The Lesson I Didn't Expect - Rebecca Gray ’94

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