IT MATTERS Podcast
Apr 21, 2026
On this episode of the IT Matters Podcast, our host is joined by Troy Penny, Global Vice President of Information Technology at Harsco Rail. As a children’s book author, Troy has learned a lot about the power of storytelling in technology. Together, him and our host discuss the influence of leadership and culture in IT, aligning business with technology, and the importance of stories in a quickly-changing technology landscape.
Conversation Highlights:
0:00 Introducing Troy Penny, Global VP of IT at Harsco Rail
[12:08] Learning Leadership in IT
[17:15] Growing from IT Challenges and Failures
[22:01] Connecting Strategy, People, and Technology
[29:42] Finding Your North Star
Notable quotes:
“Great technology leaders don't just think in system frameworks, they think in stories.” - Keith Hawkey [01:13]
“You have to look at IT through the eyes of the business.” - Troy Penny [16:34]
Connect with Troy Penny:
https://www.linkedin.com/in/troyspenny/
Read Troy’s books:
https://www.amazon.com/stores/Troy-Sheridan-Penny/author/B0F7LSBM8Y/allbooks?ccs_id=b434535d-3802-4e17-8639-015db6324679
Aaron Bock
Welcome to the IT Matters podcast hosted by Opkalla. We're an IT advisory firm that makes technology easy for your business. Our vendor neutral technology advisors work directly with your team to assess technology needs and procure the best IT solutions for your organization. On this podcast, expect high level expertise from our hosts, plus experience driven perspective from the leading experts on topics like AI, cyber security industry focused IT solutions, strategy and more. Now let's get into today's discussion on what matters in it,
Keith Hawkey
and welcome to the it matters. Podcast hosted by Opkalla. At Opkalla, we help IT teams understand the busy marketplace of technology strategy and services with a data driven approach. On this podcast, we invite technology leaders to discuss the challenges facing the modern IT department. My name is Keith Hawkey, technology advisor at Opkalla, and today's guest is someone who embodies the idea of great technology leaders don't just think in system frameworks. They think in stories. I'm joined by Troy Penny global, Vice President of it at Harsco rail, where he leads the global IT strategy. Troy also has spent his career operating at the intersection of enterprise scale, public sector transformation and leadership development, advising senior leaders modern, modernizing complex organizations and teaching the next generation of project and IT leaders. But here's where Troy really stands out, alongside publishing serious IT leadership and leadership books. He's also an author of children's stories about cats that go on adventures and occasionally saved the world. So today we're going to talk about enterprise, IT leadership, governance and strategy, but also creativity and storytelling and why the ability to explain complex ideas simply might be one of the most underrated skills a technology leader possesses. Troy Penny, welcome to the it matters.
Troy Penny
Podcast, Thank you, Keith, it's my pleasure.
Keith Hawkey
So before we begin, Troy, there's your tradition on the it matters. Podcast, where we play two true, two truths and a lie. Have you ever heard of such a game? I have, and since you have a unique background and have written a couple children's books in recent years, I thought, why not do two truths and a lie around the OG children's book author, Dr Seuss, okay, how familiar are you with the life of Dr Seuss?
Troy Penny
More familiar with his works than his life? Okay?
Keith Hawkey
Well, I think this is mostly about his work, so we might be in good shape. So two truths and a lie. So you are trying to identify the one lie out of these three options. So let's start the first one. Dr Seuss created the word nerd, which first appeared in if I ran the zoo. Second, Dr Seuss wrote all of his books standing on one foot to keep the rhythm playful. Number three, Dr Seuss wrote Green Eggs and Ham using only 50 words after accepting a bet that he couldn't write a book with fewer than 60 you. So those are three options. I can re read them if you'd like.
Troy Penny
No, I think the lie is probably composing his books on one foot. I just couldn't imagine doing that.
Keith Hawkey
You're correct, Troy, there's no, no knowledge that Dr Seuss wrote his books on one foot, however, much to my surprise, he apparently created, invented the word nerd,
Troy Penny
which I had I had heard that, or thought I had heard that before, and and when you gave that as the first option, I thought to myself, I think that's true, and it surprised me also when I'd heard it the first time now, and as far as the 50 words in Green Eggs and Ham, that doesn't surprise me. I actually used green eggs and ham to teach my first child how to read, because they're. So few words in it, and the words are repeated so often, that he began to recognize the shapes of words. More so than sounding out the word ham, he just knew what the word ham looked like. So he got to where he could read a combination of memory and pattern recognition most of that book at a really early age. So that part didn't surprise me.
