We were lucky to catch up with Ashley Mudd recently and have shared our conversation below.

Hi Ashley, thanks for joining us today. Can you tell us about an important lesson you learned while working at a prior job?

I still remember sitting across from my board chair at lunch, bracing for what I knew would be hard feedback. At the time, I was the Executive Director of a regional leadership development nonprofit—my dream job. I had set an arbitrary goal to become an executive director before I turned 30, and I hit it at 28. I thought I’d stay there forever.

I was proud of how hard I worked. I believed leadership was about grit, willpower, and proving myself. I worked constantly, always learning, always delivering more than was asked. But a few years in, I was exhausted. I felt unsupported, frustrated, and burned out.

That day over lunch, my board chair told me what no one else was willing to. The problem wasn’t that people weren’t supporting me—the problem was me. Every time I pitched a new idea, it was already 90% finished. I would then ask for input, but at that point, speaking up felt like pushing back against my work. My team didn’t feel like co-creators. They were just executing my vision.

It hit me hard. Here I was, leading a leadership development organization, and my way of leading was shutting people out. I thought I was carrying the weight for everyone, but in reality, I was keeping others from stepping in.

That conversation cracked something open in me. It was the beginning of realizing that leadership isn’t about doing the most or proving yourself. It’s about creating the container for others to contribute, to share ownership, and to lead alongside you.

That moment set me on a path to discover adaptive leadership, a framework that completely changed how I see my role and eventually inspired me to start my own company. It was the lesson that shifted everything I thought about leadership. Leadership isn’t about titles or grit, or even charisma. It’s about building the conditions for people to do good work, together.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

At the heart of my work is something simple: I like people. I love listening deeply, helping them navigate their passions and challenges, and seeing how their stories connect to something bigger.

That sense of interconnectedness started early. In high school, I took a course on the health of Louisiana’s coast and spent weekends planting marsh grasses to slow land loss. In college, I revisited that lesson, but this time it wasn’t just about the environment—it was about how poverty rates and educational outcomes tied directly into the same broken systems. Once I saw the connections, I couldn’t unsee them.

That insight drew me into nonprofit work. I worked across a variety of missions—youth development, literacy, economic empowerment—trying to tackle issues from different angles. But I struggled to go “all in” on a single cause, because everything was connected. That realization led me to an executive director role at a regional leadership development nonprofit, where I thought I had finally found my dream job.

It didn’t take long to realize I was burning out. I believed leadership meant grit, willpower, and proving myself. I over-delivered, carried too much, and eventually hit a wall. The turning point came when my board chair sat me down at lunch and gave me the difficult feedback. I wasn’t creating space for others.

That was hard to hear, but it cracked something open in me. Here I was, leading a leadership development organization, and my own way of leading was shutting people out. That conversation was the beginning of my journey into adaptive leadership, a framework that showed me leadership isn’t about titles or control—it’s about mobilizing others, creating the conditions for hard conversations, and sharing ownership of progress.

That realization eventually led me to start my own company. Today, my work falls into three main vehicles: coaching, facilitation, and leadership development. But what I’m really doing is working alongside leaders and teams to get clear on what success looks like on their terms, identify what’s within their control, and design processes where hard questions can be asked and difficult tensions can be raised without breaking trust.

Most people come to me at a crossroads—burned out, in conflict, or unsure what to do next. They can’t see a path forward. My role isn’t to hand them a blueprint. It’s to help them see reality clearly, identify the gap between where they are and where they want to be, and figure out what’s keeping that gap open. Then we work together to test new practices and make changes they’re actually willing to sustain.

What sets me apart isn’t a credential or a framework—it’s presence. I’ve had clients tell me the most valuable thing I gave them was remaining engaged and neutral while they shared something they were deeply ashamed of. I’ve had others appreciate that I don’t just tell them what they want to hear. My approach is deliberate and honest, grounded in the belief that how we do anything is how we do everything. The small shifts we make in one area ripple outward into bigger change.

