The Leadership Podcast

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 less judgmental, he's also more selective. "I'm going to have people that I really respect and like—because that's who makes me respect myself." [27:50] Reflecting on whether younger people can shortcut the wisdom that comes with age, Stan emphasized the power of reading. Books like Once an Eagle offered different lessons at each stage of life. "Life is nuances forever," he said, and engaging with deep, thoughtful material can guide us when experience hasn't caught up yet. [28:54] Stan talked candidly about how his views on war have evolved. "Wars don't actually solve the problem that we hope they will," he said. After seeing combat firsthand, he became more cautious. But he also noted how those who sacrifice gain legitimacy in shaping national decisions. "They now felt legitimate," he said of Israeli soldiers after Gaza—ready to sit at the table. [34:13] Stan's call for a national conversation on character is rooted in concern for our systems. "We've let character erode," he said. Good people enter politics and emerge changed—warped by the system's demands. He doesn't believe politicians will lead this movement. "It'll start in schools, on teams, in churches," he said. "Most of you are not being the people you even want to be." [38:11] On the question of whether pain is necessary for change, Stan said plainly, "Yes, I think there has to be more pain." He saw it during the transformation of JSOC—reform only came during failure. While he believes powerful leaders could spark change, he warned, "The history of very powerful leaders is you get something you don't want." [39:35] Stan acknowledged the tension between individuality and unity. "There need to be standards of decorum," he said. He isn't advocating for hats and skirts, but for shared norms that show respect. "The society doesn't work without some kinds of rules," he warned—rules that give us common ground. [42:18] Stan offered this insight: "Who you are is not an accident… make it intentional." He believes we each have agency over our convictions and our discipline. His advice to young people: "Expect to stumble, expect to make mistakes… but move toward who you want to be. Don't drift." [45:07] And remember..."I think. Therefore I am." - René Descartes Quotable Quotes "A leader is not an individual rock that everybody comes around. It's a group of people, and you reinforce each other." "Everybody's got weaknesses… but there are bounds of acceptability." "Leadership is never about the leader. It's about the mission, the people, and the values we refuse to compromise." "Life has nuances forever." "Wars don't actually solve the problem that we hope that they will." "Who you are is not an accident. That just happens." "Make decisions on who you want to be and then move toward that." "Expect to stumble, expect to make mistakes." "Why do we allow politicians to lie to us when we know they're lying and they know we know it? Why do we put up with that?" "Becoming who you want to be starts with deciding what that is." "Character is the only metric that matters." "You may not control your physical surroundings, but you control your mind." "Reaching our convictions demands deep reflection." "The most critical discipline is to think for ourselves." Books mentioned in this episode: Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com General Stanley McChrystal Website | www.mcchrystalgroup.com General Stanley McChrystal X | @mcchrystalgroup General Stanley McChrystal LinkedIn | www.linkedin.com/company/mcchrystal-group Facebook | www.facebook.com/McChrystalGroup TLP101: General Stanley McChrystal on What Connects Us TLPMM002 - Part 1: General Stanley McChrystal (Ret) on Defining Yourself as a Leader

Sabina Nawaz is a top-tier executive coach who works closely with C-suite leaders and teams in Fortune 500 companies, government organizations, nonprofits, and universities globally. She's also the author of "You're the Boss: Become the Manager You Want to Be (and Others Need)." In this episode, Sabina discusses how power can distort perception, making leaders unaware of how they're coming across. She explains that the biggest barrier is often unacknowledged pressure, which leads to reactive behavior like micromanagement or overusing authority. She reveals how pressure can distort perception and lead to behaviors that harm both leaders and their teams. Sabina also dives into the tension between being approachable and maintaining authority, highlighting the importance of vulnerability and listening to others. She offers advice for leaders feeling overwhelmed, encouraging them to make time for "blank space" and reflect on their capacity before taking on more. For leaders looking to navigate the pressures of leadership and improve their effectiveness, this episode provides valuable insights on self-awareness, authority, and