure. It would have been well rehearsed and well practiced. But sometimes those types of things happen anyway with technology. So the call failed and stuff rolls downhill. And we, despite the fact that the infrastructure, we didn't own it. From Buenos Aires to D.C. and from D.C. to somewhere in Europe, there was a lot of commercial civilian infrastructure in the middle of that that was completely outside of anyone's control. We were kind of forced to move into a digital solution now. And as we transition to digital, there's just one zero fail environment to another. And do you technically overcome those challenges? They're just different challenges. Right. You're still transiting infrastructure you don't own. And whether it's over IP or if it's over analog lines, it's still stuff you don't own. So again, you go back to having redundancies in place, having a backup call. You gotta have process in place to overcome something like that.

**Phil Howard:** Was it the encryption piece or was it just hitting the PSTN and hitting various different switching. Was it like the long distance network?

**Drew Ludwick:** It was the long distance network for sure. Yeah. The encryption was very fault intolerant. And if you just got one bad connection somewhere in that PSTN maze, that was all it took.

**Phil Howard:** I kind of missed the old days of copper lines. They're still there. If you make a call from somewhere to somewhere, most likely it may still be hitting some piece of copper. There's still people replacing POTS lines by the day. And Mitel phone systems, for all of you out there that still have my. For all of you that are still sitting on a mitel slash Shoretel phone system, maybe Avaya. I still go to the hospital and I still see Nortel phones with Nortel branded Phones sitting on the wall. So they're still out there.

**Drew Ludwick:** Well, and it's just a lot more expensive now. It's not regulated right. And yeah, elevators, right, they rely on copper somewhere. You're going to cross that path with that for sure.

**Phil Howard:** I don't know if this is the correct assumption or not, but I find that a lot of the people that we've interviewed over the years are ex military. And my very first military interview wasn't on a podcast at all. It was actually at Starbucks. And I was at my first job out of college. I took, because I was married and had to take the very first job. They gave me a salary and that was $27,000 a year. I don't know if it was the first interview, but my very first Marine that I interviewed, we had Starbucks, was very, very good at doing behavioral interviewing. Tell me about a time you were under a lot of stress. Make sure that you're very descriptive. I want to hear names, places, I want exact details because I want to know like if you can handle line of 50 people out the door on this really high volume coffee shop that does 700, whatever people a day. So I asked this guy that question. He was like, how do you do under pressure? Can you give me an example of a time that you were under pressure and how did you handle that situation? He's like, well, I was the driver for the Humvee on the very first line that was going into Baghdad during Operation whatever, Desert Storm, whatever it was at the time. I was in the front line at night, whatever night, goggles everything and under fire and my tire blew out and I had to change a tire during this and I was just like, all right, just stop right there, I think you can handle coffee. So there's something about, I, I don't know if there's something that the military has taught you and what that goes in line with it, whether it being able to just, I don't know, take orders and execute on a plan regardless of anything that fails or goes wrong. But is there something about operations and it operations and in parallel with ex military experience?

**Drew Ludwick:** Yeah, I mean, I think there's a general level in the military of handling stress for sure. And whether it's intentional or unintentional, when you're in the military, you do have to overcome a lot. Flat tires without having a spare. Long days, long nights, trying to sleep on an airplane while you're transiting from one combat zone to another. I mean there's just that general level of stress that once you've been there and seen that it puts things into a certain perspective. So that's part of it, I think from the IT side, where we are forced to work with equipment that you think military grade, you think it's really cool. But in reality, military grade, sometimes it lags behind the civilian sector. Right. And they've gotten better about it. The military has adopted faster procurement processes and they're getting better stuff quicker now. But a lot of times we were asked and expected to do a lot with equipment that wasn't necessarily designed to do that, didn't have the greatest track record of maintaining and operating in those conditions. Along with that, though, there's. We do learn discipline around periodic maintenance checklist for everything. The military lifestyle is pretty regimented. So you do learn the discipline that comes with doing that kind of work, and it changes you. If I reflect on myself today and the guy that joined the army many moons ago, I see a difference for sure. At the end of the day, one of the things that sticks to my mind is we train and practice in peace so that we don't bleed in war. Right. And that's kind of a mantra that you train hard, you learn all the lessons in, in that environment so that when you have to do it, you're able to overcome those challenges.

**Phil Howard:** I have a lot of military friends and I think it's just a matter of. Because I practice Jiu Jitsu, I don't know what it is. I think it's just I end up with cops. It's interesting. Like sometimes the Jiu jitsu class, we have ex military guys, we have the cops and then we have the guys that just got out of jail. And then we all know each other and rol and have a great time. And I found that a lot of the ex military guys are like very, very kind and very, very calm. But if I ask them about. If I ask them about some stuff, sometimes they're just like, don't ask me about that. But I wanted to do. Do you have a reboot story or any stories that are technology aligned in combat where you were under a lot of stress?

