DSE team AI training
Leading from the Frontier: Or, How I Convinced My Team to Follow Me Into the Unknown (And We All Survived)
The Moment of Doubt
Picture this: It’s 11 PM on a Tuesday. I’m on my third coffee. My screen is full of code that may or may not be working—honestly, at this point, I’m not entirely sure. I’m learning about agentic AI systems and Model Context Protocol, and I have that familiar feeling that every technical leader knows: the one where you’re simultaneously excited and terrified that you might be leading your team off a cliff. The responsible thing would be to stop, do more research, maybe wait until things are clearer. I kept going anyway.
The Comfortable Trap
Here’s what you need to understand about leading Visa’s design system engineering team: we’re really, really good at what we do. My team builds component and pattern libraries in React, Angular, Flutter, CSS. Beautiful, documented, production-grade UI engineering that thousands of developers depend on. We’re the bread and butter people. The reliable ones. The “we’ve got this” team. And there’s something seductive about that kind of competence, isn’t there? You can spend an entire career getting incrementally better at something you’re already excellent at. Safe. Predictable. Comfortable. But I kept having this thought—more of a nagging feeling, really—late at night when I couldn’t sleep: Is bread and butter enough for what’s coming? I didn’t want us to be the team that was amazing at yesterday’s problems. I wanted us to evolve into a holistic product engineering team. One that could build diverse applications across our ecosystem. One that would be ready—actually ready—for this AI-native world that’s clearly not waiting for anyone to feel prepared. The question was: how do you transform a team without breaking what makes them great?
The Terrifying Decision
I made a choice that felt equal parts courageous and completely ridiculous:
I would go learn it myself first. Alone. Nights and weekends. Before telling anyone what I was doing.
Because here’s the truth about leadership that nobody really likes to say out loud: if you’re not willing to look foolish while learning something new, you have absolutely no business asking your team to do it.
So I enrolled in “The Complete Agentic AI Engineering Course” on Udemy and dove in.
And let me tell you—I was bad at it.
The Learning Curve (Or: A Humbling Experience)
You know that feeling when you’ve been a director for years, and you kind of forget what it’s like to be a complete beginner at something? Where you don’t even know what you don’t know? Yeah. That. I spent weeks fumbling through tutorials on building agents. Breaking things. Fixing things. Breaking them again in new and creative ways. Staying up too late trying to understand MCP protocols while my brain screamed at me to just go to bed already. There were moments—many moments—where I thought, “What am I doing? I’m supposed to be leading a team, setting strategy, being the adult in the room. Instead, I’m debugging agent configurations at midnight like a junior engineer.” But that’s exactly what I needed to understand. If this was hard for me—someone technical, motivated, with time I could carve out—what would it be like for my team? Would they find it valuable? Would it connect to our actual work? Or was I chasing shiny objects while calling it “innovation”? I needed to know before I asked them to invest their time and trust.
The Discovery (And the Relief)
Plot twist: the course was phenomenal. Not just “this is interesting” phenomenal, but “oh, this changes everything” phenomenal. I started seeing connections everywhere. Design systems aren’t just component libraries—they’re ecosystems. And AI agents could help us build intelligent tooling, documentation assistants, automated workflows, development aids that would multiply our team’s impact in ways I hadn’t even considered. More than that, I could see a path. A way to grow from UI engineering excellence into something broader without abandoning our foundation. A way to stay relevant—no, more than relevant, to stay essential—as the industry transforms around us. I came back from that learning journey energized. Maybe a little insufferable with excitement, if I’m being honest. The kind of energy where you want to grab everyone and say, “You have to see this!” So I did.
The Ask (Or: Please Trust Me On This)
I made it formal. Added it to our Q1 learning OKRs. Brought it to the team. “We’re all doing this course. Together. It’s going to take time. It’s going to be challenging. I’ve already done it, so I know what I’m asking. And I think—I genuinely think—this is where we need to go.” Here’s the humbling part: they said yes. They trusted me. These brilliant engineers who could have pushed back, who could have questioned whether this was the best use of their development time, who could have asked (rightfully) why the design system team needed to learn AI engineering… They trusted me. And if that doesn’t make you feel the weight of leadership, I don’t know what will.
The Journey (Together This Time)
Watching my team go through the same learning curve I did was… well, it was everything. Seeing them struggle with the same concepts I’d struggled with. Watching them have those “aha!” moments. Observing the shift from “I have to do this because it’s an OKR” to “Wait, this is actually really cool.” We shared insights. Helped each other through difficult sections. Celebrated wins. Commiserated over confusing documentation. Became better engineers together. And then, one by one, they finished.