creating space for growth. You can find episode 464 wherever you get your podcasts! Watch this Episode on YouTube | Sabina Nawaz on Become the Boss You Want to Be https://bit.ly/TLP-464 Key Takeaways [04:18] Sabina shared how returning from parental leave led her into high-pressure meetings, causing her to shift from a supportive manager to a micromanager. A colleague's comment about someone crying because of her behavior made her reflect: "It's not power that corrupts—it's pressure." [06:53] Sabina warned against burnout from constant pressure. She advises high performers to set boundaries and practice "blank space"—two hours each week to unplug and just be. [08:51] Sabina emphasized the importance of balancing authority with empathy. She advocates for the "shut up muscle," where leaders wait to speak, allowing others to contribute first. [13:30] Sabina cautioned against claiming self-awareness. She encourages leaders to notice signs of power gaps, such as lack of independent feedback, as a way to improve awareness. [18:05] Sabina stressed that leaders should model vulnerability and avoid toxic positivity. Admitting struggles allows others to do the same, creating a more authentic work environment.She explained that leaders who hide their emotions prevent others from expressing theirs. Being open about one's own feelings fosters human connection, despite potential misinterpretation. [24:24] Sabina addressed the myth of bad bosses, stating that it's often pressure-induced behavior that causes leadership struggles. Leaders should adapt by reassessing how their strengths are perceived.Sabina urged leaders to reflect on how their strengths might be misunderstood under pressure. For example, "strategic" can be seen as manipulative and "calm" as disinterested. [28:03] Sabina highlighted the importance of reading signs from others and adjusting leadership behavior to avoid negative patterns and fit new responsibilities.Sabina shared a success story of a difficult leader who transformed by practicing restraint, slowing her pace, and valuing others' ideas—earning praise as the "best boss." [31:07] Sabina emphasized that coaching should come from genuine curiosity, not as an exit strategy. Only when leaders are willing to grow does true transformation happen. [32:32] Sabina offered a quick self-diagnosis tool from her book to spot "power gaps and pressure pitfalls," with reflective prompts like: "Are you the only one coming up with ideas?" [34:51] And remember... Know Thyself - Socrates Quotable Quotes "It is not power that corrupts. It is pressure that corrupts us." "Our default reaction to pressure is to hunker down and do more, more, more, more busier. But you know what? The 24-hour clock timer is going to die at some point." – "There are many ways to skin the cat. There are many ways to get something right and to accomplish something." – Sabina Nawaz "The first, second, maybe the third, fourth or fifth person to speak... Let others speak first because the minute you speak, no one else is going to debate that." "Self awareness is a never ending quest." "If somebody says they're self aware, they're not." "If someone says they're selfless, all I care about is everybody else... it's probably the opposite." "The more open you can channel yourself as the more people... It gives people permission to come to you and connect with you, human to human." "Be mindful of how you do that openness. And would you rather they're going to make up stories about you regardless whether you say something or you don't?" "It's more about diagnosing which specific aspect of bad boss behaviors are coming out in you when the pressure comes, the inevitable pressure comes in to corrupt you. But then it goes back to, you can't do any of that if you are not self aware." "There is no such thing as a purely bad or purely good boss." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Sabina Nawaz Website | sabinanawaz.com Sabina Nawaz LinkedIn | www.linkedin.com/in/sabinanawaz Sabina Nawaz Instagram | @sabinacoaching

Sibley Bacon is an applied researcher and functional artist, and shares how she blends creativity with structure to build more human-centered teams. Sibely describes what it means to be a "functional artist"—a leader who truly sees the big picture, connects deeply, and inspires through presence, not position. She reflects on lessons from her time at Google, where she worked on improving team dynamics and navigating the gap between theory and business reality. Sibley offers a new take on employee engagement: when people see their work as art, not just tasks, their connection to the purpose changes. She also shares why slowing down might be the most strategic move in a world driven by AI and speed—and why getting outside is more critical than ever. This episode challenges assumptions, invites deeper thinking, and offers a powerful mindset shift for anyone