**Drew Ludwick:** A reboot story? Yeah. It's funny you say reboot. So my last combat deployment was 2013. Time frame I deployed with this. It was a special operations joint task force. So I was working directly for a two star special operations general officer who was responsible for all of the special operations activities. So it was a pretty small and elite team. And something else that I found different, I guess about than what I expected about special operators is you think special operators, like, they just need their weapons and they go do what they do. Turns out they're pretty demanding on the technology side too. They really loved doing video teleconferences, for example, which going back to 2010, 2013, it was definitely possible. But we were doing daily battle update briefs, called them bubs, where the general would get on with all the different bases where he had forces and just talk about the operations from the night before and what they were going to do that night. Pretty important meeting. And I was the senior network engineer maintaining the infrastructure there on the base. And we had a couple different secure networks. We had the typical army or US Sipper. We had coalition network. We had a couple flavors of classified networks. I was working on another one that didn't have this call up on it at the time, and I got a little ahead of myself and maybe didn't have a good change management plan in place and ended up restarting the encryption device. Right. It was a device that was an inline encrypted everything over ip. And I thought I was restarting the one for this other network and I actually restarted the one for this network that was hosting this video teleconference with all the commanders around the theater at the time. And yeah, took it down. And that was a very traumatic event because the device itself took a couple minutes to restart and then you'd have to rebuild the calls. But what made things worse was there was a problem that we didn't know about with the device where if you rebooted it in a certain way, it dropped the encryption fill. So we lost our comsec in the device. And our comsec custodian was on the night shift, so he was asleep. And I mean, it took 30, 40 minutes to get the main classified network back up into our base because of that one button push. I learned a lot. You always talk about what you learn from those events. Right. And I accepted the blame. And the takeaway was, hey, this is probably close to a zero fail environment. We need some redundancy. So we ended up building some redundancy in. But it was a stressful way to realize we weren't redundant.

**Phil Howard:** Yes. What was happening in the meantime? 45 minutes for something to turn back up. Was it walkie talkies? And like, what was it?

**Drew Ludwick:** Well, I mean, we had unsecure comms, so we were not able to communicate out, but the call stopped. And that's when you get infantry and special operation colonels and generals sitting around staring at you because they're waiting for you to get the circuit back up. Right. That's not a comfortable situation.

**Phil Howard:** Were you guys using mostly like fixed wireless and point to points and stuff to communicate back then? Were people running cables?

**Drew Ludwick:** And by that time we were actually on a lot of fiber that we had run fiber kind of around the country. So we had fiber to half of our bases and there was a big fiber ring that ran that followed the loop road around the country. As we rebuilt the road, we were laying the fiber there and other than that, some satellite stuff for austere locations.

**Phil Howard:** Yeah, it's amazing how much the world is cabled. It's cabled more than people think. The fact that you guys actually cabled it, that's actually pretty interesting that you guys are running whatever dark fiber or something was there just like a whole crew of people that's just like, hey, you guys gonna run the truck and start laying the fiber? Were you like trenching it or was it on poles or. I'm just curious.

**Drew Ludwick:** I think it was trenched. I mean, like I said, they were one of the major infrastructure projects that the US did. There was building this huge ring road in Afghanistan that went all the major cities in Afghanistan. And. And while they were building it, luckily they. They laid fiber.

**Phil Howard:** Amazing. My cousin's a merchant marine and he was like, yeah, I don't think there's anywhere in the ocean that's not cabled. He was like, I think we know where every sub is. The only way we don't know where a nuclear sub is if it's completely shut down, just sitting there silent. And I was like, what about this and that? He's like, that's classified. Can't tell you.

**Drew Ludwick:** It's like, okay, yeah, yeah, that's crazy.

**Phil Howard:** So one of the other themes I think has come up a lot is it's hard to replicate. Maybe. I don't know if this is correct or not. Maybe the stress of an infantry colonel. Is that the right word? I don't know. All the different things like yelling at you while you're restoring communications. Does that environment teach you anything about business or that? Does it teach you something that no certification program ever could? Like, is there something that you're bringing to the table that military people bring to the table that, I don't know, you couldn't learn in a, I don't know, CSO training class?

**Drew Ludwick:** Yeah. I mean, it conditions you. Right? The military is about training the hardest way possible. Seeing the extremes crawling through the mud. The infantry colonel story is a funny one. I mean, you could reference an infantry colonel. And a lot of people probably have stories about them, yelling at them. But the one that sticks out in my mind is I was working for the NATO commander and one of his aides was an infantry colonel, West Point graduate. Right. The West Point being the Army, a military school. West US Military Academy at West Point. And very demanding, demanded certain kinds of pens be used. If we were building reports, if we were printing stuff out, everything had to be exactly right. Yeah. That particular colonel came down to our communications bullpen area where my team was, and I think kind of almost theatrically kind of tore me in half, literally ripped me in half about some sort of administration task. Right. Hey, your team isn't doing this. Right. So, yes. You, by being exposed to stress like that, you experience it, and then the next time it happens to you, it's not quite as traumatic. Right. Like, that's how the human body works. Right. So that's part of what the military does. Right. They expose you to these extreme situations and you become a little bit more kind of accustomed to that to a certain degree.

