Early Life: Foundations of Leadership

"Witnessing my father's compassion in the hospital taught me lessons no textbook ever could."

Tim: Let’s go back to the beginning. What's your story?

Kaitlyn: I grew up in a tight-knit Midwestern community in Ohio—where Friday nights meant neighborhood block parties, weekends were for back-to-back soccer games, and summer days ended with laughter echoing from the pool to the cul-de-sac. It was the kind of childhood where you felt known, safe, and wildly free.

At the heart of it all were my parents—high school sweethearts who built a home anchored in love, structure, and deep values. My dad was the definition of grit and grace. A respected medical professional, but to me, he was more than his title. He was the man who’d let me tag along to hospital rounds, who treated every patient—no matter how sick—with unwavering presence and care. Watching him calm someone in pain with nothing more than his voice and a hand on their shoulder showed me that leadership doesn’t need to be loud to be powerful.

My mom was the emotional center of our home. She made people feel safe just by being in the room. As a tutor and school psychologist, she had this incredible ability to meet kids exactly where they were and help them rise without shame. She saw potential in everyone—including me, especially during the seasons I couldn’t quite see it myself. Her calm, her belief in me, and her quiet strength have been the blueprint for how I support others now.

Then there’s my older brother—two and a half years wiser, my protector in a hands-off kind of way. He never hovered, but he was always there. Letting me figure things out, supporting me when I soared and when I stumbled. He’s one of the kindest, most brilliant humans I know, and I’ve looked up to him my whole life.

But it wasn’t all easy. School, in particular, was a struggle—largely due to undiagnosed ADHD. While my social world thrived (I’ve always been fueled by connection), the academic side of things felt like a constant uphill climb. I worked hard, harder than most, just to stay afloat. But those challenges became the soil where my resilience grew. They taught me how to find joy even in struggle, and how to build confidence outside of performance.

Looking back, I wouldn’t change any of it. Because every piece—my family, my challenges, my Midwestern roots—shaped the coach I am today. Someone who leads with heart, sees the whole human, and believes deeply in every person’s ability to grow into who they’re here to be.

Here I am with the protector, my brother, Matthew, as a kid. Not only a brother, but a best friend.

Facing Challenges Head-On

"Discovering I had ADHD wasn't a setback—it became my greatest strength."

Tim: How did ADHD affect your school years?

Kaitlyn: School was never easy for me—especially in environments where success was defined by how quietly and quickly you could follow the rules. While my peers seemed to move through assignments and tests with ease, I was often stuck behind the scenes—mentally sprinting to keep up. Paying attention felt like trying to grab fog. Organizing homework? Overwhelming. Standardized tests? Nearly impossible. But the one thing I never lacked was grit. I may have struggled in silence, but I refused to give up.

My mom—who had been a school psychologist before I was born—was my anchor. She never saw me as “difficult” or “disorganized.” She saw me as capable, just wired differently. Her belief in me helped me believe in myself, even when I felt behind. She gave me structure, grace, and a deep understanding of how to self-advocate—skills I still use every single day.

It wasn’t until college, when I hit a wall of academic exhaustion, that I finally pursued testing and was diagnosed with ADHD. That moment was life-changing—not because it gave me an excuse, but because it gave me context. Suddenly, everything made sense. I wasn’t lazy. I wasn’t less than. I was navigating a brain that processed the world differently—and that realization changed everything.

With that self-awareness, I started advocating for myself. I met with professors face-to-face, asked for visual aids ahead of lectures, requested extra time on exams—not from a place of shame, but from ownership. And the shift was immediate. I went from feeling invisible to being fully engaged. From frustrated to focused.

ADHD didn’t just challenge me—it shaped me. It taught me how to work twice as hard, listen more closely, and create systems that support real success. And now, as a coach, it allows me to see and support other high performers who are walking that same road—people who are brilliant, but just need to build their life around how they actually work.

Here I am with my mom enjoying the Opryland Lights in Tennessee last December.

Here I am with my dad enjoying a night in while grilling on the porch.

Early Career Insights

"Answering calls during the financial crisis taught me the art of listening in ways I'd never imagined."

Tim: Tell us about your early career experiences.