Keith Hawkey
Yeah, well, you, you're successful in identifying the lot. I maybe I should make these a little bit more, a little little harder. Writing on one foot, I thought writing on one foot with a book like green eggs in hand. This 50 words wouldn't be too much of a battle, but there's probably a lot that goes into that he'd have. He'd have some sore ankles, for sure.
Troy Penny
Yeah, it certainly sounds like the kind of thing you could imagine him doing, especially if you're familiar with his books. But, but I thought having written a little bit myself, I just couldn't imagine being very creative in that stance.
Keith Hawkey
Yeah, that's a so let's, let's dive into a little bit of your story. Troy, what can you tell us, a little bit about how you got into it, some of the early days. How did you get get on this trajectory, this career directory?
Troy Penny
Well, I actually began college at a high school on a music scholarship, and there came a point in time where I had sort of an epiphany, that I'm either going to be a famous musician or a high school course teacher. And I thought the latter was far more likely, and that didn't align with kind of where I saw myself, so I left the music department, and when I did that, I lost my scholarship, so I joined the military to help pay for the remainder of my college, which it did, and I ended up spending a little over a decade in the US Air Force as an electronic warfare systems technician, and what we did was jam radar, which doesn't have a direct civilian application. Most airports don't want someone to jam their radar. So what I could translate however, was the engineering and technology skills involved in that career field. And at the time, this was the early 90s, I got out after the the Desert Storm campaign, and at the time, it had only just begun to separate itself from engineering, and it was still very, very hardware technical as well as well as software technical. Personal computing wasn't much of a thing, yet everything ran through big data centers. So it seemed to be the right fit for me as a civilian. And started out really doing just technical documentation and some ingress programming, and then worked my way up. I was fortunate to catch that technology curve in the 90s that sort of culminated in Why 2k and the.com era and all of that. And I was able to move up through the profession, and found that I really enjoyed it.
Keith Hawkey
So midnight, 1999 December, 31 What were you doing? That's, that's the big question in my mind.
Troy Penny
I was relaxing because I didn't believe planes were going to fall out of the sky. Probably the worst that would have happened was your bill wouldn't get printed, or you would receive a bill that showed you were 100 years overdue for something most machine systems weren't, I don't think, as vulnerable, and maybe I was naive, but they didn't appear to be as vulnerable as some of the stories would have led you to believe. Plus, I think, thanks to the people at Gartner, we had pretty good preparation for it, a good runway to to to get the critical systems up to date. So I felt pretty good about it. We had replaced our legacy ERP system at Johnson Controls, is where I was at the time, and, you know, we felt pretty confident that that the new system was going to perform, so I wasn't too bit out of shape about y 2k
Keith Hawkey
you mentioned Gartner in that equation. I so I'm 37 years old. I wasn't I was young when y 2k was a thing. Certainly wasn't in my career. How did Gartner help promote. Pair organizations. I'm curious about that.
Troy Penny
So I don't know the whole story, but I do know that they were one of the early identifiers of the Y 2k bug, and they had forecasted at the time, I think, almost a trillion dollars in global remediation that was necessary. And Gartner has that niche in projecting future technology and various pitfalls and things you needed to prepare for. And they were probably the premier analyst for y 2k and a lot of people would consider them maybe a little bit of a fear merchant at the time. But I think, you know, they rightly pointed out that people have been very short sighted and how they program date fields using a two integer Date field. So they were probably at the forefront of advising remediation plans and contingency plans and that sort of thing, and certainly were in a leadership role in both identifying and helping to resolve the problem.
Speaker 1
Yeah, that's, that's a fact. How has Gartner been around?
Troy Penny
You know, I couldn't, I couldn't tell you, Keith, probably 40 years. Yeah, I'm just guessing,
Keith Hawkey
yeah, I'm most familiar with Gartner when it comes to the magic quadrants and how they rate vendors as that's very near and dear to what I do during my, you know, for my day job. But going back to your your career, you've been in IT leadership for a lot of your career. What experiences do you think is foundationally shaped the way that you approach it leadership today?
