Episode 30 Jon Elinsky

In this episode of Servant Leader’s Library, we sit down with Jon Elinsky, Director of Technology at LearnQuest, to explore how critical thinking and servant leadership go hand in hand. Jon shares his journey from tech innovator to team builder, offering insights on empowering people, challenging norms, and leading with authenticity. Whether you’re in IT, leadership, or just passionate about growth, this conversation will leave you rethinking what it truly means to serve.

Episode Transcript

Nicholas Paulukow
All right, welcome to another episode of Servant Leader’s Library, where we explore the principles, practices, and people shaping the future of leadership through service.

I’m your host, Nicholas Paulukow, CEO of ONE 2 ONE, a managed IT and cybersecurity firm, and today’s conversation is going to be a wild ride through the bold ideas of critical thinking—and a little bit of Android aspiration. Joining us is someone who says he almost has the nerve to call himself a visionary. He’s the Director of Technology at LearnQuest, a relentless out-of-the-box thinker, and a man who questions everything—not to be difficult, but to drive innovation, insight, and excellence.

He’s a husband, father, and in his own words, an aspiring Android—which is a title that covers a lot of ground. We’ll learn more about that today. With a career that spans a wide range of roles and organizations, he developed an uncanny ability to cut through complexity, elevate situations from every angle, and craft solutions that actually work.

Today, we dig into what it means to lead through questions, how operational excellence meets creative disruption, and why the best leaders don’t just serve their teams—they challenge them to grow. So buckle up and get ready for a conversation that might make you see your leadership—and maybe even yourself—a little differently. Let’s get into it.

Jon Elinsky, welcome! Can you tell the audience a little bit about yourself? This is great.

Jon Elinsky
Hello, Nick. Thanks for having me.

Nicholas Paulukow
Absolutely.

Jon Elinsky
This is very cool. I’m also going to bring you guys with me next time I try to have a job interview because that was like the greatest intro I’ve ever heard. I love it.

I don’t know if anyone has ever described me anywhere close to as cool as that, but that’s great. So thanks for that.

Nicholas Paulukow
Absolutely. Absolutely.

Jon Elinsky
As far as who I am—yeah, I’ve been doing technology and development mostly for like 30-something years.

Nicholas Paulukow
Wow. Okay.

Jon Elinsky
Ever since I was a kid, really. I was lucky enough to get in at SAP when I was—what year was that? I was like 22.

I did some temp work with them for their marketing show they do every year. It’s really big. And back in the ’90s, stuff wasn’t so automated.

So they needed to bring in, you know, “slave labor kids” to help run the tech room. Well, I mean, we sat in a double cubicle with five or six people for about two months, working on all different CEOs’ presentations. They would send us rough drafts, and we would clean them up, logo them, and prep them for showtime.

We also went down to the show in Orlando and made sure the breakout rooms were ready, the machines worked, and the speakers had what they needed.

Nicholas Paulukow
Okay. That’s neat.

Jon Elinsky
Yeah, it was cool. I had messed around with computers since I was a little kid, but I’d never done anything like that until then, and it was a great experience. I learned a lot and was around some really cool people.

The folks at SAP who did this were part of the Communications Media Team, which included the public website team and internet team.

So I was exposed to web technology—something I hadn’t been around much before. Hanging around them for all those months and seeing all this new stuff, I thought, “This is cool.” And I’m a pretty aggressive self-learner.

Nicholas Paulukow
Right.

Jon Elinsky
And I thought, “I can do that.” So when the temp job ended and I was unemployed, I went out, bought some books, and taught myself web programming.

Then I called them back up and said, “I know how to do this now. Give me a job.” And they did.

I ended up staying for five years and was leading the Internet team by the time I left.

Nicholas Paulukow
Wow. That’s amazing.

Jon Elinsky
Yeah.

Nicholas Paulukow
There was talk about an interview, right? You figured it out—just sign me up.

Jon Elinsky
Sort of. I was lucky enough to get to know a lot of people there. Knowing people matters.

Nicholas Paulukow
Right.

Jon Elinsky
They already knew my work ethic and everything else. I just had to say, “Hey, I have skills now to offer,” and they brought me in.

Nicholas Paulukow
Wow.

