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  1. Find a Coach
  2. United States
  3. Maryland
  4. Baltimore Area
  5. Annapolis

Jay Holley Annapolis, Maryland

Leadership Coach, Performance Coach, Executive Coach

MS

Driven leaders and high performers - whether rising, thriving, or stuck - ready to dig deep, break through barriers, and unearth their full potential through bold, purpose-driven growth.
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      Details

    • Location: Annapolis, Maryland 21409
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    • Hourly Rate: $75 to $125 US Dollars
    • Training: Anne Arundel Community College
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    About Me

    Reviews

    Have you worked with Jay? Tell your friends!

    2 reviews (5.0)

    June 24, 2025

    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
    June 24, 2025

    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

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