Deep Drive: ERP and Lifelong Leadership Lessons

Mark Putnam

Good afternoon, Olivia. Today we’re digging into why working on an ERP rollout—whether it’s Workday or one of its many cousins—isn’t just a technical marathon. It’s a crucible. A pressure cooker for leadership, culture, and personal growth.

Olivia Carter

Hey everyone! I love that you used the word “crucible,” Mark. Because most people hear “ERP” and their eyes glaze over. They think spreadsheets, training videos, and painful status meetings. But the real story? It’s how these projects confront the human side of change. You’re not just installing new software—you’re asking people to rethink how they do their jobs. That’s harder, scarier, and way more personal than any technical upgrade.

Mark Putnam

Exactly. Years ago, I was interviewing for a CIO role, and during a lunch with the president’s senior team, the executive VP turned to me and asked, “Why is a student system implementation so difficult?” And I said, “Because it’s not just a system. It’s your institution’s identity, encoded in software. Every student system reflects the mission, strategy, and quirks of the place it serves. When you try to change that, you’re not just rewriting rules. You’re asking people to let go of how they’ve always worked.”

Olivia Carter

That’s such a key insight. And yet, when things go sideways—when timelines slip or resistance flares up—people default to blaming the technology - IT dropped the ball or “The system doesn’t work.” But so often, it’s not a tech failure—it’s a leadership gap. It’s a culture issue. And once you realize that, you get a whole new set of tools to work with. It’s not about fixing a bug. It’s about building trust, clarifying decisions, and helping people step into a new way of working.

Mark Putnam

Exactly. And once you start to see it that way—as a human problem, not just a system one—you can’t unsee it. It changes how you lead, how you listen, and how you design for change that sticks. That’s when the real progress starts.

Olivia Carter

So, let’s talk about ambiguity. ERP work yanks you out of your comfort zone—constantly. There’s no script. No autopilot. You’re being asked to make decisions with incomplete information, under pressure, while everyone’s watching. And you can’t just freeze. That’s where trust comes in, right?

Mark Putnam

Absolutely. One of the hardest lessons in ERP work is that clarity doesn’t always mean certainty. You have to lead even when things are murky. And the instinct is often to project confidence, to say, “We’ve got this.” But real leadership in that moment is about saying, “Here’s what we know, here’s what we don’t, and here’s what we’re doing to figure it out.” That kind of honesty builds trust faster than any polished presentation.

Olivia Carter

Totally. I had this flashback to a faculty meeting during a new student system rollout. Tensions were high, and I could feel the room bracing for a sales pitch or some top-down directive. Instead, I just opened with, “Look, there’s a lot we don’t know yet. Here’s what we’re trying to understand, and here’s what we need from you.” And you could feel the mood shift. People leaned in. Instead of venting, they started offering ideas. That moment of vulnerability built a foundation for real collaboration.

Mark Putnam

That’s it. When people feel like you’re leveling with them—not spinning, not glossing over gaps—they respond. It’s not about being the expert. It’s about being the one who can hold the space for uncertainty and still move things forward.

Olivia Carter

And I think that’s what makes ERP work so formative. It forces you to get comfortable leading in the gray. You’re coordinating across functions, with competing priorities and evolving requirements. There’s no perfect answer, and if you wait for one, you’ll stall the whole project.

Mark Putnam

Exactly. And here’s the kicker: trust doesn’t come from having all the answers—it comes from how you show up when you don’t. If people trust your intent, your process, and your follow-through, they’ll stay with you—even when the road gets bumpy.

Olivia Carter

That's right, Mark.

Mark Putnam

Let’s talk governance. If you want to succeed in an ERP project, you have to become fluent in how your institution actually makes decisions—not how it’s charted on the org structure, but how things really move. That means navigating committees, councils, stakeholder groups, and all the messy, layered realities of shared governance.

