Deep Dive: The Quiet Work of Great Leaders

Olivia Carter

Okay, so mentorship—let’s talk about it. Why do people love to act like it’s this big formal thing? Like, you need a program or a playbook to make it happen?

Mark Putnam

Right, but that’s exactly the problem, isn’t it? We’ve turned mentorship into this mechanical idea...structured pairings, scheduled check-ins. None of that truly cultivates growth the way actual, day-to-day leadership does.

Olivia Carter

So you’re saying we, uh, we’ve overcomplicated it?

Mark Putnam

I think so. The real mentorship—at least in my experience—happens more organically. It's, um, it’s watching great leaders navigate challenges, seeing how they engage with people, solve problems, even how they hold themselves accountable. You learn by observing and absorbing, not by sitting down at a scheduled mentoring session to “talk about leadership.”

Olivia Carter

Yeah, that’s so true. And honestly, when I think back on jobs I’ve had, the best “mentors” weren’t even called that. It was just bosses who, like, really cared. They cared about the work and about you getting better at it.

Mark Putnam

That's right. And it’s that investment and example-setting that shapes you the most. I’ll never forget one of my early bosses. He didn’t just delegate tasks and leave me to it. He worked beside me, sweated the details with me. You start to unconsciously adopt those behaviors—you absorb them.

Olivia Carter

Hmm. And what if you’re working for someone who’s not exactly...inspiring?

Mark Putnam

Well, you have two choices at that point. You either find a way to still learn something—which, let’s be honest, can be tough—or you look for someone better. It sounds harsh, but who you work for can define your trajectory more than you realize.

Olivia Carter

So, thinking about great leaders and how they shape us got me wondering—what about hiring those people in the first place? Like, what actually makes someone a great hire? Because it feels like people obsess over résumés and credentials, but does that even really matter?

Mark Putnam

You know, it’s funny. In my experience, some of the best hires I’ve made weren’t the ones with the most polished résumés or advanced degrees. It’s about something you can’t always list on paper—drive, curiosity, the ability to learn quickly.

Olivia Carter

That makes sense. So you’re looking for people who... what? Just show up with potential you can build on?

Mark Putnam

That’s right. Potential and mindset. I had a boss once who took a huge chance on me when, frankly, I didn’t even have the right credentials for the job. But because he saw my willingness to learn—and my hunger to succeed—I was able to grow into the role. That kind of chance, it stays with you.

Olivia Carter

Okay, but isn’t that a risk? Like, what if the potential doesn’t pan out?

Mark Putnam

It is a risk, sure. But I think the bigger mistake is hiring based solely on skills and experience and overlooking the right attitude. Skills can be taught—mindset, not so much. And part of that mindset is cultural fit. When someone aligns with the values and vision of your organization, that risk becomes a lot smaller.

Olivia Carter

Alright, so let’s say you’ve hired the right people. How do you actually build trust with them? Like, what makes a team...actually feel like a team?

Mark Putnam

Routine, structure—those little things that create clarity and alignment. I’ve always held weekly meetings with my staff, and let me tell you, those meetings can make or break a team. It’s where you sweat the details, solve problems together, get everyone moving in the same direction.

Olivia Carter

Wait, wait, hang on—you’re saying weekly team meetings? People hate meetings!

Mark Putnam

Well, yeah, if a meeting is just...empty updates that could’ve been an email, of course. But what I’m talking about is much deeper. It’s about building alignment and trust. When meetings are intentional, they become where the real work happens, and strong culture forms around them. I’ve been surprised to discover that many executives in higher education don’t engage in regular meetings with their entire team.

Olivia Carter

Okay, I see it. So, it’s like trust comes from... shared effort?

Mark Putnam

Exactly. Leadership isn’t just about telling people what to do. It’s about rolling up your sleeves and showing you’re in it with them. That’s how you earn trust, and that’s how culture grows—through mutual effort and accountability.

Olivia Carter

Hmm... and what happens when someone joins the team who maybe doesn’t have that alignment yet?

Mark Putnam

Well, that’s where it gets tricky. Sometimes, you can coach someone into alignment; other times, you have to make tough calls. But it all ties back to one thing: clarity. Clear goals, clear expectations, and clear communication. It strengthens teams and filters out misalignment over time.

Olivia Carter

Building trust and alignment makes sense, but it’s got me thinking—what about stretch assignments? Why do leaders think it’s okay to give someone a task that’s, like, clearly beyond their skillset? Isn’t that kind of setting them up for failure?

Mark Putnam

It might feel that way at first, but think about it from another angle. Growth only happens when you’re, um, pushed outside your comfort zone. If you’re waiting to feel “ready,” you’re, well, probably not growing.

Olivia Carter

Okay, but where’s the line? Like, isn’t there a risk of giving someone too much too soon and totally wrecking their confidence?

Mark Putnam

There’s absolutely a balance. That’s where guardrails come in. You don’t just—throw them into the deep end without a lifeline. But, here’s the thing: when people are given room to try, to stumble even, and then recover... that’s where real confidence comes from.

Olivia Carter

So you’re saying some mistakes are, what, necessary?

Mark Putnam

That’s right. A mistake handled well can be the best teacher. I had a situation early on where I made a pretty big oversight—a security vulnerability. When I realized it, I thought, "That’s it, I’m done.” But my boss didn’t panic. Instead, he treated it as a learning experience, and honestly, it’s one I’ve never forgotten. It shaped how I approach problems to this day.

Olivia Carter

Wait, let me get this straight—you messed up, and instead of flipping out, your boss was just like, “Oh well, great learning experience!”?