**Phil Howard:** Do people ever. Do people ever roll their eyes or does it become theatrical after time? Like, can you actually get fired from the military? Or. I mean, if you really screw up, like, what's going to happen? Like, if you just screw up, you're just an idiot. Like, what if you're just an idiot and you screw up and you're getting yelled at all the time, like, what happens? I'm just curious. Yeah.

**Drew Ludwick:** I mean, it depends who you are, what you're doing. I mean, if you kind of expect that with a private, you're going to yell at them and you're going to have to get them. That's part of that development process. A lot of most of them come through that. But, yeah, like, in a job like that, like, I. I would get fired and I would go have to go do something kind of less important and less thrilling.

**Phil Howard:** But is it good or bad from a civilian standpoint? Right. So a lot of people come back. At least that guy, by the way, that I ended up interviewing, that was like changing the tire in Baghdad. He ended up going back for three tours. No clue where he's at today. But he just like him. For him coming back to, like, the real world was like, I can't do that. There was something about, like, the civilian world and being over there was just like, I just, I can't. It was like I could just tell.

**Drew Ludwick:** They see a lot of people struggling. Right. Sometimes it's our difficult transition. I guess the other Point I wanted to make about that kernel, though, in addition to kind of that desensitizing you to the stress, you learn a lot about leadership, right? Like, to me that it was clear that was like a intentional act by this colonel to come down and not only dress me down, but do it in front of my own team just so they could see that he was pretty serious about whatever it is we were talking about. Right? That's a style of leadership, right? You learn a lot by seeing good leaders, bad leaders being exposed to that much in the military, your boss and your leader changes every year or two. You get exposed to a lot of different leadership styles and you can draw from that when you come out, right? You take the good, you take the bad, you adopt it to the type of leader you are and you want to be.

**Phil Howard:** I think if it creates the right positive change. Like me personally, I've worked in many different types of environments before. I've worked in an environment where it's like super, super liberal and you've got a 1, 800 number that you can call for HR department, if anything. And people are getting turned in for every little tiny thing like every now and then. And I found that environment to be much more. Less rewarding and stressful. I found it to be very passive aggressive, kind of this weird, stressful, kind of gossipy environment all the time. And then when I left and went to a, like a Cisco startup, it was almost military. I mean, it was like people being called out in front of like 200 people in a staff meeting, like, are you weak? Are you? I just remember like crazy. I remember like swearing. I remember all this wild stuff. And I was like, I can't believe they're swearing. Like HR would, would get called. And like, I remember just HR department kind of being like, just like this figurehead department. And I became a much better. It sounds weird, but like that environment, succeeding in that environment ended up being much more rewarding for me. I don't know what that means. And then. So I think there's a fine balance between telling people what they need to hear so that they can be successful versus, I don't know, maybe this weird passive aggressive, not telling them what they need to hear and being very, very sensitive to their, I don't know, psychology, which they don't actually end up growing in that case. And I don't think it does the person really any justice if we continue to let people thrive on their weaknesses and never overcome areas that they should strengthen. If that makes any sense.

**Drew Ludwick:** Yeah, no, I think it's valid. I think a lot of people appreciate the more direct style. At times. I look at leadership as like a rheostat dial, right? It's not an on, off thing. You don't just turn it on or off, but you kind of turn it up when you need to turn it down. Other times, and on the military side, I think there are times when you can turn it down. You can let people learn from mistakes, and you can let them kind of develop a little bit on their own. But there are other times when you need to crank it up because, hey, we need to. We need to take that hill, right? We got to go do this mission. We don't have time to talk about it. That's when you crank it up and you start yelling. And you got to be able to kind of, as a leader, you've got to be able to do that. But as the lead, as one of the team members, you've got to be able to know the difference, too. And when. When the time is right, just pick up your. Your rucksack and go do what you need to do.

**Phil Howard:** Being in the position that you're in now, and at the beginning of the call, you said you didn't expect to be in the position that you're in. How do you manage people now without replicating any type of toxic pressure or negative stress? Like, how do you balance between this kind of good stress and how do you manage people now? Having all the experience that you've had, what's the best piece of advice you have for someone that's new in the IT leadership role or in new and their leadership role?