Troy Penny
That's a good question, and you know, so many of them are really woven together to make anyone who they are today. You're a sum of your experiences, but there's a couple of things that stand out. And one, I think, was fairly early on in my career, when I was implementing an ERP system for a manufacturing organization that had several plants in a corporate office, and the corporate office, as they often do, made the decision for the plant community that they had to implement an ERP system. And until then, each of the plants sort of had their own homegrown manufacturing systems that were exquisitely tailored to exactly how they did business and a custom made suit, if you will. So they were naturally, I think, a little resistant to having a one size fits all common core system forced to fund them. And as the leader of that implementation, I found myself in the position of having to convince these stakeholders to get on board, because we needed their input. Obviously, we needed to understand their requirements, and needed to make sure that they were engaged in the project. And that was a little bit of an eye opening experience coming from the military. If you're given a directive, it's passed down by a series of orders, and people salute and obey the orders. In the corporate world, it was a little bit different. You had stakeholders with a lot of both formal and informal power within the organization, and a plant manager is, as you probably know, is very much the king of their their own feudal kingdom there and runs that plant and runs everything about it, and knows everything that happens there. So these were powerful individuals, and I needed to get them on board. I met with one of the plant managers. We'll, we'll call him Tony, it's not his real name. And when I went in there, I immediately was met with a cold shoulder, with a resistance I was the enemy from the corporate office coming to force this thing upon him, and I, the first day I met with him was really a little bit of a disaster. I felt like we far from having a meeting of the minds. We've had sort of an adversarial conversation. So I was there for a few days at the plant. I came back the next day with a little bit different an attitude, and tried to see. It through his eyes, and frame it from his his point of view. So the second day, I said, Tony, everything you said to me yesterday makes sense. I thought about it. I think there is a lot of risk involved with this. I need you to help me identify what these risks are, and to help me go to these other plants and identify their risk so that we're making sure that that you don't have something foisted upon you that isn't going to work, and that we're protecting your key functions and your key capabilities you have. So that really turned him around. I think, knowing that I was looking at it from his perspective, and by recruiting him to help me with this, I think it, it changed his attitude a little bit. And he eventually sort of became the plant champion on the project, and I found more and more him sort of shifting sides a little bit to where he was becoming the ERP champion, also to the plants and helping to communicate, to gather requirements, to identify risk, to come up with mitigations with all the other plant managers. He became an invaluable ally on that project. And I think what I took away from that, and how that shaped me was an early learning that you have to look at it through the eyes of the business. You can't approach it as a technologist, maybe you can to a certain level, if you're just coding from a design specification or something, but if you're going to be in leadership, you have to be a business person, and you have to think like a business person, and you have to understand that the deliverables you create all have to tie back to capabilities that are important to the business, and ultimately those tie back to to a strategic objective somehow. So it was a, I think, a key learning I had early on, even though it was probably the hard way to learn
Keith Hawkey
it, you bring up a great point, Troy and and that a lot of the evolution since the early days that you started managing it was very hardware focused, very technology focused. The further you advance your career, unlike, well, I guess there are some, there are some career paths are like this, but it's particularly striking in technology, where you really are married to the technology, and you love technology, and that's why you're in the business. To you are only as valuable as your relationships within the company. At some level, it's your your personal relationships with being able to bridge the gap and meet such a plant manager that enabled you to accomplish your mission, able to com, accomplish the project. I certainly think that's one of the that's one of the skills that most IT leaders that are getting in, that are starting to get into leadership, maybe they become a manager, and they're trying to become a director of it and move up. It is one of the hardest skills to learn, especially if it goes against your personality, because a lot of the times you think that you're getting into technology, to be away from people and to be closer to computers, right?
Troy Penny
Yeah, I've had, I've had developers work for me in the past that honestly love what they did. They wanted to have their hands on the keyboard locked in a room writing code, and that's fine. I mean, that was their niche, and that's what they love doing. But I tell my people, if you ever want to be in a leadership position, there comes a point we have to start thinking like a business person, and and it doesn't mean you you give up your skills, necessarily, but you add skills to those, and at some point, you become more of a coach and a mentor and a teacher and a translator to the business. Then you are a technologist. You have to be able to make that evolution,
Keith Hawkey
I'm sure in your your your career, there's been a time or two or an IT initiatives gone off the rails as
Troy Penny
well. Oh sure.
Keith Hawkey
Like, here's what, what failed first, the technology, the process, the people, what did you learn from it? What's, what's, what's the memorable experience of something going awry.
