Something Extra Podcast with Lisa Nichols, CEO of Technology Partners

Episode 359: How Accountability and Humility Drive High-Performance Teams with Greg Wooldridge

Written by Insights Contributor | Nov 6, 2025 3:30:14 PM

What does it take to lead one of the most elite, high-stakes teams in the world? Retired U.S. Naval Officer and three-time Blue Angels Flight Leader, Captain Greg "Boss" Wooldridge, reveals the mindset required to lead pilots who fly inches from disaster. Discover how the Blue Angels harness the power of vulnerability and fearless feedback using a structured debriefing process to build radical trust and achieve peak performance. From the importance of being both confident and humble to the impact of finding a mission "bigger than just air shows," this is an indispensable masterclass in leadership.

Bio: Captain Greg Wooldridge served in the United States Navy for twenty-seven years. During the final decade of his career, he proudly served on three occasions as the flight leader and commanding officer of the Navy Flight Demonstration Squadron, the Blue Angels. In addition to leading the team for hundreds of air shows in the United States, Wooldridge took the team to various locations in Europe, including Moscow, Bucharest, and Plovdiv Bulgaria.

Greg received his high school diploma from Springfield High School in Springfield, Illinois, and immediately enrolled in Blackburn College in Carlinville, Illinois, where he earned his BA degree. During his career as a naval aviator, he was selected to attend Navy Safety School, and the Defense Language Institute (Spanish), both located at the Naval Post Graduate School in Monterey, California.

Typical of a career in naval aviation, Greg travelled across the nation many times, and made multiple deployments in aircraft carriers such as the USS Ranger, USS Enterprise, and USS Midway. He also lived in Subic Bay, Republic of the Philippines and Yokosuka, Japan as his naval career progressed. Greg commanded Navy Fighter/Attack Squadron 195 (VFA-195), and the Naval Air Station (NAS) Lemoore, California.

Between his tours as commanding officer of VFA-195 and NAS Lemoore - when his command was awarded the Presidential Installation of Excellence Award as the best navy base world-wide - he was selected to lead the Blue Angels. His initial selection for this elite command was through an extremely competitive process with other highly-qualified naval aviators just completing their initial fleet aviation command tours; his subsequent appointments to lead the Blue Angels were based upon his extremely successful initial tour as flight-leader and commanding officer.

Retiring from the Navy in 1997, Greg was hired by FedEx as a flight engineer and later became a line check airman and instructor. While at FedEx he implemented various aviation quality control elements in flight operations which significantly enhanced flight safety.

Greg specializes in delivering keynotes and workshops on high performance, teamwork, communications, and leadership. Clients have included FedEx, IBM, American Express, Mass Mutual, Chevron and others.

In 2018, answering the call to duty once again, Greg ran in the Oregon Republican primary for governor. Though he didn’t win, he was successful in elevating the tenor and content of political discourse. Greg has just taken on the role of the Director of Capitol Ministries in Washington state.

His latest endeavor is producing a documentary about the 75 years plus of excellence demonstrated by the Blue Angels.

While claiming his roots are in Springfield, Illinois, Greg is now a proud Washingtonian living in Vancouver, Washington with his wife Debra. Extremely active in community activities, Greg has served on the boards of the Oregon International Air Show, the Dorchester Conference, USS Ranger (CV-61) Foundation , the Chartwell Society, the Oregon Viet Nam War Memorial and the Blue Angel Foundation. Greg has just taken on the role of the Director of Capitol Ministries in Washington continuing to follow his passion to serve.

Something Extra: "Well, I'll go back to trust first of all. But you need to be confident and at the same time, be humble. Allow yourself to be vulnerable."

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