**Drew Ludwick:** I think you nailed it, right? There's a communication component, right? You've got to be honest and upfront with your team and let them know that you're focused on the mission. You're not there to be their friend, their buddy, right? Like, you're getting paid to do the job of leading that team. You've. You've got to have some internal lines that you don't cross around being friendly, being too available. You've got to communicate those and just hold everyone to the standard. So what is the standard from an IT team perspective? You've gotta know what your business goals are, and you gotta clearly communicate those to your team and tell them kind of what your expectations are, and that becomes the standard. I think the minute you start kind of deviating from that and bending is when you kind of lose control and the team suffers, the business suffers.

**Phil Howard:** In commercial it, we have this thing that people have been dealing with for years. Right. And it's no one. It's unarguable that the landscape is changing ridiculously fast now. Not that it hasn't changed fast since 1970. It has. It's changed ridiculously fast because we didn't have Internet back then, which is still blows my mind. We didn't even have cell phones when we were kids growing up. Maybe we did. We had bag phones eventually. The IT guy used to be the dude that hid in the server room and had like little to no maybe ability to interact with humanoids. And now there's a transition where nothing in any business gets done without it touching it. And yet there's this transition going on where the 93% about IT leadership still sees their team as the help desk guys and not their team as the C suite. And there's a translation that needs to happen between highly technical IT nerd stuff and using that nerd stuff to drive the business forward as a business force multiplier. What's the biggest problem with IT getting heard at the executive roundtable and not just glossing people over.

**Drew Ludwick:** I think you're touching on a really relevant topic that we all kind of struggle with day to day is how do we get into all the right discussions we need to be in and make sure we're a part of it? Because I spent a lot of time in the military, 20 years in the military, spent about seven years working in IT infrastructure after that, and then a handful of years doing gaming and hospitality. And now I work in architecture, engineering, construction firm, doing IT for them. And all of those business sectors, they're very different. But I would argue most businesses today, their main product is actually data, right? What we're producing is data. What the business does is a certain type of data. Right? They're architectural drawings, construction drawing. We're doing a lot of energy work, but it boils down to data. So your point about the business really becoming more and more reliant on it is 100% accurate. It touches every corner of every company that I've been a part of. It's that dependence is expanding more and more. So the struggle is we're still in that period of time where the executive leaders, they came up in a different time when IT and technology, it was analog phones on their desks, computers that they used for specific functions, but maybe not for everything they did. And they've got to grow through that. So that the biggest struggle is making sure as IT leaders, that we're a part of almost every action and activity that's happening at the company because in some way it's going to draw on an application. It's going to require certain type of data storage and data protection. Are there reporting requirements with certain clients about data spillage or cyber activity? Right. Everything comes back at some point or another to technology. I'm pretty lucky. Today. I have executive leadership that's very supportive, but that's not always the case. Right.

**Phil Howard:** Is it just back to the kind of the military metaphor. How much of the mission were you guys given privy to? Or was it very compartmentalized and it was like you guys have to execute on this compartment of the mission, or did you have a very clear understanding of what we're trying to accomplish?

**Drew Ludwick:** Yeah, I think that's something military does pretty well, is they involve communications planning and activities, and they solve that with process. So the army doesn't do anything without an op order. Everything we do from a convoy to go pick up new trucks to driving starts with an operation order. Right. Part of every op order is a communications annex or appendix where at some level, some communication planners were involved. And they think through primary, secondary, tertiary comms. They're thinking through different scenarios. So the military does a very good job from a process perspective of involving communications in their planning.

**Phil Howard:** Overall reason why I'm asking that is like some of the biggest disconnect Is it being involved in really kind of like the main vision and understanding and mission of the business to begin with, and how is it helping drive that forward? And my assumption is the more car compartmentalized or the less involved it is in the mission and vision of the business to begin with, then the more of the department of it, they become the more of a cost center. They become the more of a, hey, guys, can you fix this crap and build this project and do this stuff for me? And theoretically, I think they become less of a business force multiplier for the business.

**Drew Ludwick:** Sure.

**Phil Howard:** We're trying to figure out, how do we become better business analysts and better business visionaries as IT guys and translate that into like the broader vision of the business?

**Drew Ludwick:** Yeah, I've seen it both raised in another role. I was on the receiving end of a lot of last minute, hey, we bought this new cool system. They're here to turn it on. And that might be the first time you hear about it. Right. And the risk is there's security risks. There's. Who knows if they may have gone to a trade show and seen some great display and they bought it right there. And they may not even get their components. They want Right. So that's the risk. The other side of that is being involved in business plans, building those relationships. So I think the way I approach that is, and this is something that was difficult for me and I imagine it'd be difficult for a lot of IT leaders because a lot of us are introverts. I still think of myself as an introvert. I'm probably happiest when I'm just again sitting on a keyboard in a router, jumping from one hop to the other and bouncing around networks. Right? That's my happy place. But you realize along the way that you've got to become extrovert to build those relationships. You've got to communicate effectively both with the executive team and your peers. Right? You've got to have a very good foundation. It's based on trust, based on experience. But you've got to build those relationships so that you're not reliant on the process, just working. Right. You may have a good process in place where systems are supposed to go through a, or formal process, but if you don't have those relationships and you're not working at those constantly, you're still going to miss things.