Kaitlyn: My career began in the deep end—on the phones as a client service representative during the 2008 financial crisis. Every call was emotionally charged—people were panicked, frustrated, and heartbroken watching their savings vanish. I was 22, and suddenly the person on the other end of the line holding space for their fear. That role taught me empathy in real time. It taught me to listen beyond words, regulate emotion in high-stress situations, and remain steady when others were spiraling. That experience shaped the emotional intelligence I bring into coaching today.

From there, I pivoted into venture capital—first as a receptionist and eventually managing high-level external events for partners and founders. It wasn’t just a job; it was an accelerated course in executive communication, stakeholder management, and presence. I made it my mission to treat every person—from first-time founders to tenured investors—with warmth and clarity. Relationships were everything. That’s also where I met one of my earliest mentors, David, who saw something in me before I fully saw it in myself. He taught me to anticipate problems before they surfaced, to lead through curiosity, and to view every challenge as a chance to innovate. That mentorship remains one of the greatest gifts of my professional life.

Eventually, I was recruited into a portfolio company and rose to Chief of Staff. That role was a defining chapter. I operated at the intersection of leadership alignment, operational efficiency, and executive decision-making. I facilitated strategic planning, built accountability systems, ran cross-functional initiatives, and became a trusted partner to the CEO. It was the seat where I learned to manage both people and pressure—how to read a room, steer tough conversations, and build trust through both words and presence.

Each of those roles—client service, venture capital, executive operations—gave me tools I still use today. But more importantly, they showed me who I was becoming: someone who could lead with both heart and precision. That realization was the turning point that eventually led me to coaching.

The Power of Coaching

"I don’t just coach to improve performance. I coach to help leaders come home to themselves."

Tim: When did you realize coaching was your calling?

Kaitlyn: I’ve always felt this innate pull to step in, support, and lift others up. I knew early on that I thrived when I was in service to others.

But the realization that coaching was my calling didn’t hit me all at once. It was more like a series of internal whispers that became too loud to ignore. In my corporate career—especially in high-intensity leadership roles like Chief of Staff—I was the calm in the chaos. I was the fixer, the intuitive one, the person leaders turned to when they couldn’t see a way forward. And yet, I began to notice that something was missing. I was helping systems run smoother, helping people hit goals—but I wasn’t seeing the kind of personal transformation that I knew was possible.

Eventually, I realized my deepest fulfillment didn’t come from scaling operations or hosting high-stakes events—it came from the moments in between. The hallway conversations, the late-night calls, the real, vulnerable breakthroughs. I was most alive when I was holding space for someone’s clarity to emerge. And I realized I didn’t want to just support leaders behind the scenes—I wanted to walk beside them as their thought partner, their guide, their mirror.

Coaching became the obvious answer to a question I’d unknowingly been asking my whole life: How do I help people step into their full, aligned potential—without burning out or losing themselves in the process?

Now, I coach visionary CEOs and high-level leaders who are under immense pressure to perform. These are people who carry the weight of hundreds, sometimes thousands, of lives and livelihoods. But they’re also human. They crave space to think clearly, to reconnect with themselves, and to lead with more heart and less noise. That’s what I help them do.

I believe I was born with a unique blend of strategic thinking, intuition, and deep care—and coaching allows me to bring all of those gifts to the table. I don’t just coach to improve performance. I coach to help leaders come home to themselves. When they do, they create ripple effects that transform their teams, their companies, and often their lives.

Kaitlyn’s Unique Coaching Style

“The best coaching doesn’t sound like commands—it feels like clarity.”

Tim: Many perceive coaches as people who tell you what to do, but you prefer a different approach. Why?

Kaitlyn: I truly believe the best coaching doesn’t sound like commands—it feels like clarity. It’s not about giving advice from a pedestal, it’s about walking beside someone and helping them access the clarity, confidence, and capacity that’s already inside them.

When people hear “coach,” they often picture someone with issuing directives. But leadership isn’t a checklist—it’s deeply personal. Every CEO I work with is navigating a unique mix of complexity: high-stakes decisions, internal doubt, external pressure, and the unrelenting expectation to have it all together. My approach is to create a safe, confidential space where we cut through the noise, get honest, and start unlocking what’s true for them—not what worked for someone else.