Troy Penny
So you know when, when something goes off the rails like that, it seems like it's rarely the technology and processes. You know, processes are as good as as they're fit for, for the culture they're in. Processes really reinforce proper behavior. But. But proper behavior sometimes has to be adjusted. You can't always go back to a process. So in the early days of it, we didn't have great processes, particularly for projects. I mean, our models for projects were basically the NASA model that got us to the moon, and everyone thought that was pretty good, and we followed those things as closely as we could, but NASA was a government organization with unlimited money, and once again, they had directives that vendors had to follow, et cetera. It was a little bit different in business where your assumptions are different, and some of the decisions you make early on in a project can come back to haunt you if they're the wrong ones. I was working for a company that had a series of tugboats that went up and down the Mississippi River towing barges, and they were headquartered in Nashville, Tennessee. And the people in Nashville needed to know where these boats were and what they were doing as close to real time as possible. The current process had the vessel captains filling out log books, like every boat captain does, and then mailing copies of the log to Nashville, which was okay, but Nashville was getting real time events A week later, and really didn't have the visibility they wanted to the activities of the vessels. So we developed a satellite tracking system that we would adopt to work on the vessels themselves, and a computer console would be put on the bridge of the ship. And then for every log event that the captain had, we assigned it a code. So if you got gas, you typed in 150, if you dropped off a barge, you typed in 323, there was a different code for every activity you did, went through a lock, changed rivers, etc, and we had talked to the captains a little bit, but really never let them see The system that we thought we were getting their input, but what we didn't get was hands on, real-world engagement with the system and the first boat I remember like it was yesterday, we put the the computer console on the bridge of the ship that was about 10 o'clock at night, and we turned on the monitor, big, red, white and blue, company logo flashed up and immediately destroyed the captain's night vision. So he had to get the first mate, or whoever he was, the other guy, back from below decks to take over on the bridge while he went to a dark room and restored his night vision for some period of time. It never crossed our minds something like that, because it's something that we didn't deal with in our environment. So we had to go back and reprogram everything in red and black, you know, submarine colors, so it was low light and would protect night vision, so the vessel pilot could see the river at night. So it was a little bit of a reset for us. And the lesson learned there was we thought our stakeholders were the people in Nashville, the corporate people. They're the ones that wanted this capability. And we thought we would gather some requirements and get some knowledge from the captains of the vessels and the pilots of the vessels, but we never engaged them to the extent that we should have to really understand their jobs. And the lesson learned from that is the people who set strategy aren't the people that do the job every day, and those people matter in how a system is designed, how the system is used, what the constraints and controls in the system have to be. So you have to engage everyone. You engage them to the lowest level, because that clerk out there that no one thinks about is doing something specific that the Vice President will never even consider when he gives you his requirements. So it really taught me a lot about stakeholder engagement and how inclusive that needs to be to develop a good solution for a business
Keith Hawkey
that reminds me of two of the books that you have written on it, achieving the Nexus. Sustain the Nexus. Do you discuss any of these stories and in either of your either of your books? That seems that's definitely one of the more interesting it stories that I've heard Troy, to be honest.
Troy Penny
Yeah, well, it's, it was a school of hard knocks, which, you know, always tell people it's a great school, but the tuition is really high. That's right. So, yeah, I allude to that. I believe in the first book that particular story, the the first book achieving the Nexus. The word Nexus just means connection, or sort of a causal melting of two things, excuse me. And what I was looking to communicate with that is that you have to achieve that connection with the business as an IT organization. I kept seeing the same pattern repeated across different companies and teams where the IT teams would work incredibly hard deliver a major system. And on paper, everything looked great. The project was successful, but the business didn't end up really getting the value it expected, and what they did get wasn't persistent. So the central idea of this first book is that real success happens when the strategy, the people, the processes and the technology all meet, and if one of those is weak, you may be able to deliver a project, but you're not going to sustain results. So it's all about achieving alignment with the business, sharing goals, sharing ownership, sharing risk, understanding how the benefits chain connects from the lowest level deliverable all the way up to the strategic objective, and how it can enable functionalities that help an organization achieve objectives, but only if they understand them, and only if They have a seat at the table and play that catch ball with the various functional areas within the business, to understand their pain points, understand what they're trying to achieve, and be able to communicate how technology might enable them in doing that, I rely heavily on a lot of Peter Drucker's ideas there that organizations that you know share values and behaviors and beliefs are probably more successful even than those that that rely entirely on formal processes, because, again, a process is a means to an end. It's important. I mean, it trains people, it creates consistency, as long as they're followed. But you can't write a process for everything. Eventually, people are going to face ambiguous situations, situations that may be unpredictable, and they really have to understand how the business works, to know when to deviate or when to turn right or left on a project.
Keith Hawkey
Yeah, now that's that's I think it's incredibly important. It's funny enough. It makes me think a lot about my own company, upkalla, and how we look for technology advisors that meet a cultural fit above everything else, honestly, and when you're looking for the the professionals that are going to be servicing your user base and going to be really going to war with you, Troy, I mean, you want that right mindset that probably goes above and beyond any other process and is that first mode of action?
