In this Mastermind episode of The Leadership Podcast, General Stanley McChrystal returns for a third conversation—his most personal and revealing appearance yet. Stan discusses the defining choices in his life, the moments that shaped his character, and the values that continue to guide his leadership. He talks about how his parents influenced his values through action, not words, and how his mother’s sudden death when he was sixteen changed the trajectory of his life and family. Stan shares his experience including near-expulsion from West Point, and another in his early Special Forces days when he learned that trying to be liked is not the same as leading well. Stan describes what it was like to work under leaders who lacked character, and how those experiences helped him define the kind of leader he never wanted to become. He discusses how having strong peers and a grounded spouse helped him stay true to his principles, even in environments where it was easy to lose direction. Stan shares how aging has narrowed his circle and sharpened his expectations for friendship. He also talks about how his views on war have evolved. He argues that true change in leadership and values may require discomfort or even crisis to take root. Stan shares why he believes society needs shared standards again—not to suppress individuality, but to maintain mutual respect and unity. Whether you’re a young professional, a seasoned leader, or someone thinking about the legacy you want to leave, this episode will challenge you to reflect. Stan reminds us that we’re not passengers in our own development. We can choose the kind of leader we want to be. You can find this mastermind episode wherever you get your podcasts! Watch this Episode on YouTube | Stan McChyrstal on Character https://bit.ly/TLPMM012 Key Takeaways [04:05] Stan shared how the foundation of his character was quietly built at home. His father, a combat infantryman, was steady and soft-spoken—the kind of man young Stan wanted to emulate. His mother, a thoughtful Southern woman, modeled integrity and social conviction. Stan said, “They never sat us down and talked to us about values… they just lived in a way that you thought, well, that’s the right way to go.” [07:11] Stan reflected on the emotional toll of losing his mother at 16. Her sudden death shook the entire family and deeply impacted his father, who, despite being a general and a warrior, visibly broke down. [09:01] When asked how he became the person he is today, Stan talked about trying on different leadership personas. He once tried being the “hard-ass” and even channeled General Patton, only to discover none of them fit. Eventually, through reflection and mistakes, he said, “At some point, there is a you, and you’ve got to sort of figure out what that is.” [11:43] Stan admitted that he came dangerously close to being expelled from West Point. It’s a story he laughs about now, but he acknowledged that if he hadn’t graduated, “we would not be laughing about it now.” [13:01] One of Stan’s earliest moral tests came during Ranger School. Exhausted and frustrated with a peer leader, Stan and a few others simply refused to follow orders. “There was a right and wrong… and we did the wrong thing,” he confessed. He’s carried the shame of that moment ever since, not because of the person they disrespected—but because he remembers what he did. [15:20] Stan looked back on his time as a young Special Forces lieutenant and admitted that he tried too hard to be liked. Over time, he learned that leadership isn’t about popularity—it’s about standards and setting the tone. A pivotal leadership lesson came when Stan was publicly fired by a seasoned commander after making a cocky remark in a meeting. “I’ve decided relieving you is wrong,” the major later told him. “You’re going to stay here, and I’m going to teach you to be an Army officer.” That humbling moment became a turning point—one Stan says he was lucky to receive. [20:19] Early in his career, Stan served under a battalion commander who taught him how not to lead. “He humiliated himself,” Stan realized, after being screamed at during a march. Later, that same leader quietly reenlisted an unfit soldier just to hit a metric—an act that shattered any remaining trust. “You don’t need a lot of examples like that to say: I will never do that.” [24:04] When asked if a public figure ever failed the character test, Stan said yes—and the disappointment stuck. “You start to say, well, if they’re really good at what they do, is it okay they do things they shouldn’t?” His answer: No. “Everybody’s got weaknesses… but there are bounds of acceptability,” and if someone crosses them, he simply steps away. [26:20] Stan shared that as he’s gotten older, his circle has gotten smaller. “I actually have a very small number of friends,” he said. While he’s become ...
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