I grew up in the South Bronx in an apartment full of music, laughter, and life. My father was the center of it—parties, dancing, people everywhere.

Then one day, he was gone. No goodbye. No explanation. Just silence.

That's where I first learned to figure things out on my own. To not need anyone. To perform "okay" even when I wasn't.

I also learned early that I didn't quite fit anywhere. Not "Black enough" for some rooms. Not "white enough" for others. Never quite belonging. So I made belonging my project—learning to read every room, adjust to every situation, earn my place instead of assuming I had one.

If you've ever walked into a room where you technically belong but still feel like an outsider—I know that experience from the inside out.

"Deborah Get's it!"

Many see bridges as a place to watch the swirling water below or feel the wind.

Looking over the edge but not ahead, then returning to where they began.

But bridges aren’t meant for retreat.They’re meant for crossing.

And I help you cross.

About Deborah Guy
 

Certified Executive Coach

Deborah Guy is a certified executive coach and fear mastery specialist who helps leaders overcome imposter syndrome, self-sabotage, and the invisible patterns that keep capable people playing smaller than their potential. With 25+ years of experience—including directing executive coaching programs for Fortune 100 companies—she brings both corporate credibility and deep personal understanding to her work with leaders navigating high-stakes transitions.

Most of us spend our careers trying to manage around fear instead of moving through it. We overthink to avoid making the wrong decision. We overwork to prove we belong. We avoid difficult conversations because we might not handle them perfectly.

But here's what I've discovered: Fear isn't the enemy of good leadership. Fear that's driving your decisions unconsciously - that's the problem.

When you learn to recognize fear-based patterns and make conscious choices about how to respond to them, everything shifts. Your confidence stops depending on everything going perfectly. Your influence grows because you're not managing your own anxiety in every interaction. You make decisions faster because you trust your judgment.

As a certified fear mastery coach, I don't help you eliminate fear—that's impossible. I help you develop the internal resources to move through it, again and again.

This is what I call Grounded Leadership™—helping you move through fear, not away from it. Because every leadership breakthrough requires stepping into territory that feels uncertain, and the leaders who thrive are the ones who've learned to trust themselves in that space.

Because every leadership breakthrough requires stepping into territory that feels uncertain, and the leaders who thrive are the ones who've learned to trust themselves in that space.


What I've learned about fear (and why it matters for your leadership).

I don't hand you personality assessments to explain why you are the way you are. I don't give you a system to follow or ask you to journal about your childhood.

Instead, we focus on what's happening right now. What patterns are keeping you stuck? What would change if you trusted your instincts as much as your analysis? What becomes possible when you stop managing fear and start leading through it?

My approach blends fear mastery coaching, practical behavioral change techniques, and the kind of real-time problem-solving that actually works in your world. But honestly, the frameworks matter less than what actually happens: You start seeing your patterns clearly. You build the courage to make different choices. You develop the internal foundation that supports whatever you're trying to create.

Clients describe the work as both grounding and catalytic. Conversations that feel immediately helpful and transformative over time.

I witness the leader and the life you say you want—and hold you accountable for achieving it.

We work together either one-on-one in strategic intervention coaching or in the Grounded Leadership™ Group, where professionals build emotional leadership skills in a community setting.


What actually happens when we work together

There's a moment when you stop blaming circumstances and start telling the truth.

Mine sounded like this: "My way isn't working."

Not "I had bad luck." Not "They didn't understand me." Just the simple, devastating fact that the way I'd been living had led me exactly here.

So I made a choice. No more drinking. No more dishonest shortcuts. No more pretending everything was fine. I rebuilt from the ground up.

And then something unexpected happened. I got hired at TIAA-CREF and kept getting promoted. I was in rooms I never imagined I'd be in—working with the president, the chairman, the board.

I noticed something surprising: the executives were just as scared as I had been. The guy chairing a multimillion-dollar board meeting? Terrified of a conversation with his own daughter. The woman leading a national initiative? Convinced she'd be "found out" any day.

Their titles were impressive. Their fear was identical to mine.

Around that same time, I started volunteering at Streetwork—a program for homeless and runaway youth in Times Square.

I watched teenagers choose the street over safety, chaos over help. At first I didn't understand. Then it clicked: they weren't being irrational. They were terrified. The street was painful, but it was what they could control.

And suddenly I saw it everywhere—in them, in the executives, in myself:

Fear, when unexamined, drives our decisions. It doesn't care about your title or your tax bracket. It just runs the show until you learn how to work with it.

That insight changed everything. Within a few years, I was handpicked by the Chairman of a Fortune 100 company to direct their executive coaching programs—not because I had all the answers, but because I'd learned to navigate uncertainty without letting fear run the show.

And that's when everything changed. 

By my twenties, I'd made it to Wall Street. Mitsui. EF Hutton, Prudential.  An apartment in the Village. Money in my pocket for the first time in my life.

On paper, I was winning. I was smart, likeable, full of potential. I earned recognition, got promoted, built the kind of resume that opens doors.

But underneath? I was scared. I knew I'd received my opportunities based on ability, likability, and a willingness to be of service. But I was surrounded by MBAs and pedigrees. I had neither in a place that coveted both. I'd adopted a fake-it-til-you-make-it approach—and every opportunity felt like it brought me closer to the precipice of being "found out."

