Jay Holley Annapolis, Maryland
Leadership Coach, Performance Coach, Executive Coach
Organizational Development and Leadership
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Annapolis, Maryland 21409
410-845-1349-
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- Hourly Rate: $75 to $125 US Dollars
- Training: Anne Arundel Community College
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Listen to Noomii's interview with Jay Holley
About Me
I grew up in a small town in West Texas and joined the Navy straight out of high school, trading open fields for open seas. Over the past 28 years, I’ve served with pride, purpose, and perseverance—but it was through helping others grow that I discovered my true passion: coaching.
Throughout my Navy career, I leaned heavily on mentors, advisors, and spiritual leaders to navigate life’s challenges—especially the lifelong struggle of undiagnosed ADHD. Their guidance helped me break through, and in time, I found myself becoming that support for others. I developed coach-like skills to help those who felt stuck, unsure, or simply ready to dig deeper and push toward their full potential.
I’ve received coaching training through Navy leadership programs and Columbia University, and I’m currently completing a professional coaching program aligned with ICF certification standards. These tools sharpen what I’ve already been doing informally for years—listening deeply, asking powerful questions, and holding space for real growth.
Now, as I prepare to retire from active duty, I’m launching a full-time coaching practice. This is more than a career shift—it’s a continuation of my calling to serve. I know firsthand how transformational coaching can be. If I’d had a coach all those years ago, I would’ve gotten further, faster. My mission now is to offer that same clarity, challenge, and care to others on their own leadership and life journey.
Reviews
2 reviews (5.0)
Ive had the privilege of calling Jay Holley a friend for more than 15 years, and recently I asked him to coach me through several professional and personal crossroads. Jays long career as a U.S. Navy Master Chiefculminating in his role as Brigade Senior Enlisted Advisor (Brigade Master Chief) at the U.S. Naval Academymeans hes led teams in some of the most demanding environments imaginable. What makes Jay exceptional as a coach, though, is that he never relies on that résumé to prescribe answers. Instead, he uses it to craft the right questions. Each session felt like an expertly guided conversation in which Jay drew out my own reasoning, surfacing the assumptions and blind spots I hadnt recognized. By the end, the insightsand the action planswere unmistakably mine, which made them stick. Jay balances candor with genuine care. He listens deeply, challenges gently but firmly, and offers perspective only after giving me space to think aloud. I left every meeting with sharper clarity about my goals and a renewed confidence in my decision-making process. If youre looking for a coach who leverages elite leadership experience while keeping the spotlight on you and your growth, I cant recommend Jay Holley highly enough.
Mike Hampton
I can't recommend Jay highly enough as a leadership coach. As a long-term friend, he's been an incredibly supportive and instrumental figure throughout my own leadership journey. Jay truly excels in his role. He's not only remarkably kind and thoughtful but also possesses a unique ability to ask profoundly insightful questions that genuinely encourage deeper reflection. What sets him apart is his authentic care for my success and well-being. He's consistently helped me gain new perspectives, challenging me to look at situations differently and fostering significant personal growth. If you're seeking a leadership coach who combines genuine empathy with expert guidance, Jay Holley is an outstanding choice.
Ryan Leahy
