Admiral Sandy Winnefeld — Sailing Upwind: Leadership and Risk from TopGun to the Situation Room

Bill Gallagher

Whether you are leading only a handful of people or a team of thousands, challenges are an inevitable part of leadership. Today’s guest offers leadership advice from his time serving with the best of the best.


Admiral Winnefeld graduated from Georgia Tech with a degree in Aerospace Engineering and served for 37 years in the United States Navy. He flew the F-14 Tomcat and served as an instructor at TopGun and as senior aide-de-camp to General Colin L. Powell. He commanded a fighter squadron, the amphibious ship USS Cleveland, the aircraft carrier USS Enterprise, a carrier strike group, two NATO commands, the United States Sixth Fleet, the United States Northern Command, and the North American Aerospace Defense Command. He retired after serving as the ninth Vice Chairman of the Joint Chiefs of Staff.


Admiral Winnefeld is a frequently-published author and a director or advisor to companies operating in a broad spectrum of business sectors.


One of the greatest influences on Admiral Winnefeld’s time as an instructor at TopGun was positive peer pressure. He and his fellow instructors and pilots knew they were the best in the Navy and the community, so instead of constantly competing with each other, they held each other to a higher standard and helped each other reach it. Effective leaders not only support people where they currently are, but they also motivate them to become their best.


The first of the 5 Anchors of Leadership is Leading Yourself. Leaders must have a mission in mind and a desire to accomplish something, but that alone isn’t enough. The best leaders Admiral Winnefeld ever worked for exhibited integrity, courage, and genuine humility. Effective leaders never stop learning about their profession and refining their leadership skills.


Admiral Winnefeld highlights some of the challenges that are outlined in his new book Sailing Upward: Leadership and Risk from TopGun to the Situation Room. From difficult discussions to the changing demands of leadership style at various levels, he shares the experiences and evolution of his approach to leadership. He offers tactics for enhancing a company’s culture, the behavior of a leader that will elicit change, and how he could tell within the first 10 minutes whether a ship and its crew was a good one or not.


From the hardest leadership challenge he has faced to the best leaders he worked for and the advice from Colin Powell that shaped his entire approach to effective leadership, this conversation is filled with leadership advice from the best of the best.


Interview Links:

James A. Winnefeld



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Scaling Up is the best-selling book by Verne Harnish and our team for Scaling Up Coaches (formerly Gazelles). We share how the fastest-growing companies succeed where so many others fail.


Bill Gallagher, Scaling Coach and host of the show, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.


We help leadership teams with the biggest decisions around People, Strategy, Execution, and Cash so that they can Scale Up successfully and beat the odds of business growth. Scaling Up is based on Verne’s original best-selling business book, Mastering the Rockefeller Habits.


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