Troy Penny
Yeah, it's really all about culture. Keith, it's a culture of alignment, and it's also a culture of excellence that you want to create. And culture is it's like chemistry. People talk about it. They know it when they see it, but it's so difficult to achieve it. And to me, a good culture is created when it's it's agnostic to who's leading it anymore. People can come and go, but the culture persists. You see it in sports organizations like the Boston Celtics or the New York Yankees that had these internal cultures that just transcended players as they came and went, the organizations were still excellent. And I think it's it's very similar to how you instill values in children. You can't prepare your children for every situation they'll encounter. You can't give them the right answer to every question, but what you can do is instill a core set of values in them that will enable them to make the right decision. Education on their own, even when they're faced with a unique situation and culture within an IT. Organization is all about establishing those core values of alignment with the business, of ethical practices, of collaboration, just a set of things that become institutionalized
Keith Hawkey
and speaking of culture, I'd love to hear more about the culture of these adventure cats that that are saving the day when they feel like it.
Troy Penny
So I never saw myself as a children's book writer, and honestly, it was kind of accidental. I used to make up stories about our cats and tell the grandchildren stories about all these crazy adventures they would go on. And it's sort of almost the same thing as we're talking about before, because these are two ordinary cats. They're They're brothers, they're there. They talk in the books. So they're a little anthropomorphic, I guess, but they have been given a set of sound values in their home about courage and curiosity and loyalty and leadership, and, you know, doing the right thing even when it's hard to do it. And as they're thrown into this world of pirate ships and ghost ships and evil wizards and everything else they encounter, it's probably a cross between Indiana Jones and Johnny quest. Maybe what they encounter, you know, they run into some crazy situations for two ordinary house cats, but again, they rely on their values. They always come back to what's the right thing to do. They always trust each other. They always work together. And the culture and values they have usually end up having them make the right choice to get out of situations. So I'm not trying to be heavy handed or lecture children, but I want them to accidentally learn things not only about values and culture, but also a little bit about geography and some you know myths, and you know legends and things like that that I try to weave into the stories. Everything in the stories has a basis. At least in myth, I didn't make up any of the places they go or or situations they run into, they all have a basis somewhere, so I'm hoping that they can read a good story and be entertained by it, but accidentally learn something along the way.
Keith Hawkey
And there's three books today. Is there three or two?
Troy Penny
There are three. They're waiting on getting the illustrations finalized. As I was writing the books, I was kind of drawing my own pictures, and then later, towards the end of the last book, I experimented with using some AI image generation. Wasn't really happy with the results, so I had to hire an illustrator, and she is working on completing the illustrations for the books. I'll probably release all three of them at the same time, once the illustrations are complete, probably later this year.
Keith Hawkey
Well, we'll make sure to update the show notes on this podcast, to link that then Deborah Troy and we're coming up on time. Really appreciate the time you spent with us this afternoon, and with the incredible storytelling and finding out with your you know, your other passion, passion with fighting for the younger generation. Is there anything you'd like to leave with, is there a message that you think is not that would differentiate the successful technology leaders from the rest we have a younger audience listening sometime.
Troy Penny
Well, a lot of what I said I think helps to differentiate successful leaders. I think culture values, people, business, alignment, all those things are critical. But if I had to think of one thing that's often overlooked, I think it's understanding what your North Star is. Understand what what is guiding your business. If someone asks you, Why are you in business? The answer you'll hear most often is to make money, to create shareholder value, all those kinds of things. But maybe I'm often left field here, but I've always kind of considered those things necessary byproducts of what you're really doing. Think about it. Why does a hospital. Will exist. They want to make money, but they really exist to provide good care for patients and improve the quality of life for people that need doctors. Why does Harsco rail exist? Well, we're here to provide safe, reliable, environmentally sensitive infrastructure that supports transportation of people and products all over the world. If you look at that as the reason for your existence, that means something that's more than just hitting a revenue number. It motivates people. I think the way a profit target never will. It gives importance to your job, and that's everyone in the company, from the security guard up to the present president. So I would say that understanding your North Star, and even if, if you're not in business, if you're in business for yourself, if you're retired, if you're still looking for the right job. What is your personal North Star? What? What is the reason you're doing what you're doing? Is it to have a family? Is it to you know, improve yourself? Is it to you know, reach a certain freedom in life? So whatever that North Star is always keep it in mind and always keep centered on it, and let that be your guide. Let that be your your measuring stick for everything you're doing.
Keith Hawkey
It's incredibly well said. Troy, again, really appreciate your time. Encourage everyone listening to find your North Star, and we will see you next time on the IT Matters podcast, Thank you, Keith.
Aaron Bock
Thank you for listening, and we appreciate you tuning into the IT Matters podcast for support assessing your technology needs. Book a call with one of our technology advisors@opkalla.com that's opkalla.com if you found this episode helpful, please share the podcast with someone who would get value from it and leave us a review on Apple podcasts or on Spotify. Thank you for listening and have a great day. You.