**Phil Howard:** I think some of the best business leaders in the world have been extroverts that have learned how to really, I think, solve a problem and I guess to your point, use data to solve a problem and, or grow a business. It's just a matter of how do we break down problems and how do we ask the right questions. You don't necessarily have to be the most outgoing person in the world. I think there's like a whole group of like sales professionals that are just known for being extroverts. Right. And everyone thinks of like the salesperson or the sales solution guys. It's like real outgoing, kind of stereotypical dude running around a party, shaking hands and taking people out to lunch and everything like that. But there's a whole group of people that are like really engineering minded, kind of really good at doing needs assessments and breaking things down. Which is really the type of like I think sales professional that you want is. You want someone that can really break down a problem and find the right solution for you, not someone that's just trying to sell you something.

**Drew Ludwick:** I think it's exactly true.

**Phil Howard:** So you've had a lot of experience at last across all different fields. You have a lot of kind of like you, you have telecom. Most itis don't have telecom experience. A lot are like, what is this telecom garbage? You have even like wireless experience as well. But You've got the military experience and kind of all this broad stuff is probably. Is really what's ended you up. Like you said, by mistake. We all end up. None of us really end up where we end up because we said we're going to be there someday. Somehow we've fallen into this. And I think 90% of the people that I've interviewed on this podcast have said, yeah, I kind of fell into it. I was an engineer and then I was this. And then back in the day, we didn't even have it as a role, and here I am. So what's the point of all this? For the listeners out there listening and people growing up in this world now, which is completely different, we've got AI and all kinds of other wild stuff. If someone was going to ask you nowadays, learning it, should I go deep or should I go broad? Like, what's the answer to that?

**Drew Ludwick:** Yeah, I generally, and I have these conversations pretty often. I tend to put people in a certain direction. Right. There are some pretty well worn paths at this point. Right. There's engineering, there's systems engineering, network engineering, there's project management, there's systems analysts. There's ways to go. And I maybe it's my own bias, my own background bias. I tend to think, like you've kind of, I think, said is those make the best leaders. Those are the. Those are the best salesmen. Those are the best, the ones I like to interact with the most. So I think the path I recommend is go get good at something, do what you enjoy, because if you're enjoying it, you're going to be more productive, you're going to be happier kind of throughout and see where it goes. Right. Life is funny that way. Right. Like, you could end up going in a different direction. A role draws you in a different direction, and you just didn't see it coming. But start with what you like to do. Get really good at it. I think that's fundamental. Right.

**Phil Howard:** I've seen. I don't know if you've seen this, but I've seen very ambitious young people, very talented, very smart young people, and just make mistakes. I don't know how else to say that. And I'm watching. I'm like, I've given people advice before. I was like, I think you should do this because this makes a lot of sense and this would make the most sense to your life just from like a number. From a data standpoint. Okay. From a number standpoint. And I've seen people that are very, very ambitious just spin their Wheels. And they're the people that I thought would probably get go the furthest and they don't. I don't know if I've ever seen that. And I don't know what is that mistake that they're making? What is the mistake that they're making? I don't know if we've ever seen that. And I've seen people that are just like real chill, just kind of like strong and steady, and they're just like. I'm like, wow, like, you're doing very well. Congratulations.

**Drew Ludwick:** Yeah, I mean, great. As you're telling that story, I was thinking of a team member I had a couple years ago. Right. I think his mistake was chasing the money. He was a technician. He was a support technician. Hands on, rolled out, fixed things for customers at their desks, whatever. He was pretty handy. He would come to me anytime there was a job opening in the department. We had a big department and there might be a project analyst position that was making a few more dollars an hour. He's like, oh, hey, Drew, I want to do this. I'm like, why? It's not. And then he'd come back a few weeks later. There was a system engineer role open. What is it that you want to do? Clearly he had a young child and a younger guy. I think he was more focused on chasing that money and that extra couple dollars an hour. And you see the same thing. People leave jobs all the time for an extra dollar an hour. Right. And it might not necessarily be the best situation, but they think that it's better to get that extra money and they could do the job. But my advice to him and anybody else is figure out where your passion lays and stay focused on that. Like I said, there are well worn paths if you want to be a network engineer. You can work certifications, you can work certain. We'll get you the experience. You want to just stay focused on that, and you're going to be a lot more kind of successful in the long run.

**Phil Howard:** I think when you've been around the block long enough, you'll find that there's not that big of a difference in 20 to $40,000 a year. Like, you'll find a way to spend that real quick.