Jon Elinsky
I was still kind of junior—an apprentice or assistant—but it was definitely cool. I learned a lot from that team. They were very skilled, very friendly, and helpful.

I owe a lot to my experience there because I learned from everyone I could.

Nicholas Paulukow
Wow.

Jon Elinsky
Very cool about it. Strangely, over time, a lot of them left, and the team kind of fell apart. At one point, it was just me and the graphic designer left—even the manager was gone.

So we rebuilt the whole team. We hired new people and had a fresh start for the second half of my tenure.

Nicholas Paulukow
And how’d you go from SAP to where you’re at now?

Jon Elinsky
Well, I was still young. I didn’t have a lot of experience with how to navigate a giant multinational corporation, especially one headquartered in Germany. And I have a lot of strong opinions.

That didn’t always work out so great in corporate America. That hasn’t really changed—but I wouldn’t change it either. I champion that.

Jon Elinsky
Most of the development I’ve done has been in back-office environments—service departments, essentially. We were enabling other people to do their jobs within the company.

I took that responsibility seriously, advocating for those we supported and for the tools I was building. However, given that I was only about 22, working among seasoned SAP developers, my approach didn’t always land well. For instance, their internal mail program didn’t have word wrap, and I—perhaps too boldly—suggested it should.

I had strong opinions and voiced them, which wasn’t always appreciated, particularly coming from someone so young. Even today, while I’ve matured, my directness isn’t universally welcomed depending on the audience.

Nicholas Paulukow
I gotcha.

Jon Elinsky
But I definitely have strong opinions. That’s ultimately why I left SAP.

Nicholas Paulukow
It sounds like it offered a lot of learning opportunities, though. It must have been valuable technically, but also in leadership and professional development.

Jon Elinsky
Absolutely.

Nicholas Paulukow
Right.

Jon Elinsky
From a very early age, I was exposed to a significant number of management-level professionals within a massive corporation. I even worked at their newly opened headquarters during my tenure.

I had numerous role models—some better than others—from whom I learned not just technical skills, but also professional standards, leadership principles, and organizational dynamics.

Nicholas Paulukow
It sounds like it gave you a strong foundation to build from.

Jon Elinsky
It truly was a valuable education. I don’t have a lot of formal education; most of what I know is self-taught or acquired through hands-on experience—the proverbial “school of hard knocks.”

After leaving SAP, I found myself unemployed. I had always wanted to pursue search and rescue, and given I had some severance pay, I took a class in it. I loved it and turned out to be quite good at it.

Eventually, I became an apprentice instructor after further certifications, and my chief instructor, Eric Martin, taught me a great deal about leadership.

Nicholas Paulukow
Do you still do that today?

Jon Elinsky
I don’t, and I miss it terribly—more than anything else I’ve done professionally. I was primarily a rope rescue instructor and truly loved it.

Nicholas Paulukow
I can relate. I used to be in fire service, and that yearning to serve and engage in hands-on, critical situations never really goes away. Working alongside dogs in search and rescue especially fascinated me—the partnership is remarkable.

Jon Elinsky
Yeah, the bond between canine handlers and their partners is truly impressive.

Nicholas Paulukow
So you went from SAP to search and rescue instruction. How did you transition from that into your next professional chapter?

Jon Elinsky
I didn’t leave search and rescue entirely—it was never a full-time career. On the East Coast, most rescue operations are done through fire departments, not private sector efforts, and the private classes I taught weren’t enough to sustain a living.

Thus, I went back into tech, working for another German company, Phoenix Contact, in Harrisburg. During that time, my schedule was grueling—working all week, driving hours to teach search and rescue on weekends, then returning to my weekday tech job.

Nicholas Paulukow
Wow, what passion!

Jon Elinsky
It was exhausting but fulfilling. In my tech cubicle, you’d find images of Everest ice climbs, not tech diagrams—definitely not fitting the mold of the typical IT worker.

Nicholas Paulukow
It probably gave you a much-needed reset from the abstract nature of tech problems.

Jon Elinsky
Absolutely. It broadened my perspective—being exposed to drastically different environments enhanced my understanding of both fields. Leadership is better informed when you’ve worn multiple hats and operated in diverse conditions.