I’m most proud of my clients’ progress—especially when they try new practices until they find what works for them. I’m also proud of the writing I do to share ideas more broadly. Writing doesn’t always change people overnight, but it can spark new perspectives—and sometimes a new perspective is all it takes to start moving forward.

What I want readers to know is this: leadership isn’t about doing the most or proving yourself. It’s about presence, practice, and the courage to invite others into the work. That’s what I help leaders and teams do—so they can not only make progress on their toughest challenges, but also build the capacity to keep doing it long after I’m gone.

Any thoughts, advice, or strategies you can share for fostering brand loyalty?

Someone once told me that what sets me apart is my ability to “operationalize empathy.” I’ve carried that with me ever since, because curiosity and empathy are at the core of who I am—not just in my personal life, but in how I run my business.

For me, staying connected with clients isn’t a marketing tactic, it’s a practice of empathy. I listen deeply, pay attention to the language that resonates with them, and try to meet them in the ways that feel most supportive. Sometimes that’s through a regular newsletter or a post on social media, other times it’s a virtual coffee or an in-person meetup. It’s less about the channel and more about the relationship.

I see this work as a balancing act. Yes, I run a business, and there’s always a pressure to “sell.” But coaching and strategic organizational design are deeply relational at their core. You can’t do this work without trust. So I prioritize the touchpoints that build genuine connection, even if they don’t immediately lead to a sale.

Part of that commitment is sharing what I’m learning—not just behind a paywall, but openly. I’m constantly working to deepen my own practice, and when I gain clarity on something, I want to translate it into actionable insights others can use. Whether or not someone ever becomes a client, my goal is that they walk away with something useful, something that sparks a new perspective.

That’s how I think about brand loyalty: not as a funnel, but as an ongoing relationship. If I can keep showing up with curiosity, empathy, and value, then people will know they can trust me to be in the work with them when they’re ready.

Can you talk to us about how your side-hustle turned into something more.

My first business transaction was actually an accident. In a volunteer role, I had created a curriculum on having cross-racial conversations. The organization I built it for saw the potential to profit from the curriculum and wanted to pay me for the intellectual property. I didn’t even know that was possible. We brought in lawyers, signed an agreement, and it all felt good—but in hindsight, I undersold myself. I undervalued my own work because I didn’t yet realize I had something of value to sell.

That mindset—learning to recognize the value of my ideas—has honestly been the hardest part of building a business.

During the pandemic, I was leading a regional leadership development organization where I facilitated in-person gatherings three times a week. Overnight, everything shifted online. I quickly adapted, translating my facilitation skills into virtual spaces. A local news station invited me to share tips with others learning to do the same. That moment was another reminder: I had value to offer. So when an organization approached me to subcontract their virtual facilitation, I said yes. It became my first ongoing contract, and I officially incorporated my business. From there, I facilitated team and board retreats, led strategic planning processes, and coached nonprofit executives.

The turning point came when an international nonprofit asked me to redesign one of their legacy programs—something I had done in my executive director role. They offered me a part-time position, which gave me the runway to leave my full-time job and grow my business beyond a side hustle. That was two years ago, and I’ve been building and refining ever since.

In the beginning, I branded myself as a nonprofit consultant. But over coffee with a friend who worked at a Fortune 100 company, I described my work. She told me they had just hired someone to do the same thing I was describing—at a significantly higher rate. That conversation was a wake-up call. I realized my work wasn’t limited to nonprofits. In fact, if I really wanted to create change, I couldn’t confine myself to just one sector.

So I rebranded as a leadership coach and facilitator. Today, I work with leaders and teams across industries who are ready to challenge the status quo and build systems where people can do good work. It’s not a path I planned from the start, but each step—each lesson in valuing my work—built the foundation for the business I run now.

Contact Info:

• Website: https://www.ashleymudd.com
• Instagram: https://www.instagram.com/ashley.mudd/
• Linkedin: https://www.linkedin.com/in/ashley-mudd/