Tommy Sheppard
Coaching & Consulting

Strategic Coaching. Tangible Outcomes.

Insights That Lead to Impact.

You Bring the Quest.
We Build the Path.

Here to help you lead with confidence & purpose.

After more than 30 years in the NBA, including an incredible journey as President of Basketball Operations for the Washington Wizards, I’ve learned that leadership isn’t about titles—it’s about people. My career has been built on humility, hustle, and the belief that human connection is at the heart of every great team and organization.
 
These days, I’m channeling everything I’ve learned into helping others as an Executive Leadership Coach. Whether it’s guiding executives through change, helping teams find their rhythm, or mentoring the next generation of leaders, my goal is simple: to help people grow, thrive, and lead with purpose. I believe leadership is about listening, not just directing.
 
I’m also proud to teach Sports Leadership and Management at Georgetown University, where I’ve been an Adjunct Professor since 2009. Working with students who are passionate about breaking into the sports industry is one of the most rewarding parts of my career. It’s a privilege to share my experiences and help them build strong foundations for their own professional paths.

Coaching that aligns performance with purpose.

Leadership comes with both challenges and opportunities. 

Whether you’re striving to elevate your team, navigate change, or sharpen your decision-making, the journey to becoming the leader you aspire to be is a deeply personal and transformative process.

 
My role is to help you unlock that potential.
 
Having spent 30 years as an executive in the NBA, I’ve experienced firsthand the demands of high-stakes environments where leadership must be both strategic and adaptable.
 
That time equipped me with deep insights into high-stakes decision-making, team leadership under pressure, strategic thinking and talent development at the highest level.
 
Investing in your growth is one of the most impactful decisions you can make – for yourself, your team, and your organization.
 
I am here to support you every step of the way.

One-One Coaching

Personalized coaching to help you build self-awareness, overcome challenges, and lead with intention.

Executive Advisory

Strategic counsel for senior leaders facing high-stakes decisions, transitions, and growth opportunities.

Leadership Development

Elevate your leadership capacity with targeted growth strategies, career navigation, and mentorship.

Culture & Team Dynamics

Build stronger teams through improved trust, alignment, and culture-shaping leadership.

Organizational Change

Navigate transitions with clarity—whether it’s restructuring, scaling, or shifting strategic direction.

A structured approach to meaningful growth.

01. Chemistry Call

Let’s get to know each other. This initial call is a low-pressure opportunity to explore your goals, ask questions, and see if we’re a good fit to work together.

02. Goal Setting

We’ll co-create clear, personalized goals and outline a path forward—focused on what matters most to you and your leadership journey.

03. Coaching Sessions

Build momentum through focused, intentional work. Each session is designed to help you gain clarity, work through challenges, and apply insights in real time.

04. Ongoing Support

Growth doesn’t stop when the session ends. You’ll have continuous access to coaching support, accountability, and feedback as your goals evolve and new challenges arise.

Clarity starts with asking the right questions.

If you're exploring coaching, you probably have questions. You're not alone, and you're in the right place.

These are some honest answers to the questions I hear most often—from leaders who, like you, are ready to grow with purpose.

A leadership coach is a trusted partner who helps you grow your capacity to lead through clarity, feedback, and honest reflection.

My role is to help you navigate challenges, make better decisions, and lead with greater purpose and presence. Whether you're guiding a team, managing change, or evolving your leadership style, coaching provides the space and structure to do it intentionally.

Anyone in a position to influence others, including those who are leading a team, making high-stakes decisions, or stepping into a new role.

I work with senior executives, emerging leaders, and professionals navigating change.

If you're committed to growth and want to lead with greater clarity, purpose, and impact, leadership coaching can make a real difference.

My coaching philosophy is shaped by over 30 years of real-world leadership experience, including three decades in the NBA and more than a decade teaching at Georgetown University.

What sets my coaching apart isn’t just my résumé, it’s my approach. I believe coaching isn’t about giving advice; it’s about building trust, asking the right questions, and helping you find clarity in your own leadership style.

My role is to be a thought partner. Someone who listens, challenges, and walks alongside you as you grow.

Absolutely.

Confidentiality is foundational to the coaching relationship. Everything we discuss stays between us. This is your space to be honest, reflect openly, and work through challenges without judgment or outside pressure.

A little of both, but mostly the second.

My goal isn’t to give you quick answers, it’s to help you develop deeper clarity and confidence in your own decision-making.

I’ll ask questions, challenge your thinking, and share insight from experience when it’s helpful.

I believe the most powerful growth comes when you discover what’s already within you.