Episode 20: General Stanley McChrystal

An interview with General Stanley McChrystal about the biggest leadership myth, how leadership has changed, the most common leadership traits, why environment matters and his best piece of career advice. Welcome to the twentieth episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and […]

An interview with General Stanley McChrystal about the biggest leadership myth, how leadership has changed, the most common leadership traits, why environment matters and his best piece of career advice.

Welcome to the twentieth episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is former four-star U.S. Army General Stanley McChrystal. Born in Fort Leavenworth, Kansas, Stanley came from a line of military leaders, including his father who was a Major General and a grandfather who was a Colonel. He graduated from the United States Military Academy at West Point in 1976 and was commissioned a second lieutenant in the U.S. Army. That year, his initial assignment was to C Company, 1st Battalion, 504th Parachute Infantry Regiment, 82nd Airborne Division, serving as a weapons platoon leader. Two years later, he enrolled as a student in the Special Forces Officer Course at the Special Forces School at Fort Bragg, North Carolina. Then in 1981, he moved to South Korea as intelligence and operations officer for the United Nations Command Support Group and then became battalion operations officer. In 1990, he became action officer for Army Special Operations, working in Joint Special Operations Command, then a year later he saw action in the Desert Shield and Desert Storm tours. He was commander of the Joint Special Operations Command from 2003 to 2008 and became the top commander in Afghanistan in 2009, eventually resigning in 2010. McChrystal was awarded the Distinguished Service Medal and the Defense Distinguished Service Medal. Since his resignation, he has taught courses in international relations at Yale University, started his own company called The McChrystal Group, an elite advisory services & leadership development firm, and authored of multiple bestsellers including Team of Teams and Leaders: Myth and Reality. Stanley is on both Jet Blue and Navistar International’s board of directors and Chairman of the Board of Siemens Government Technologies.

The 5 questions questions I ask in this episode:

1. What is the biggest leadership myth?


2. How do you believe leadership has changed over the years and what’s stayed the same?


3. What common leadership traits do YOU share with those you interviewed for the book?


4. Why do different leaders require different environments?


5. What is your best piece of career advice?

Follow Stanley’s journey:

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