Nicholas Paulukow
That’s very true. Tell me about your current role—you’re now the Director of Technology, right?

Jon Elinsky
Correct. I’ve been at LearnQuest for over 11 years, which is as long as I’ve stayed anywhere. Initially, I led the development team, adjacent to IT, but following recent organizational changes, I now oversee all technology—including IT, development, and related systems.

Nicholas Paulukow
A big leap.

Jon Elinsky
It is. I had always been IT-adjacent; now I’m fully immersed.

Nicholas Paulukow
Welcome to the deep end!

Jon Elinsky
That’s my style—jump in headfirst. It’s earned me the family nickname “Black Diamond,” stemming from my first kayaking experience—taking on Class IV and V rapids with zero prior experience.

Nicholas Paulukow
Jump in and survive—that’s leadership too.

Jon Elinsky
Exactly. Sometimes the best way to learn is immersion.

Nicholas Paulukow
How has your leadership style evolved as you’ve stepped into these larger roles?

Jon Elinsky
Two pivotal moments come to mind: first, when I took charge of SAP’s Internet team at a young age—suddenly responsible for people I hired. That realization of responsibility transformed my perspective.

Second, becoming a search and rescue instructor. Teaching forced me to truly understand leadership—it’s one thing to perform, another to enable others to perform.

Nicholas Paulukow
You really have to master the material to teach it.

Jon Elinsky
Yes. And beyond skills, you have to guide people through fear, doubt, and resistance.

Nicholas Paulukow
So when you lead today—especially in a fast-paced IT environment—how do you maintain a servant leadership mindset?

Jon Elinsky
For me, servant leadership means empowering others. It’s about enabling my team to succeed—not micromanaging, but removing obstacles. Most one-on-one meetings end with me asking, “What do you need from me? How can I help?”

Nicholas Paulukow
You’re guiding the raft downstream, not paddling it for them.

Jon Elinsky
Exactly. They still have to navigate, but I clear the debris where I can.

Nicholas Paulukow
Critical thinking is clearly part of your leadership toolkit. How do you apply questioning without it coming off as criticism?

Jon Elinsky
It’s important to clarify the intent behind the questions. I tell my team: questions aren’t challenges; they’re checkpoints to ensure success. Communication must remain open and non-threatening.

Nicholas Paulukow
In IT, where speed is critical, how do you balance urgency with empathy?

Jon Elinsky
By emphasizing that mistakes are inevitable and acceptable. I publicly acknowledge my own errors to normalize imperfection. It builds trust and reduces fear-driven behaviors.

Nicholas Paulukow
And how would you define “servant leadership”?

Jon Elinsky
Servant leadership is about empowering and supporting your people, not ruling them. I despise the “Darth Vader” management style—fear-based leadership is toxic. I aim to build environments of trust and authenticity.

Nicholas Paulukow
Any story that particularly shaped your views?

Jon Elinsky
My early experiences in search and rescue. Witnessing volunteers put everything on the line selflessly, while others sought status and recognition, left a deep impression. True leadership comes from service, not self-promotion.

Nicholas Paulukow
Absolutely. What’s your definition of success today?

Jon Elinsky
Success means my people feel safe coming to me with problems. Trust is the ultimate metric of leadership effectiveness.

Nicholas Paulukow
And now for some rapid-fire questions. Ready?

Jon Elinsky
Let’s do it.

Nicholas Paulukow
Fill in the blank: A great leader always…

Jon Elinsky
Is authentic.

Nicholas Paulukow
Favorite leadership book or idea?

Jon Elinsky
A Brené Brown book—my wife recommended it. The focus on vulnerability in leadership resonated with me.

Nicholas Paulukow
Advice to technical leaders stuck in old management styles?

Jon Elinsky
Trust your people. Listen to them. You’re not the team—you are there for the team.

Nicholas Paulukow
Perfectly said. Jon, thank you for joining today. Your insights on critical thinking, service, and authenticity have been truly valuable.

To our listeners, if this episode sparked something for you—don’t keep it to yourself. Share it, rate it, and let us know. Until next time, remember: leadership isn’t about being in charge—it’s about taking care of those in your charge. Keep serving, keep leading, and we’ll see you next time.

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