**Drew Ludwick:** Oh, yeah, no, for sure.

**Phil Howard:** There's really not now $20 million. There might be a big difference between $20 million and that. I haven't experienced that difference yet, but I've noticed. I've told people, I was like, it's not worth, like, even if they offer you $20,000 bonus and an extra $20,000 a year. Like, really, really think about it. Because trust me, it's not that big of a difference. Work, life, balance, being somewhat comfortable, being able to breathe sometimes is so much more important. Even sometimes I'm just like, I'm shocked at some of the jobs and career jumps people make. And I don't know if it's. Sometimes people come and ask me a lot of advice, and I don't know why. To me, I'm just like, oh, isn't that just common sense? But maybe common sense just doesn't come common, if that makes any sense. And it's sometimes the job that you pick, you should just be really, really picky with the job and the next career junk you make. For me, I. I always wanted to pick a job where I knew I could be successful, where I could look at it, I could be like, okay, yeah, I can come in and make a big difference there. It's kind of like if you want to go take a new IT role, you go in, you take a look at the place, you're like, oh, there's like 15 old servers, they're on Lotus notes. They've got like, oh, I can make a difference here. You know, like, I'll take that job. Whereas you go into the job, it's like kind of everything's already pristine. The last guy got kind of fed up. He left. And there's just not much growth opportunity there. But the salaries there, you kind of just. You just kind of know. There's like this feeling that's like, this is going to be boring. And not. There's not going to be. It's going to be stale. I don't really know if you've experienced that, but that's my own. That's my thing when it comes to career stuff.

**Drew Ludwick:** Yeah. No, I mean, I've been around long enough now, too. I know what I'm looking for. Right. Culture is a big part of it. It's hard to be successful in it if the department isn't taken seriously. Right. So you need to think about those things. And the worst thing I've seen is, like, when people do come to us for guidance, but they've already made up their mind. Right. That's the hardest thing as a leader to get over is we've got a lot of information, a lot of experience that we can share. Sometimes this younger generations don't necessarily take it all in. I keep thinking about my own kids. They're the worst. Right. They don't want to learn. I wish as a Parent, you don't want your kids to make the same mistakes you've made and how many. Probably talked until I was blue in the face about, don't do this, go do this. Here's the reason why. And you just. It's hard to watch your kids or your younger co workers make those mistakes anyway, right? You saw it coming, and it's hard to overcome that.

**Phil Howard:** It's almost like the bad kids are easy to coach and the good kids are more difficult to coach because the good kids are, like, naive and the bad kids are just like. You're looking at them and you're like, oh, I can read minds, right? Why was your age one time, like, you know that I know you're hiding that over there. And they kind of look at you like, how do you know that? I'm like, you forgot that was once your age. And you think that I'm like an idiot, but I'm not an idiot. With that being said, training our kids, the thing that I want, what's all right, it's a kind of like a fear thing. Like, if I was to ask you, what are you most afraid of? What is a legit threat right now from the IT or is the legit threat? And I think that legit threat is the same thing that I want to train my kids to know. That's me. But if I was to ask you, what's the thing that keeps you up the most at night, and what is the most likely thing to happen that is going to put everyone out of a job or destroy the company or whatever it is? What's the most likely thing?

**Drew Ludwick:** I mean, there's a lot you worry about as an IT leader. I think the. Obviously the thing you're most worried about is a cyber attack, right? The nasty R word, right? Like that. That's something that'll derail a company. And have we done enough awareness training, right? Have we locked our systems down? Are there controls in place? There's everything that goes into that. And that's the easy answer, right? Like, everybody's afraid of cyber. That's just like, if you're just not paying attention. And I think we haven't talked a lot about AI. Probably wouldn't be an IT podcast if we didn't talk a little bit about AI. But I think something I worry about is, are we moving too fast? Are we out of control? AI is just getting turned on everywhere nowadays, right? How is our data? How are we protecting our data? Because again, I would argue we're a data company, right? Like, we've got to. Everything boils down to data. Are we doing enough to do a controlled AI rollout and are we protecting our data and have we built the foundation?

**Phil Howard:** Can anyone answer that? Other than the AI geniuses that built all of this and really know what's going on. I mean it's almost conspiracy theory esque. It's definitely conspiracy theory level of which we could go down a dark hole on everyone. Do we even know enough? I don't think we do. It's kind of like 100% we don't.

**Drew Ludwick:** Yeah, we don't know.

**Phil Howard:** My general thought is not learning it and not staying ahead of the curve is a bigger threat to than implementing it is my general thoughts. I think there's going to be outliers. I think there's going to be a few people that got some crazy super screwed hack. Like some really wild thing that's going to happen. I'm not saying that people aren't going to get. This is not talking ransomware. Everyone should be ready for all that stuff. I think that that's real. That's not a matter of if, it's a matter of when. Just depends on what industry you're in. Everyone should be aware of all that stuff. But when it comes to AI, I almost feel like the bigger risk is your staff and people not knowing it and not learning it than it is worrying about, dude, they're going to give our information out and screw us.