My job isn’t to prescribe answers. It’s to ask the questions no one else is asking, to listen for what’s not being said, and to reflect back patterns they can’t yet see. I act as a strategic thought partner, an intuition amplifier, and a mirror for their most aligned leadership. Together, we co-create solutions that not only work—but feel right. Because when decisions are made from internal alignment, they become sustainable and impactful.

So no, I don’t tell clients what to do. I guide them back to their own wisdom, sharpen their vision, and help them lead with more conviction and less noise. Because aligned leaders build aligned companies—and that ripple effect is what I’m here for.

ADHD: Superpower or Setback?

“My brain doesn’t stay in a box—so I help my clients break out of theirs.”

Tim: Many CEOs struggle with ADHD. Has it been a blessing or a challenge for you?

Kaitlyn: Both—and I wouldn’t change a thing about it.

ADHD used to feel like my biggest hurdle. In school, I remember wishing I could read faster, focus longer, or organize my thoughts like everyone else seemed to. I was working twice as hard just to keep up—and often still felt behind. It wasn't until college, when I finally received a diagnosis and began to understand how my brain worked, that things started to shift. That awareness changed everything.

What once felt like chaos has now become one of my greatest assets. ADHD has taught me how to think differently, and in the business world—especially at the CEO level—that’s gold. It’s given me creativity that cuts through complexity, intuition that picks up on what others miss, and a natural ability to connect seemingly unrelated ideas in innovative ways. My mind doesn’t stay in a box—so I help my clients break out of theirs.

That said, success didn’t happen by accident. I had to build systems to support my flow. I created rituals, frameworks, and rhythms that channel my energy instead of trying to suppress it. ADHD forced me to master prioritization, time blocking, and boundaries—not just for productivity, but for peace of mind. And now, I pass those tools on to the CEOs I coach, many of whom are just beginning to realize that their “distraction” might actually be misunderstood brilliance.

I meet so many leaders who secretly carry shame around their ADHD. They think it means they’re broken or inconsistent. But here’s what I tell them: You’re not too much. You’re not scattered. You’re wired for a different kind of greatness. And once we align your systems to your strengths, that’s when everything clicks.

So yes—ADHD has been a challenge. But more than that, it’s been a gift. It’s helped me lead with more empathy, coach with more insight, and create transformations that honor how people actually work. And that’s not just transformative—it’s liberating.

Connecting Deeply with Clients

“I’m not a passive observer in my clients’ journey—I’m a partner in their evolution.”

Tim: You work closely with influential CEOs. How do you maintain such meaningful relationships?

Kaitlyn: It starts with one core belief: behind every powerful title is a human being who’s carrying an extraordinary amount of pressure, responsibility, and often, silent self-doubt. I don’t coach titles—I coach people. And that’s why the relationships I build with my clients are so meaningful.

My practice is built on trust, discretion, and emotional presence. These leaders are used to being the ones with all the answers. Rarely do they have a space where they can say, “I don’t know,” or “I’m struggling,” without fear of judgment or consequence. I create that space—and I protect it fiercely. When someone feels fully seen and not managed, when they’re heard without agenda, that's when the real relationship begins.

Coaching at this level involves more than frameworks and KPIs—it requires deep listening, intuitive insight, and shared investment. I’m not a passive observer in my clients' journey. I care deeply about their growth, their clarity, and their wellbeing. When they win, I celebrate with them. When they stumble, I’m right there helping them reset—not from a place of fixing, but from a place of aligned support.

And I don’t just show up for their leadership—I show up for them. Their vision. Their families. Their legacy. I’ve had clients text me before board meetings, after major decisions, or in quiet moments of doubt. They know I’m in their corner—not just as a coach, but as a trusted partner.

That level of connection doesn't just happen—it’s cultivated. It’s why I only take on a select number of clients. Because this isn’t surface-level work—it’s transformational, relational, and long-term. And when it’s done right, the relationship becomes a foundation they can build from—personally and professionally.

Micro Shifts, Massive Results

“A 1% shift in a CEO doesn’t stay small—it echoes through an entire company.”

