This episode features a conversation with General Stan McChrystal ’76, Co-founder of the McChrystal Group.

Following his retirement from the US Army after 34 years, McChrystal founded the McChrystal Group, which is an advisory team that partners with businesses to improve the performance of their organizations and help build resilient and adaptable teams that can win in today’s dynamic environment.

A retired four-star general, Stanley McChrystal is the former commander of US and International Security Assistance Forces (ISAF) Afghanistan and the former commander of the nation’s premier military counter-terrorism force, Joint Special Operations Command (JSOC). He is best known for developing and implementing a comprehensive counterinsurgency strategy in Afghanistan, and for creating a cohesive counter-terrorism organization that revolutionized the interagency operating culture. As founder of the McChrystal Group McChrystal Group, he specializes in leadership consulting, leadership training, executive coaching, strategy alignment, team-building, transparency, communications, disciplined execution, networked organizations, and keynote speaking engagements.

In this episode, McChrystal talks about wanting to follow in his father’s footsteps to attend West Point and be a military hero. We learn about his initial struggles at West Point, and how he went from the bottom of his class to improve his standing on the Dean’s List. He provides insight about navigating life as a junior officer, and then as a general officer in high-stakes situations. McChrystal discusses a Rolling Stone article about his command group and how he handled the fallout and changes to his career that led to starting a new business. He also provides thoughts on mentorship, transitioning from the military to civilian life, and the importance of taking care of yourself.

Episode Timestamps

(01:44) Segment 1 – AAR
(02:05) Entry to West Point and Military Career
(02:59) First years at West Point
(07:59) West Point Academic Standing
(08:49) Meritocracy at West Point
(10:45) Mentors and Relationship with father
(13:30) Transitioning from Military and West Point
(15:55) Experience as a Junior Officer
(20:37) Progressing Through Ranks
(25:55) Time as Commanding and General Officer
(32:25) Building Mentorships
(35:45) Rolling Stone Article
(40:30) McChrystal Group
(41:27) Segment 2 – Sit Rep
(41:50) Running a Business
(44:45) McChrystal’s Big Four
(46:55) Empowering Teams
(48:45) Segment 3 – SOP
(49:15) Taking Care of Yourself
(54:45) Staying in Rhythm
(56:23) Foundations Built from Military and West Point
(57:55) Segment 4 – Giving Back
(59:45) Lessons from Sports