**Drew Ludwick:** Yeah.

**Phil Howard:** And that could be a horrible answer.

**Drew Ludwick:** No, I think it's really insightful and true. I mean we're all familiar with shadow it, right? The concept of if you don't provide a service to your user, they're going to get it somewhere. Right. I think that has been magnified as it pertains to AI. Shadow AI is happening everywhere. It's somebody on their phone now just dumping in company data without even kind of thinking about the second and third order effects of doing that. So if we're not teaching what is safe AI use, what kind of data is okay, what kind of data isn't okay? How do you get the best results? That we're putting our users at a disadvantage. We're putting our data at risk. Your point about not knowing what we don't know is right. The hardest part about AI, about deploying AI is building in that DLP and that data governance. Right. If you don't start with good data governance, any AI could be a bad AI. Right.

**Phil Howard:** If I was to ask you what's the most important data that needs to be protected and what's the data we don't need to worry about? I mean it depends on the company. But how do you answer that question?

**Drew Ludwick:** Yeah, I mean that's a question everybody should be asking theirselves is what data is the most critical will lead to the most reputational or financial damage to the company. Right. That's the data that you have to protect the most. And it is different for every company and it's going to vary. Right. Like, and I think I mentioned client requirements. Right. Every contract we sign with clients and customers and partners has requirements in it around how to safely handle data or will in the very near future. So who's tracking that? Right. Because that. Now you're talking about data that very high customer.

**Phil Howard:** Yeah, let's just hit the top three, like maybe top five most important data things like from a company internal department.

**Drew Ludwick:** Right.

**Phil Howard:** What are the ones that need to be locked down the most that are maybe most volatile to be used or leaked with. I don't know if it's AI we got. Well, let's throw the AI. Let's throw the AI portion in there. But I mean to me I think it's kind of obvious. It's like hr, it's customer credit card type of information, it's proprietary data. And healthcare, it's in healthcare files. But I mean, what are the ones that scare you the most?

**Drew Ludwick:** Yeah, personnel data is a big one, both internal and external. Right. Like if we're talking about AI. Right. Like if you don't have your own internal personnel data properly governed, you're potentially spilling internally. One employee is going to see data about another employee that they shouldn't. Right. That's just as bad as an outside actor getting access to that data. Financial data is the same way. Right. Like protecting our corporate finance data and any proprietary information. Today I think of internal engineering data around energy, for example, is there's thousands of lines of calculations that go into engineering energy projects. That's something the company has spent years and years perfecting. It's the magic sauce of the company for. Or the energy part at least. Right. Like that data is critical. We gotta protect it like it's Fort Knox gold. Those things you talked about, customer credit card data. Right. Like obviously that's important. Internal communications is critical. Right. The way a company talks internally can be harmful if it's spilled out. Right. So but that goes to the process of that data governance before. I mean in a perfect world, before we turn AI on, we've identified that data, we've got controls around it. It's properly labeled. We've got role based access controls in place around that structure. Right. That's how all of that should be in place before you turn on AI, before you turn on business intelligence. But sometimes we're playing catch up when

**Phil Howard:** communicating all this to executive management. Where's the biggest disconnect? What's the biggest disconnect that IT leadership has with the C suite or executive management?

**Drew Ludwick:** Yeah. You can't go stand in front of the executive or the team or the board and say, hey, we need to enable DLP and RBACs right away. Our data's a risk. Right. They're not going to know what the hell you're talking about. It has to be phrased and framed up in a business risk perspective. Either the risk to the business is such if we don't start labeling our data or to meet this business goal. Right. Again, knowing your business goals. To meet this intent of this goal, we have to start storing and structuring our data in a different way. It can't be an unstructured data pond. Right. We're going to warehouse it and get it organized and be ready for whatever. So it has to be framed single source of truth.

**Phil Howard:** Like a really good single source of truth for the company.

**Drew Ludwick:** Right. And again, single source of truth isn't going to mean much necessarily as much as like what's the risk to the business if we don't do that? Right. That's the only thing that is going to get the point home, I think.

**Phil Howard:** Okay, so is there a problem in commercial IT right now That's. Do you think that there's a problem that is generally unsolved right now? And generally what is there a generally like is there an unsolved mystery or an unsolved. An unsolved problem in commercial IT right now, other than the quantum computing, whether that's even real or not. Is. Is there a, a general problem that most people are having a, a very, very difficult problem to solve right now that if we solve that we're all billionaires and we sail off into the sunset? I'm going to start asking this for now because someone's going to have a really good answer someday and we'll be able to solve it?