Mark Putnam

Not exactly that casual, but yeah, pretty much. He trusted me to fix it, and that trust was everything. It taught me more than any training session ever could have. Stretch assignments need that trust built in, or they just don’t work.

Olivia Carter

Hmm... I guess I can see how that changes things. If someone believes in you enough to let you try—even if you don’t nail it at first—that’s huge.

Mark Putnam

It is. And for early-career employees, those moments set the trajectory. It’s almost like, if you’re afraid to give a little responsibility early on, you’re, um, missing the chance to grow a future leader.

Olivia Carter

But do you have to keep an eye on them, or is it hands-off once they’re in the deep end?

Mark Putnam

You have to stay present—not hovering, but there. It’s about finding that balance between autonomy and support. When people know they’ve got room to experiment, but someone’s there to back them up, they grow faster, and they grow stronger.

Olivia Carter

And when they, like, totally knock it out of the park?

Mark Putnam

That’s the best part. You’ve just shown them—and your whole team—what’s possible when someone is genuinely empowered. It changes how they see themselves and their potential.

Olivia Carter

You’ve made a good case for how trust is essential to stretch assignments. It’s got me thinking—how does that same idea translate to strategic alignment in higher ed? Like, on a practical level, what does that even mean?

Mark Putnam

That’s a great question. In higher education, deans carry a heavy load—they’re responsible for enrollment, faculty, fundraising, even student success. They’re at the core of what makes a university function effectively.

Olivia Carter

So, like, they’re juggling everything?

Mark Putnam

Pretty much. And if you’re in a leadership role, particularly in technology, your job is to, um, make their work easier, not harder. That means aligning your tech strategy with their needs and the institution’s overall mission.

Olivia Carter

Okay, but, uh, how do you actually build that alignment? Because IT and academia don’t always, let’s say, speak the same language, right?

Mark Putnam

Exactly. That’s where intentional engagement comes in. For me, it’s about regular conversations—not just when there’s a crisis or when you need their approval. I make it a point to meet with deans routinely, sometimes monthly, sometimes quarterly, to hear what they’re dealing with and where technology can help.

Olivia Carter

So, it’s not just about IT supporting academia; it’s about IT really understanding it first?

Mark Putnam

Right. Technology isn’t just a service—it’s a partner to the academic mission. And that partnership only works when there’s trust. Building trust takes consistency. You show up, listen, and then deliver on what you say you’re going to do.

Olivia Carter

But how do you, like, measure if that trust is actually there?

Mark Putnam

You know it when deans start coming to you proactively, asking for your input before they make big decisions. That’s when you’ve moved from being a transactional resource to being a strategic partner.

Olivia Carter

Okay, but let’s be real—alignment sounds great and all, but isn’t it exhausting to constantly meet with people and check in?

Mark Putnam

It can be, but honestly, it’s what makes the whole system work. If IT aligns with the deans, the university moves forward faster. And if they’re not, no amount of flashy tech projects will save you. Alignment is the foundation everything else builds on.

Olivia Carter

You know, talking about alignment and trust makes me think—what about when there’s an added layer of complexity? Like, for women or people from underrepresented groups, leadership sometimes comes with extra scrutiny or different expectations, doesn’t it?

Mark Putnam

Absolutely. And it’s not always overt, but it’s there. It can be double standards, assumptions, or just extra barriers to being heard. It’s one reason why leaders have to be intentional—not just aware of those challenges, but proactive in supporting and advocating for every member of their team.

Olivia Carter

Yeah, but how do you even start to do that? Like, beyond just knowing it exists?

Mark Putnam

Well, it starts with empathy—understanding that what you see on the surface often isn’t the whole picture. Some leaders carry hidden burdens, and recognizing that can change how you, you know, approach mentorship and support. It’s about creating space for people to thrive, even when the playing field isn’t always the same.

Olivia Carter

Right, and I guess that ties into what you were saying earlier about trust? It feels like trust would matter even more when you’re dealing with those extra layers.

Mark Putnam

That's right. Trust is the anchor—the thing that lets people push past those challenges because they know you’ve got their back. And that trust isn’t just nice to have, it’s, um, essential if you want to build a team or organization that genuinely thrives.

Olivia Carter

Hmm. It’s kinda like... leadership is less about the big moments and more about how you show up for people in the everyday stuff, right?

Mark Putnam

That’s a great way to put it. Day-to-day actions define the culture and the trust you build. And honestly, it all circles back to something simple but foundational—loving the place you lead. If you don’t feel that genuine care for the organization, the mission, and the people, it’s hard to lead effectively.

Olivia Carter

Okay, but what if you’re somewhere you don’t feel that connection? Like, what’s the move then?

Mark Putnam

Honestly? You’ve gotta ask yourself if it’s the right place for you. If the work doesn’t inspire you—if you can’t bring your best effort—then maybe it’s time to find a place that does deserve it. Life’s too short to lead without passion.

Olivia Carter

Wow, okay. That’s a mic drop moment if I’ve ever heard one.

Mark Putnam

Well, it’s the truth. Leadership isn’t just a job—it’s a responsibility. And if you can love the place you lead, that shows up in everything you do. It becomes contagious, for better or for worse.

Olivia Carter

Alright, well, I think that’s a perfect note to end on. Thanks for, you know, sharing all your insights. It’s been such a great conversation.

Mark Putnam

Likewise. It’s been a pleasure.

Olivia Carter

And that’s all for today’s episode of "Dispatches from an Internet Pioneer." Take care, everyone, and we’ll catch you next time.