Tim: I’m curious, Kaitlyn—how does it feel to have that much impact? I mean, when you coach a CEO or a president of a company, someone whose decisions affect hundreds or even thousands of people... the leverage of even a small mindset shift can be massive. A 2% improvement in their thinking could create ripple effects worth tens of millions of dollars. Does that ever make you nervous?

Kaitlyn: Honestly? It doesn’t make me nervous—it fuels me. That’s what excites me about this work.

Because it’s true—when one leader evolves, the ripple is exponential. A single shift in mindset, a moment of clarity, a deeper connection to purpose—it cascades through their team, their culture, their business, and even their home life. That’s the kind of leverage I live for.

But I never forget that behind the title, behind the P&L statements and strategy decks, is a human. Just a person. And when we remember that—when we start with the person—we unlock a completely different level of impact.

I always say: if we can help someone grow by just 1%, imagine what happens when that 1% multiplies across hundreds of employees, thousands of decisions, and years of leadership. That’s not just business evolution—that’s legacy work.

So no, it doesn’t make me nervous. It makes me present. Grateful. And deeply committed to holding the kind of space that allows real change to happen. Because at the end of the day, humans will human—and if I can help one of them do it with more clarity, care, and conviction, then I know I’ve done meaningful work.

The Thinking Edge: What AI Can’t Replace

“AI can generate answers. But it’s your thinking, empathy, and communication that drive alignment, trust, and momentum. That’s leadership—and that’s still human.”

Tim: We’re living in a time where AI is rapidly becoming a dominant force. One thing I heard recently that really stuck with me is, “Knowledge is a commodity. Thinking is power.” That shift in mindset—that being able to think clearly and lead with emotional intelligence—has a bigger ripple effect than most of the traditional levers we pull as CEOs. What’s your take on that?

Kaitlyn: I love this conversation because it hits on something I see every day inside executive coaching: knowledge is now limitless. AI can pull data, summarize white papers, draft strategies, even analyze performance metrics faster than any human could. So yes—knowledge is a commodity. But the real differentiator? How we think, how we discern, and how we communicate.

That’s where leadership still belongs to humans. CEOs don’t win because they know more—they win because they know how to pause, interpret, decide, and communicate in a way that moves people and aligns vision. You can’t outsource emotional intelligence. You can’t automate self-awareness. You can’t replicate empathy through a chatbot.

And that’s where I come in. My work isn’t about adding more noise or data points—it’s about helping leaders clarify their thinking and then communicate it effectively. Because it’s one thing to have access to information. It’s another thing entirely to know how to translate that into action that earns trust, builds alignment, and moves a company forward.

The CEOs I work with already have the knowledge—they’re swimming in it. But they come to me when they need to lead with clarity, consistency, and presence. And in a world where everyone has access to the same information, the way you show up, the way you think, and the way you make people feel is what sets you apart.

Kaitlyn’s Vision: Breaking Isolation

“The pressure won’t disappear—but how you hold it can change everything.”

Tim: What’s your message to a CEO who feels alone under immense pressure?

Kaitlyn: You may be surrounded by people, but I know how leadership can still feel lonely—especially at the top. You're carrying the weight of decisions that impact teams, revenue, families, and futures… and yet, there’s often no one safe to say, “I’m not okay.”

So here’s what I want you to know: You are not alone. Not in your doubt, your overwhelm, your sleepless nights, or your silent second-guessing. What you’re feeling is real—and you don’t have to keep white-knuckling your way through it.

Taking that first step to seek support isn’t weakness—it’s wisdom. It’s the kind of self-awareness and courage that sets great leaders apart. Because no one climbs sustainably without support. And the strongest CEOs I know? They’re not afraid to ask for help. They invest in thought partners, sounding boards, and spaces where they don’t have to have it all figured out.

I’ve seen time and time again: when leaders finally exhale, admit they’re at capacity, and give themselves permission to be human—the transformation is immediate. Relief enters the room. Clarity sharpens. Energy comes back. And leadership becomes something you own, not something that owns you.

So if you’re that CEO silently holding it all in: You don’t need to carry this alone. You're allowed to receive. You're allowed to reset. And yes—you can still lead at the highest level and feel supported, fulfilled, and mentally well while doing it.