**Drew Ludwick:** Yeah, I mean, we've talked about some of those problems. I mean the one we've talked about is getting the corporate mindset out of it is just there to give out laptops and get the conference rooms connected. Right. That's one that you hear a lot about.

**Phil Howard:** I guess if we had to slow back, if we had to take a step backwards to take two steps forward and you had a complete buy in from the C suite for that. What would be the first thing, like if you, what would be the first project that you would take on? I guess we're going to, we're to slow down, we're going to stop everything. We're going to do this first.

**Drew Ludwick:** Yeah, I mean, I guess one that I've seen, it's not sexy or exciting. I think the next big security risk is around vendor management, right. I don't know that we've got a great handle on managing the vendor risks and that could be maybe a whole separate podcast. But when I look at vendors, you have to think of them in terms of them being partners, right? Like you gotta rely on them to do your business. We talked about AI, right? So today vendors turning AI on built into their applications and their systems, sometimes without proper notification. There's a lot of risk around cyber threats. We had a vendor recently that was compromised and business email compromise came out of that pretty quickly. So right now that's kind of the wild west, right? I don't feel like there's a lot of structure around that. I don't feel like there's a lot of good ways to kind of mitigate that risk.

**Phil Howard:** It's very, very difficult because the average mid market company has anywhere between 80 to 140 applications. And if you think about every single one of those applications that we use, how many employees are at each one of those companies that have access to your company somehow, not to mention the turnover of the staff at all of those different companies. So it's really a matter of kind of like which ones can we layer that have the most access or most impact on whatever it is company data of ours. If company data is the most important thing, what of those applications are touching our data and or physical humans at those companies? I can tell you from an Internet perspective, just because I've been in Internet for a long time and done a lot of networking and stuff. I can tell you that there's been numerous times where I've seen Visio maps and IP addressing completely shared very easily without any type of verification that I was not the IT manager calling in because I was trying to help my CTO get an RFO for an outage because there was an ice storm that took down and cut a bunch of fiber lines. But I can tell you that there was very little to if none verification of who I was. And that's just past experience of just knowing that. And it's like, how often can you call into a vendor and their customer service line doesn't do a very, very good verification of something if that goes in line with what you're talking about.

**Drew Ludwick:** Yeah, I think that's absolutely a part of it. Right. Like, we have to hit the belief button that these partners are doing everything they need to do to secure our data. Secure their data. It's a big risk.

**Phil Howard:** Where can people find you, follow you and reach out today if this conversation resonated with them?

**Drew Ludwick:** LinkedIn. Good home. I spend some time on LinkedIn.

**Phil Howard:** Any famous sayings or quotes that you like to say all the time to your team?

**Drew Ludwick:** One of my favorite sayings goes back a few bosses now is and it really applies to everything we do is you have to get comfortable being uncomfortable. I think that kind of sums up what you need to be doing every day. If you're sitting in your job and you're finding yourself too relaxed, maybe that's a problem. Right? You're not pushing yourself enough. If you're not pushing yourself and your team, you're not improving. So that's one of my favorites.

**Phil Howard:** One of mine, too. I save it to my kids all the time. I actually have a letter from one of my daughters that was saying, dad, after all these years, I'm really appreciative that you used to say, get comfortable being uncomfortable because it's the only one. We push ourselves out of our comfort zones that we actually grow all the time. Remember, I can remember my first boss that told me that along with helping people, having to know when to coach people, when to yell at them, when to give them the colonel yelling, to give them the colonel yelling. And that's usually when their bucket's full and they're very, very high on themselves and they're being very, very successful. Don't give them the colonel yelling treatment when they are their bucket's empty and they just started in the roll. Ludwig, thank you very, very much. It has been an absolute pleasure. You have been heard.

**Drew Ludwick:** Thanks, Joel. Appreciate it. Love the.

# EP421 Drew Ludwick Transcript

**Phil Howard:** All right, welcome, everyone back. We've got Drew Ludwig, cio, IT Leader with a very, very exciting pass. Why don't you introduce yourself? IT Director, Operations. I mean, a really nice history. Wendell company has given me just the background of where you're at right now and kind of what's going on.

**Drew Ludwick:** Yeah. Thanks for having me on. I love the show. Super excited to be here. So, yeah, today I'm the IT Director for Architecture Engineering company based in Buffalo, New York. Really more of a CIO role. It's a great opportunity to kind of leverage some of that experience. Some of it's fun, some of it. Some of it not so fun that you kind of referenced. But it's a lot of fun being able to kind of own the whole IT practice. Right. And be more strategic. Right. So if we talk about my background, I come from a very technical background. You could call myself the Accidental cio. Right. I never envisioned I'd be sitting in the big chair one day. I was much more of a network engineer, keyboard warrior. My passion was crawling through networks, building and maintaining networks. The tougher the environment, the better. And I just. I love doing that, and I guess kind of my path kind of brought me here today. So, yeah, I think from a leadership

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