When Rebecca Gray ’94 arrived at her first duty station, she thought she was ready to lead — until a senior master sergeant told her to get a coffee cup and led her away from the safety of her desk. “You’ve got to know who people are, so that you know how to relate to them,” he told her. That simple moment became the foundation of her entire leadership journey. 

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REBECCA'S TOP 5 LEADERSHIP TAKEAWAYS

1. Lead With Authentic Connection

Genuinely care about your team members as people, not just colleagues — know their stories, show real interest in their lives and let authenticity drive your leadership style. This builds trust and drives engagement.

2.Adapt and Balance Across Life’s Seasons

Recognize that leadership and career paths aren’t always linear. It’s important to intentionally adapt your role and focus to meet the current stage of your life, whether that means prioritizing family, professional growth or personal health.

3. Translate Core Values Across Environments

Military leadership lessons — like accountability, communication and team cohesion — are just as powerful in civilian life. Carry these values into new environments and roles, and tailor them to fit each unique context.

4. Empower Others Through Example

Be a “working leader” by setting the pace and modeling the behaviors you want to see. Encourage your team’s growth by giving responsibility, asking for input and trusting them to rise to new challenges — even if it means letting them make mistakes.

5. Continuous Self-Development Fuels Leadership

Commit to lifelong learning and personal development through regular habits — like reading, exercise and reflection. Maintaining intellectual curiosity and a growth mindset not only strengthens your leadership but also inspires others to do the same.

CHAPTERS

0:00:04 – Introduction to the Podcast and Guest Rebecca Gray



0:00:29 – The Coffee Cup Lesson: Early Leadership and the Influence of Senior Master Sergeant Kennedy



0:01:48 – Authentic Connection: Lessons Carried From the Military to Corporate Leadership



0:03:32 – The Power of Authenticity and Understanding Team Members’ Lives



0:04:49 – Translating Military Leadership Lessons to the Corporate World



0:07:58 – Creating Team Connection in Remote and Fast-Paced Environments



0:11:47 – Memorable Military Leadership Influences



0:13:24 – Balancing Military Service, Family and Career Transitions



0:16:53 – Career as Seasons: Crafting Balance and Intentionality



0:19:19 – Navigating Critical Career Junctures and Embracing Change



0:22:18 – Building Confidence and Trusting Yourself



0:23:46 – Fostering Confidence and a ‘Go Mentality’ on the Team



0:25:39 – Leading and Aligning Family and Professional Goals



0:27:28 – Practicing Continuous Learning and Personal Development



0:28:32 – Advice to Emerging Leaders: Value Well-Roundedness and Humility



0:29:43 – Reflections on Alumni, Family Connection, and Leadership Beyond the Academy



0:30:15 – Closing Thoughts on Leadership, Service and Authentic Paths

ABOUT REBECCA



BIO

Rebecca Gray ‘94, Boingo Wireless senior vice president and general manager, leads a division providing soldiers, sailors, airmen and Marines connectivity wherever they go. Alongside her military service, she’s held leadership roles at Fortune 200 companies in energy, media and telecommunications — including Southern Company and Comcast NBCUniversal — and has volunteered with multiple nonprofits. Her focus is on innovation that strengthens communities and keeps people connected.

A three-time All-American springboard diver, Gray started her Air Force journey as a recruited athlete at the U.S. Air Force Academy. After graduation, she trained as a World Class Athlete and competed for Team USA at the 1995 World Games in Rome. She’s served in key leadership roles across the Air National Guard and Air Force Reserve, including deputy wing commander at the 111th Attack Wing in the Pennsylvania ANG, as well as director of staff for the Georgia ANG. She’s also a graduate of the Secretary of Defense Fortune 500 Corporate Fellowship Program and earned her doctorate after studying around the globe in Israel, England, India and China.

She and her husband Christopher, a Class of 1993 Air Force Academy Grad, married at the Cadet Chapel in 1994. They have three daughters: Jasmine, a junior at Bates College; Grace, a sophomore at Centenary University; and Kennedy, a freshman at NJIT. Their Yorkie, Cookie, has become a seasoned traveler, having visited all but two states in the continental U.S.

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Wyatt Hornsby | Executive Producer:  Wyatt.Hornsby@USAFA.org 

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FULL TRANSCRIPT

OUR SPEAKERS

Guest, Rebecca Gray ’94  |  Host, Lt. Col. (Ret.) Naviere Walkewicz ’99

Naviere Walkewicz  00:04

Welcome to Long Blue Leadership, where we explore the lessons of leadership through the lives and stories of Air Force Academy graduates. I'm your host, Naviere Walkewicz, Class of ’99. When Rebecca Gray walked into her first duty station after graduating from the Academy, she thought she was ready to lead. But it wasn't a general, a colonel or a policy manual that changed her view of leadership. It was a senior master sergeant named Patrick J. Kennedy and a coffee cup.

Rebecca Gray  00:29

He said, “You're doing this all wrong. You need to be out, out, out.” He told me, “Go grab a coffee cup.” I didn't drink coffee at the time, so he goes, “Go get some water. Stop being difficult.” And he walked me around and said, “This is this is what matters. You’ve got to know who people are, so that you know how to relate to them.” That really shaped me.

Naviere Walkewicz  00:50

That simple moment became the foundation for how Rebecca has led her teams ever since. From the Air Force to corporate boardrooms, from public service to private equity, Rebecca Gray, USAFA, Class of ’94, has led across nearly every domain — active duty, Reserve and Guard — and built a remarkable second career spanning nonprofit work, education and now executive leadership. Her path has been shaped by transformational moments, moments that taught her how to connect, to trust herself and to lead with conviction. Rebecca, welcome to Long Blue Leadership.

Rebecca Gray  01:23

Thank you so much for having me. It's just a privilege to be here. Thank you for what you're doing for the grads, for the parents, for alumni, all of that. It's really impressive.

Naviere Walkewicz  01:31

Oh gosh. Really appreciate that. And I think, you know, that clip was so wonderful to hear. And I think we should just jump right in to that moment in time, kind of winding back the clock when you were just really transformed in your leadership style by your senior enlisted leader. Can we talk about that?

Rebecca Gray  01:48

I was just, had just graduated, and, as you said, my first duty assignment, and the only officer in the shop. And so senior master sergeant, which is one rank below chief — so the top, one of the top senior enlisted advisers in my shop, and we went for a walk and he really just taught me how to connect with the troops, to connect with people, walk around, get to really know them. And I'll have to tell you the first time I did it, I did a pass through, I went through the motions, if you will. And, you know, I came back, I was like, “Oh, OK, I did it. I d