Changemaker Series: J.B. Skelton

Welcome to Changemaker Stories from LOCAL - an ongoing series of personal interviews with leaders driving change across every industry and discipline. Because change shouldn’t mean going it alone.

‍This week, we caught up with J.B. Skelton, a lifelong storyteller and seasoned communicator whose career has spanned top-tier tech giants like Meta and Microsoft. We talked about the power of curiosity, the magic of experimenting with new tools, and the clarity he’s found on the shores of a quiet lake in Guatemala.

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I think everyone experiences different seasons in their career. You start as a total beginner, figuring out what excellence looks like and how to deliver it consistently. Then you learn how to truly delight a customer—and eventually, how to do that at scale. Over time, you take on more responsibility, learning how to manage projects, lead teams, and bring others along on the journey.

In past roles, I was leading large teams—dozens of people—and now I’m back in an individual contributor role. Honestly, it’s been really freeing. I’ve seen others go through the same shift, and it can be tough to let go of that identity. There’s this quiet question that creeps in: Who am I without the big team? But for me, it’s been a chance to reconnect with the work I love and to redefine what impact looks like.

I’m a big people person. I love connecting with others—and connecting people to each other. I’ve had to find new ways to do that, even when it’s no longer built into the role. It’s pushed me to be more intentional about how I build relationships, and reminded me that leadership isn’t always about your title.

That’s actually one of the reasons I started my podcast. I love making introductions—it’s one of my favorite things to do. My friend Molly is the same way, so we created a show around that instinct. In each episode, she introduces a friend to me, I introduce a friend to her, and we dive into open-ended conversations about work, leadership, and life that have a lot of laughter. We think work should be fun—even joyful

When you’re working in creativity, communications, and leadership, change is the one constant. It’s always there—shaping the world around us, shifting markets, evolving customer needs. But it’s not just external. Some of the biggest shifts happen within ourselves. The real work is learning how to adapt—again and again—and staying open to what that change is asking of us.

One practice I’ve found really helpful outside of work is trying something new a couple of times a year. Last summer, I picked up watercolors for the first time. I’ve worked with oils before, where you can cover up mistakes and make changes as you go. But with watercolors, once the paint hits the paper, it’s there for good. 

I also like to push myself physically by trying new things. A couple years ago, I started doing Pilates—teaching my body to move in ways it never had before. Over time, I found my rhythm, started feeling strong, and thought, Okay, I’ve got this. Which, of course, meant it was time to shake things up again. So three weeks ago, I started Barry’s... and I’m an absolute mess.

I think it’s so important to keep pushing yourself into a beginner’s mindset. People throw that phrase around a lot, but it really matters. There’s something humbling and powerful about retraining your muscles—whether physical, mental, or creative—to work in new ways. 

The more time I spend in that beginner’s mindset, the more comfortable I get with making a fool of myself. Whether I’m trying out AI tools at work or learning something totally new, I know I’m not going to get it right on the first try—and that’s okay. I’m probably going to fall on my face a few times. But leaning into that discomfort helps you get over the fear of failure really quickly.

I take the same approach with podcasting. When we started, we were terrible. We had to learn how to land an interview and how to take an audience on a narrative journey in just 35 or 45 minutes. The more I embrace that beginner’s mindset, the more I see it show up in my work

I spent 12 years at Meta, and one thing the company does really well is instilling that beginner’s mindset. They encourage trying a ton of things, knowing that some of them will fail. But at the end of every project, you walk away with a deeper understanding of what to repeat and what to avoid.

‍People may not remember this, but we launched a phone at Facebook. To put it delicately, it was decidedly NOT a success. But even in that failure, there were elements of the interface that ended up living on in later products.

The phone itself was a flop, but some of the design and UI features really pushed the boundaries of how people connected and had conversations over the phone. Elements from that interface were eventually integrated into Messenger, WhatsApp, and several other products we still use today.

Out of what was ostensibly our biggest product failure to date, there were real successes. That phone launch didn’t go the way we hoped, but looking back, it’s clear that the lessons and innovations from that failure lived on in different ways. 

“It's okay to fail.”

If you're not expecting to fail at some of your goals, you're probably not aiming high enough. At Meta, we used to set ambitious top-line company goals and only expected to hit about half of them.

I remember sitting in an audience back in 2017 when our Chief Revenue Officer told us that by 2021, we’d have a $100 billion business. At the time, we were at $40 billion, and it seemed almost unreachable. But we didn’t just meet that goal—we beat it by 20%, which was incredible. 

When I first joined, there were about 1,500 people at Meta. By the time I left, the company had grown to 85,000 full-time employees, with another 60,000 contractors—around 150,000 people in total. Watching the team grow by 100x was an extraordinary experience, but it also meant the culture changed massively.

I think one of Meta’s biggest superpowers was its ability to go back into the cocoon every few years and emerge as an entirely different company. It started as a desktop-only platform, then transformed into a mobile-first company, and it continues to evolve in new ways today. 

I think semiannual employee surveys are incredibly important. They provide a deep understanding of your employees' mindset, which is invaluable for shaping a healthy, productive culture. Feedback needs to be as honest and granular as possible so that it reaches down to the manager level. 

With that granular feedback, managers can ask themselves critical questions: Is my team happy? Do they believe in me? Am I giving them the right information? Am I filling their cups? Am I inspiring them? And importantly, Am I arming them with the tools they need to succeed every day?

I think a lot of companies don’t take the time to do these types of surveys, and if they do, they often don’t dive deep enough into the manager-level granularity. Without that level of detail, feedback becomes too general to be actionable.

‍Whether you're a CEO or just starting out in your career, I think everyone should curiously explore all of the tools available. Get a paid subscription to ChatGPT, Claude, Sora—whatever you can—and start playing with them. Understand what they do, how you can use them, and most importantly, develop your own perspective on them.

It’s actually really fun, too. One of my favorite things to do is write plot summaries for Hallmark movies using the top people in your chat thread, and then email the plot summary to those folks. It’s a silly way to goof around with the tool and see what it can do, but it’s also a reminder that the best way to learn is to just experiment, have fun, and see where the tools take you.

Be curious about the world in general. I make it a point to read widely, go to the theater, and listen to live music. These experiences provide me with new perspectives and ideas that directly inform how I approach my work. 

Writing is thinking. As you gather all of these inputs, keeping a journal is a great way to organize your thoughts. Journaling accelerates your ability to develop perspectives quickly. It’s like exercise for the mind. 

One of the places that inspires me most is Lake Atitlan in Guatemala. I try to go every year. It’s a caldera high up in the Guatemalan highlands, and no one knows how deep the lake is. There’s this quiet, off-the-grid hotel on the north side of the lake that feels like summer camp. It’s only accessible by boat—there are no roads. You’re completely removed from the world, and that’s why I love it. I go there to think, swim, read, and reset. 

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