The Transformation (Or: When Your Team Outgrows You)
Now my UI engineers are AI engineers too. They can build agentic systems in multiple frameworks. They understand MCP fundamentals. They’re designing intelligent automation for our ecosystem. They’re thinking bigger than components and patterns—they’re thinking about dynamic, intelligent systems that adapt and learn. But here’s the best part, the part that makes all those late nights worth it: They’re proposing ideas I haven’t thought of. They’re seeing applications I missed. They’re making connections I didn’t make. They’re pushing me to think differently. Which is exactly what you want, isn’t it? The moment when your team starts seeing further than you do? When the people you led become the ones showing you new paths? That’s not a failure of leadership. That’s the entire point.
The Messy Truth About Leading in Technology
I’m not going to stand here and pretend this was some masterfully executed strategic plan. It was messy. It was uncertain. There were moments where I genuinely wondered if I was leading us in the right direction or just following shiny objects because they were shiny. There were nights where I thought, “Maybe I should have waited. Maybe I should have studied this more. Maybe I’m being reckless with my team’s development.” But that’s the thing about being a technical leader in 2025: there is no playbook. The frontier doesn’t come with a map. You have to be willing to go out there, poke around in the dark, try things, fail at things, and figure out which paths make sense for your business. Then you have to come back and invite your team to explore with you. Not because you have all the answers. Because you’re willing to find them together.
What I’d Do Differently (The Honesty Section)
If I’m being completely transparent? I’d probably do the same thing again, but I’d worry less. I spent so much energy second-guessing myself. “Is this the right technology? Is this the right time? Am I being a good steward of my team’s development time?” And you know what? Those questions are important. They keep you honest. But they can also paralyze you if you let them. The truth is, you never have perfect information. You never feel completely ready. You just have to make the best decision you can with what you know, commit to it, and be willing to adjust if you’re wrong. Courage isn’t the absence of doubt. It’s moving forward despite it.
What’s Next (Because Standing Still Is Not an Option)
Now that we have these capabilities, the fun part begins. We’re exploring intelligent documentation systems that understand context. Automated accessibility testing agents. Design token management automation. Developer experience tools powered by AI. We’re also continuing to strengthen our core front-end engineering excellence—because this was never about abandoning our foundation. It was about building on it. Expanding it. Making sure we’re not just good at what we do today, but ready for what we’ll need to do tomorrow. The goal has always been evolution, not replacement. A team that’s as comfortable building AI agents as building React components. A team that can navigate uncertainty because they’ve done it before. A team that’s brave enough to grow.
For Leaders Who Are Wondering
If you’re thinking about upskilling your team in AI or any emerging technology, and you’re feeling that mix of excitement and terror that I felt, let me share what I’ve learned: Go first. Don’t just read about it. Build with it. Break things. Look foolish. Experience the learning curve yourself. You can’t lead somewhere you haven’t been. Validate before scaling. Make sure it’s actually worth your team’s time. Your enthusiasm is not sufficient evidence. The technology needs to connect to real problems and real value. Make it formal. Add it to OKRs. Create space for learning. Signal that this matters. People are busy—they need permission to prioritize learning over shipping. Learn together. Collective learning builds stronger teams than individual study. The insights you share, the struggles you commiserate over, the victories you celebrate—that’s how culture is built. Stay in the thick of it. Your team needs to see you learning alongside them. Not above them, directing from on high. With them, in the mess of it. Embrace the uncertainty. You will doubt yourself. You will wonder if you’re doing the right thing. That’s normal. That’s healthy. That’s leadership. Celebrate the moment when they outgrow you. Because that’s when you know you’ve done your job.
The Leadership Lesson Nobody Tells You
The best teams don’t follow leaders who have all the answers. They follow leaders who are brave enough to admit they don’t, humble enough to learn alongside them, and committed enough to find the answers together. The frontier is where the most interesting work happens. And it’s a lot less scary when you’re not exploring it alone. So here’s to late-night learning sessions. Here’s to looking foolish in pursuit of growth. Here’s to teams brave enough to follow leaders into the unknown. Here’s to the beautiful, messy, uncertain work of transformation. And here’s to coffee. So, so much coffee.
If you’re interested in the course that started this whole adventure: The Complete Agentic AI Engineering Course
Questions about leading technical teams through transformation? Want to commiserate about the challenges of upskilling? Think I’m completely wrong about something? I’m always up for a conversation. Reach out.
Now if you’ll excuse me, I have some AI agents to build. Turns out, learning never actually stops. (Who knew?) 😉