I began to self-sabotage opportunities for promotion, afraid that this time—this time—they'd figure out there was stuff they thought I could do that I didn't actually know how to do. Asking for help, exposing that, felt out of the question.

And not asking for help is what finally did me in.

Standing in the wreckage of that, I finally saw clearly: I wasn't ever incompetent. I was afraid.



Here's how I learned what actually matters

Grounded Leadership™ is Deborah's signature methodology that helps leaders master their relationship with fear. Rather than trying to eliminate fear (which is impossible), this approach teaches leaders to recognize fear-based patterns—imposter syndrome, perfectionism, avoidance, people-pleasing—and develop the internal capacity to move through them. The result is confident, decisive leadership grounded in self-trust rather than anxiety management.

I've coached leaders from Denver to Dubai, working with executives navigating transitions across industries and continents.  For several years I was Director of TIAA's national mentoring initiative  I directed mentoring initiatives nationally, funded by the President and later the Chairman of TIAA, creating connections between senior executives, and up and coming professionals. 
But honestly? The work I'm most proud of happens outside of the office.

My husband of nearly 35 years and I were both born and raised in NYC and started our family there, later moving to the Hudson Valley where our family of three daughters grew and thrived. A few years ago we moved to Annapolis outside of DC, an area we now call home.

This work isn't separate from that life—it's an extension of it. The same principles that create thriving leadership create thriving relationships. Both require the courage to show up as who you really are.

At 38, I made the scariest decision of my life: I walked away from a career that looked successful to build a life that actually felt like mine. Not because I had it all figured out—but because I finally trusted myself more than I trusted my fear.

I got certified in Fear Mastery—two and a half years of real, difficult, transformative work. And instead of going back to a "safe" corporate job, I chose to help people do what I had learned to do: stop managing around their patterns and start living from their actual power.

Because the best coaching isn't about fixing who you are—it's about freeing who you've always been when you're at your best.

The work that matters most.

Frequently Asked Questions

About Working With Deborah

What are Deborah's coaching credentials?

Deborah is a certified executive coach and certified fear mastery coach with 25+ years of experience. She was handpicked by the Chairman of a Fortune 100 company to direct their executive coaching program. Her background includes a decade in IT leadership at TIAA and Prudential, plus 40+ years of nonprofit leadership experience including serving as United Way co-chair at TIAA. She has coached leaders across industries from technology to nonprofit, from Denver to Dubai.

What makes Deborah different from other executive coaches?

Deborah specializes in fear mastery—the invisible patterns (imposter syndrome, perfectionism, self-sabotage) that keep capable leaders stuck. Rather than surface-level tactics, her Grounded Leadership™ approach addresses the root causes of self-doubt and hesitation. She brings both corporate executive experience and deep personal understanding of what it takes to lead authentically. Her approach blends high-trust human connection with practical tools you can apply immediately.

What industries or roles does Deborah work with?

Deborah works primarily with IT and fintech leaders navigating AI disruption and expanded responsibility, nonprofit executives balancing mission with sustainability, and emerging leaders preparing for promotion or adjusting to new roles. Her methodology applies across industries because the internal challenges of leadership—self-doubt, fear of failure, imposter syndrome—are universal.

Does Deborah offer group coaching or only private sessions?

Both. Private 1:1 coaching provides deep, personalized work tailored entirely to your situation. The Grounded Leadership™ Group Coaching cohort offers a structured 12-week program with peer support and shared accountability at a more accessible investment level. Many clients find a combination of both most powerful.

Where is Deborah located?

Deborah is based in the DC/Annapolis, Maryland area and works with clients globally via Zoom. All coaching sessions are conducted virtually, making location irrelevant to the quality of the work.

How do I know if I'm ready to work with an executive coach?

You're ready if you're a high-performer who recognizes patterns that aren't serving you, if you're preparing for or adjusting to a leadership transition, and if you're willing to invest in yourself and do the work. Coaching isn't for people seeking quick fixes or someone to tell them what to do—it's for those ready to develop their own capacity to lead with confidence.

25+ years

of coaching experience

 100 executive

coaching program director

Fortune

40+ years

 in nonprofit leadership

"Denver to Dubai"

Worked with leaders from

As a certified executive coach and fear mastery specialist, Deborah was handpicked by a Fortune 100 Chairman to direct their executive coaching program. She spent a decade in IT at TIAA and Prudential, building systems and training leaders through technological transformation...

"The work begins with fear mastery—the groundwork. From there, you develop grounded leadership—the capacity to lead yourself and others from clarity, not anxiety. And that's what enables you to raise your impact in every room you enter."

The International Coaching Federation reports that 99% of individuals who hire a coach are satisfied with the experience, and 96% would repeat the process. Companies investing in executive coaching see a median ROI of 7x their initial investment. (Source: ICF Global Coaching Study 2023)

Ready to Lead Without Self-Sabotage?

Whether you're here for a personal breakthrough, a career shift, or both—it starts with seeing yourself clearly. Not who you think you should be, but who you actually are when fear isn't driving the decisions. Everything else builds from there.

Let's Talk

As much as I love helping leaders transform their careers through executive coaching, I believe the greatest work I've ever done—or will ever do—is within the walls of my own home...

Organizations where I've coached leaders ready to lead from their strengths, not their fears.