The pressure doesn’t go away. But how you hold it? That can change everything.

The Real Enemy: Complacency and Pride

“Businesses grow at the pace their leaders do.”

Tim: You know, Kaitlyn, in my own career, I’ve always made it a priority to have coaches, to be in mastermind groups, and to surround myself with people who are moving in the same direction—people who’ve done things I aspire to do. And honestly, when I look at the high-performing CEOs I know and respect, almost all of them have a coach.

Yet, most CEOs still don’t. Some see coaching as something they don’t need—or something reserved for a crisis. But then I think… did Michael Jordan have a coach? Of course he did. He was one of the greatest of all time, and he still relied on guidance to get better.

So with that in mind, I want to ask you this: In your world—working with some of the most successful leaders in business—what or who is the enemy? 

Kaitlyn: The enemy? Pride masquerading as strength. Complacency dressed up as certainty.

What concerns me most isn’t failure—it’s stagnation. It’s the leader who stops listening. Who stops learning. Who believes they’ve arrived. Because the moment you think there’s nothing left to grow, you’ve already started declining—personally, culturally, and often, financially.

I’ve seen how unchecked pride isolates leaders. It creates blind spots, erodes trust, and quietly infects an organization from the inside out. Teams stop speaking up. Innovation stalls. Alignment fractures. And all of it stems from one belief: “I don’t need help.”

But true leadership doesn’t pretend to have all the answers. It has the courage to ask better questions. It’s rooted in humility—the kind that says, “I’ve come far, but I know I can go further.” The CEOs I work with aren’t weak for seeking support—they’re wise. They’ve traded the illusion of perfection for the power of perspective.

So if there’s an enemy in my practice, it’s the mindset that resists growth. That clings to control instead of inviting collaboration. That settles for “good enough” when greatness is still on the table. My role is to challenge that stagnation—to help leaders evolve, not just operate. Because businesses grow at the pace their leaders do. And when a leader chooses expansion over ego, everyone around them rises, too.

The Foundation I Stand On

“Intuition opens the door. Grit gets you through it. Mindset keeps you moving forward.”

Tim: Let’s shift gears for a moment. What are the top three things you’re most proud of in yourself?

Kaitlyn: That’s such a great question—and, if I’m being honest, one that’s harder for me than it sounds. I’m so naturally attuned to seeing greatness in others. It’s what I do—spotting the brilliance that people don’t always see in themselves. But turning that lens inward? That’s a growth edge I’ve had to embrace over time.

That said, there are three qualities I’ve come to deeply honor in myself:

First, my intuition. It’s more than just a gut feeling—it’s an internal compass that helps me read the room, sense unspoken needs, and create a space where people feel immediately safe, seen, and heard. That trust people feel with me? It starts with that intuition. It’s not something I’ve forced—it’s something I’ve nurtured.

Second, my grit. I don’t give up. Whether it’s been academic struggles, career pivots, or launching a business from scratch, I’ve learned how to show up—even when the path isn’t clear. That determination has carried me through some of the hardest and most defining moments of my life.

And third, my mindset. It’s been built through challenge. It’s the belief that growth is always possible, that I can hold discomfort and still lead, and that I get to define success on my own terms. That mindset is the foundation I coach from—but it’s also what allows me to live what I teach.

All three—intuition, grit, and mindset—are the thread that runs through my work, my life, and the way I support others. I’m proud of them not just because they’ve helped me get where I am, but because they’ve allowed me to do it without losing who I am along the way.

Here I am with the whole family! Mom, dad, brother, Matthew, sister-in-law, Jenn, niece, Julia, my Uncle Greg and dog, Briley.

Tim: Thank you, Kaitlyn. That was an amazing interview. Thanks for being so open and vulnerable. More than anything, I just want to say thank you—for the impact you’ve had on my life, and on the lives of my 700+ employees. I’m a better leader, and a better human, because of our work together.

Kaitlyn: Thank you, Tim. It means the world to be in spaces where depth, truth, and leadership can coexist. I’m grateful for the conversation—and even more grateful for the work we both get to do in service of something bigger. Total joy. Let’s keep going.

On the mic as a guest speaker for an upcoming podcast.