Debra Clary
Founder & CEO
Louisville, KY
My Role
I work with senior leaders and executive teams to turn curiosity into a measurable performance advantage.
Most organizations think they have a performance problem. What they really have is a curiosity problem—people stop asking questions, stop challenging assumptions, and stop seeing what’s right in front of them. That’s where I come in.
Through keynotes, executive facilitation, and my Curiosity Curve® assessment, I help leaders see how curiosity is showing up—or getting shut down—across their organization. We identify where teams explore, engage, create, and stay open to new ideas, then translate those insights into practical shifts in leadership behavior, decision-making, and culture.
The result? Better conversations, sharper strategy, stronger trust, and teams that think instead of just execute.
In short: I help leaders stop solving the wrong problem and build cultures where growth, innovation, and performance can actually breathe.
What I love most about my role
What I love most is the moment leaders realize they’ve been solving the wrong problem.
I get to sit in rooms where smart, successful people are frustrated—by stalled growth, disengaged teams, or decisions that keep missing the mark. And then, almost quietly, curiosity enters the conversation. The energy shifts. Defensiveness drops. New questions surface. You can feel the room breathe again.
I love helping leaders see what’s been hiding in plain sight, patterns they couldn’t see because they were standing inside the frame. When curiosity shows up, people feel safer thinking out loud, telling the truth, and trying something new. That’s when real progress happens.
It’s deeply human work. It’s strategic. And it’s endlessly hopeful because the answers aren’t out there somewhere. They’re already in the room, waiting for the right questions.
How I define success
I define success as creating the conditions where people think better after you leave the room.
It’s not applause, titles, or perfectly executed plans. Success is when leaders ask braver questions, teams speak the truth sooner, and decisions get clearer because curiosity is alive—not performative.
It’s when progress feels sustainable instead of exhausting.
When people stop pretending they have the answers and start learning in real time.
When the work moves forward without burning everyone out.
If curiosity outlives my presence if people keep asking, listening, and challenging assumptions long after the session ends, that’s success.
Everything else is just noise.
The best piece of business advice I ever received was
“It’s difficult to see the picture when you’re in the frame.”
It changed how I lead, how I listen, and how I make decisions.
When you’re inside the frame, everything feels urgent, personal, emotional. Your perspective narrows. Curiosity shrinks. You defend instead of explore. Stepping outside the frame, slowing down, asking better questions, inviting other voices in, is where clarity lives.
That advice taught me that wisdom isn’t about having sharper answers. It’s about creating enough distance to see what’s really happening.
I still come back to it when things feel noisy or stuck.
Especially then.
What would I tell my younger self
ou don’t need to prove you belong by being the smartest person in the room.
Stop over-preparing. Stop carrying the weight alone. Ask the question you’re afraid will make you look inexperienced—it’s usually the one everyone else is thinking.
Trust your curiosity. It’s not a detour or a weakness; it’s the thing that will carry you further than confidence ever could.
And one more thing, rest isn’t a reward for getting everything right. It’s part of the work.
You’re not behind. You’re becoming.
What 2B Bolder mean to me
To be bolder isn’t about being louder or more certain.
It’s about being willing.
Willing to ask the question that hasn’t been approved yet.
Willing to pause instead of react.
Willing to tell the truth early, even when it’s inconvenient.
Boldness, to me, is choosing curiosity over comfort.
It’s stepping out of the frame so you can see the whole picture and then having the courage to act on what you see. Not perfectly. Not noisily. Just honestly.
That kind of boldness changes conversations.
And conversations change everything.
Years of Experience
40
I recommend you focus on developing these 3 skills to succeed in a role like mine
1. Seeing patterns others miss
I can walk into complex organizations and quickly spot what’s actually driving behavior—where curiosity is thriving, where it’s getting shut down, and why performance is stalling beneath the surface.
2. Asking questions that unlock better thinking
Not the polite, performative kind. The kind that slow people down, surface truth, and move conversations from defensiveness to discovery.
3. Translating insight into action
I don’t leave leaders inspired and stranded. I help turn awareness into practical shifts in how teams lead, decide, and work together—so change sticks after the meeting ends.