Olivia Carter

Right. And it’s easy to dismiss that as bureaucracy or red tape, but it’s not. It’s the terrain. You can’t bulldoze through it. You have to walk it, map it, and build relationships as you go. And that often means showing up in rooms where your presence isn’t required—just to listen, learn the players, and start building coalitions before the big decisions hit.

Mark Putnam

Exactly. I remember a crisis-room meeting—one of those moments where everything felt like it was about to come apart. People were tense, the timeline was slipping, and there were competing demands on the table. But here’s what made the difference: we had the right stakeholders in the room, and we’d already done the groundwork. There was enough trust to have the hard conversations without spinning out. That wasn’t luck. That was weeks of showing up, listening carefully, and understanding how decisions really get made at that institution.

Olivia Carter

And that’s where leadership presence really matters. Governance is the structure, but presence is the posture. It’s how you show up in those rooms. People pay attention to who’s calm under pressure, who’s prepared, who listens more than they speak. That’s how you become the person others look to—not just because of your title, but because they trust you when it counts.

Mark Putnam

Yeah, presence isn’t about commanding the room. It’s about anchoring it. When a project hits turbulence—and every ERP does—people remember who was steady, who stayed engaged, and who helped keep things moving without panic. And if you show up that way enough times, you start getting invited into the conversations that really shape the institution.

Olivia Carter

Okay, so every ERP meeting is basically a negotiation, right? You’re balancing interests, scope, resources—sometimes it feels like you’re herding cats and juggling chainsaws at the same time. Everyone’s got strong opinions, and the stakes always feel high.

Mark Putnam

That’s a vivid image, but you’re not wrong. The real shift is moving from classic project management—just checking boxes—to program management. It’s a different mindset. You’re not managing tasks, you’re managing value over time, across silos, across personalities, across changing priorities. And negotiation becomes the operating system of your day.

Olivia Carter

And it’s not just the big, dramatic showdowns. It’s the subtle stuff—how you run a design session, how you frame tradeoffs, how you handle tension when two departments want incompatible outcomes. That’s where real negotiation skills show up. You can’t strong-arm your way through it. You have to listen carefully, ask better questions, and help people get to what actually matters.

Mark Putnam

Exactly. I remember a scope debate where Finance wanted tighter controls, and HR wanted more flexibility. It looked like a zero-sum standoff. But we paused, dug deeper, and uncovered a shared concern around audit risk and workflow clarity. That led us to a solution that served both teams better than their original asks. But it only happened because we stopped arguing positions and started clarifying interests.

Olivia Carter

That’s where tools like tactical empathy and calibrated questions come in. You have to slow the conversation down just enough to really hear what’s behind the ask. A lot of times, the right solution isn’t even on the table until someone makes space for it.

Mark Putnam

Right. And this is where negotiation meets leadership. You’re not just looking for a middle ground—you’re creating forward momentum. You’re helping groups navigate uncertainty without retreating into silos. And that’s what a good program manager does. They don’t just manage deliverables. They stitch together alignment across time, function, and personality.

Olivia Carter

And once you start thinking that way, you realize ERP success isn’t about who wins the meeting. It’s about who can build something that lasts—something that works for more than just one department or one cycle. That’s the long game.

Mark Putnam

Let’s talk about institutional literacy. If you don’t understand how your university actually works—its budget model, academic structure, research priorities, and governance flow—you’re flying blind. ERP projects force you to get into the weeds. You sit with Finance to understand payroll calendars. You meet with HR about position funding. You learn how academic appointments work, how grants flow, how tuition gets charged. And by the end of it, you leave with a map of the institution’s real operating system.

Olivia Carter

Totally. And that map changes how you lead. Because now, when someone says, “That’s just how we’ve always done it,” you can ask why—and actually understand the answer. But hand-in-hand with that is what I’d call digital simplicity. I learned this the hard way. Early in my career, I worked on a legacy system integration that was, honestly, a mess. We bolted on so many exceptions and workarounds that no one could keep track. When something broke, it was like playing digital Jenga—pull one piece and the whole thing would shake.

