Gen. Stanley McChrystal Gives a MasterClass on Leadership

General Stanley McChrystal is a retired four-star general recognized for his transformative leadership of the elite counter-terrorism force, Joint Special Operations Command (JSOC), where he spearheaded the elimination of Abu Musab al-Zarqawi, the leader of the terrorist organization Al Qaeda.

McChrystal is celebrated for cultivating “a force of unprecedented agility and lethality,” and, since retiring, he has authored bestselling books, consulted with business leaders to unlock high-performing teams, and created a new class on MasterClass, “Battlefield Tactics for Business Success,” which promises to teach attendees how to “lead fast, build trust, and win under the highest of stakes.”

In the latest episode of How Success Happens, Gen. McChrystal — who insisted we call him Stan — shared his candid thoughts about the real meaning of leadership, decision-making under pressure, and the necessity of trust at every level of an organization. He shares the military mindset that has carried over into his business career — and also the two things about life in the Army he doesn’t miss. (Spoiler alert: burpees and liver for dinner.)

You can watch our entire conversation above or listen here. Check out the three battle-tested leadership strategies that Gen. McChrystal swears by.

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Lead by Example Every Day

McChrystal emphasizes that leadership isn’t about issuing commands but creating an environment in which others flourish: “Your value add is to create an environment in which the people that work with you and for you can be as effective as possible,” he says. “You’ve got to be an organization that they want to be a part of and a leader that they want to follow.” McChrystal says that leadership requires living values and sharing risks, and being willing to “pick people up, dust them off, and help them move forward” when morale dips.
Takeaway: Build a foundation of shared values and demonstrate consistent, hands-on leadership in every moment.

Decentralize Decision-Making

Reflecting on his command in Iraq and Afghanistan, McChrystal advocates for empowering teams at all levels: “You’ve got to push the decision down to the level where people are most informed.” Meaning, the literal or figurative boots on the ground who are carrying out the actual work. McChrystal also suggests sharing context — letting people know how this action impacts the overall picture — and encourages taking ownership of outcomes. He uses the term “radical transparency” and says that talking openly about successes and failures is crucial for building confidence in teams.
Takeaway: Give your team context and authority — and openly discuss good and failed results.

Accept—and Learn From—Failure

McChrystal says that every mission carries risk, and an aversion to failure “seizes up” organizations. He advises: “We expect failure. We accept failure. If you’re not failing a reasonable percentage of the time, you’re not doing enough.” He says this is easier said than done, and again, takes open communication, especially at the mid-tier of an organization.
Takeaway: Normalize failure as a catalyst for learning and encourage teams to stretch beyond their comfort zone.

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Fast Facts About Stanley McChrystal

• McChrystal’s family has a tradition of military service—both his father and grandfather were soldiers, making his career “never really a question” for him.

• He considers “The Longest Day” his favorite war movie, and admits to having a soft spot for rom-coms. “I really got into romantic comedies at a point because I just didn’t want to be thinking about all this heavy stuff all of the time. I like’ You’ve Got Mail.’”

• Despite a disciplined lifestyle, he admits to despising burpees and will “avoid them whenever possible.” And as for mess hall food that he doesn’t miss? Liver. Can’t say we blame him.

About How Success Happens

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.

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General Stanley McChrystal is a retired four-star general recognized for his transformative leadership of the elite counter-terrorism force, Joint Special Operations Command (JSOC), where he spearheaded the elimination of Abu Musab al-Zarqawi, the leader of the terrorist organization Al Qaeda.

McChrystal is celebrated for cultivating “a force of unprecedented agility and lethality,” and, since retiring, he has authored bestselling books, consulted with business leaders to unlock high-performing teams, and created a new class on MasterClass, “Battlefield Tactics for Business Success,” which promises to teach attendees how to “lead fast, build trust, and win under the highest of stakes.”

In the latest episode of How Success Happens, Gen. McChrystal — who insisted we call him Stan — shared his candid thoughts about the real meaning of leadership, decision-making under pressure, and the necessity of trust at every level of an organization. He shares the military mindset that has carried over into his business career — and also the two things about life in the Army he doesn’t miss. (Spoiler alert: burpees and liver for dinner.)