Mark Putnam

Been there. Complexity is seductive. It gives everyone what they want in the moment, but it sets you up for long-term fragility. ERP projects teach you that simplicity isn’t a compromise—it’s a strategy. The true innovator isn’t the one who builds the most features; it’s the one who reduces friction. Who designs for clarity, for scale, for institutional memory. Especially in higher ed, where staff turnover is real and institutional knowledge walks out the door every year.

Olivia Carter

Right. And once you’ve been through a messy implementation, you start to advocate for clean, integrated solutions by default. You push back on exceptions. You ask, “Is this truly essential?” Because you’ve seen what happens when complexity goes unchecked—systems become brittle, training becomes impossible, and no one trusts the data.

Mark Putnam

Exactly. These projects force you to grow up professionally. You stop chasing customization and start designing for sustainability. And more importantly, you start to see how technology can either support or hinder the core academic mission. That perspective stays with you. It shapes how you approach every decision after go-live.

Olivia Carter

And that’s the real leadership skill here—learning how to say no to clutter, yes to coherence, and aligning digital tools with institutional purpose. That’s not just IT strategy—that’s stewardship.

Mark Putnam

That's right, Olivia.

Olivia Carter

Let’s shift gears to AI. ERP projects are a crash course in learning how to treat AI as an ally, not a threat. You see firsthand how predictive analytics, automated workflows, and smart notifications can actually make people’s jobs easier—if you introduce them the right way.

Mark Putnam

Exactly. And the key is subtle: it’s not about dazzling people with flashy tech—it’s about solving real problems they already feel. If someone is drowning in manual reporting or chasing down approvals, and you show how the system can automate or streamline that, now AI is solving their problem, not just adding noise.

Olivia Carter

And that’s where leadership really matters. Because most teams aren’t anti-AI—they’re just skeptical. They’ve seen tools overpromised and underdelivered. If you come in with empathy and clarity, and show them how AI can help them do their job better—not replace them—you start to shift the whole narrative.

Mark Putnam

Totally. It’s not just a tech conversation, it’s a trust conversation. People need to know you’re not here to cut headcount or devalue their work. You’re here to enhance their impact. That requires leaders who can translate institutional problems into solvable patterns—and then use AI in service of those solutions, not in pursuit of novelty.

Olivia Carter

Right. That’s the difference between responsible AI adoption and what I call “dashboard theater.” You’re not just chasing shiny objects—you’re solving for meaningful outcomes. And once you lead through that kind of rollout, you carry those skills into every other project.

Mark Putnam

And ERP is the perfect training ground for that. You’re already redesigning processes, so you have the chance to bake in AI intentionally—not as an afterthought. And when you do that well, you model a mindset that says: “We use technology to amplify people—not replace them.”

Olivia Carter

That's right, Mark.

Mark Putnam

So, let’s bring it home. ERP projects are fertile ground for mentorship and for developing the skill to frame organizational risk. I’ve seen rising IT leaders step up in these environments—coaching peers, building trust with executives, and learning to embrace uncertainty rather than run from it.

Olivia Carter

I love that. Some of the most lasting impacts aren’t the big, flashy wins—they’re the quiet moments where you help a colleague see the bigger picture or coach someone through change fatigue. That’s how you build institutional resilience. And honestly, that’s what sets transformational leaders apart. They don’t just survive change—they help others grow through it.

Mark Putnam

Mentorship is leadership. And learning to talk about risk in language executives understand—financial, reputational, mission-driven—that’s how you build credibility. You create a trust ledger, and over time, people trust you with bigger challenges.

Olivia Carter

And that’s the real payoff. It’s not just about getting to the go-live, it’s about who you become along the way. These projects change you, if you let them.

Mark Putnam

Well said, Olivia. That’s a good place to wrap for today. Thanks for joining me for this conversation.

Olivia Carter

Thanks, Mark. And thanks to everyone listening. We’ll be back soon with more on tech, leadership, and the real work of change. Take care!

Mark Putnam

Goodbye, Olivia. Goodbye, everyone.