who wants to lead with heart and clarity. You can find episode 463 wherever you get your podcasts! We're now on YouTube… please subscribe! https://bit.ly/TLP-463 Key Takeaways [02:47] Jim asked about Sibley's journey, being a child of two artists yet pursuing math and science. Sibley shared that her home was one of high standards and creative discipline. Her father was a sculptor; her mother, a classical singer. She said, "If you're not doing art, what is the point of being alive?" For her, structure and excellence weren't negotiable—they were the minimum. Sibley remembered being asked about grad school at age nine. Her great-aunt had a PhD in Chemistry in 1935, so expectations were generational. That bar shaped her belief that nothing is off-limits if you approach it with discipline, humility, and openness. [05:54] Jim asked about what steered her toward tech. She recalled standing on a plaza at University of Maryland, looking around and realizing that "humans keep creating humans," and data would need to be stored digitally. It wasn't about passion—it was about self-reliance: food, shelter, and survival. That clarity fueled her path into software engineering. [07:29] Jan asked about being a functional artist. Sibley said being an artist is about seeing everything and feeling everything. Functional art, she said, is about creating elegant tools for mundane tasks—turning the ordinary into something purposeful and moving. "You have to absorb it all… and produce something people take note of." [09:11] Jan brought up tone and intention in leadership. Sibley believes leadership starts with love. She cited John Madden's wisdom—you have to know who needs encouragement, discipline, or nurturing. She said, "When your team knows you love them, and you're doing everything you can to support their creative success, they perform better." [11:49] Jim asked about her work at Google. Sibley said she approaches team effectiveness as an art form. At Google, she was both responding to and initiating change. She credited Dave Duffield (founder of PeopleSoft and Workday) with teaching her how to connect dots between software and business execution. She added, "If you don't want to learn and grow, you don't want to work on my team." [14:24] Jim explored what makes cultures thrive or struggle. Sibley noted that unclear missions and rules of engagement stall momentum. She contrasted Google's abundance and academic culture with her own background rooted in lean business execution—underscoring how resource environments shape behavior and accountability. [17:27] Jim asked about balancing creativity and discipline. Sibley explained that Google was designed for "starburst innovation"—parallel innovation across many disciplines. It took years, but she now sees how that environment was tailored for breakthroughs in AI, quantum computing, and neural networking. [21:26] Jan asked about negotiating engagement. Sibley flipped the phrase. "We need to go as slowly as we possibly can, as fast as possible," she said. It's not just poetic—it's tactical. Today's emerging workforce, shaped by digital native neurology, requires deceleration to connect, adapt, and lead effectively. [24:50] Jan asked about adaptability. Sibley emphasized customizing leadership. Some thrive remotely, others need community. "You're not leading static people," she said. "Their lives are dynamic. How they need you changes." To lead well, you must stretch your people—and stay one step ahead. [27:33] Jim asked how generations can collaborate. Sibley shared her commitment to being "a good ancestor." It means grounding innovation in what's real—like gravity—and connecting high-tech tools to basic human needs. She's working on building a "small business market exchange" to complement Wall Street with sustainability. [34:45] Sibley said humility was the hardest thing she's worked for. "I was born a Leo, the year of the dragon, in Texas," she laughed. "That doesn't set you up for humility." Her journey, she shared, is about making a living amends—and doing the work to serve others better. [36:02] And remember..."Every child is an artist. The problem is how to remain an artist once we grow up."-Pablo Picasso Quotable Quotes "with a global computing infrastructure, I think we need to go as slowly as we possibly can, as fast as possible." "Being an artist, you have to see everything. " "It's not your job whether or not they like it or not. It's about that they think about it." "Team execution effectiveness to support business sustainability. That is my art form." "Part of being a leader is being willing to negotiate." "We need employees to be adaptable. Everything's changing. At the same time, we need leaders to be adaptable." "So I think to be a leader means adapting to every single one of the people on your team, as their lives are dynamic." "I always want to be able to stretch people outside their comfort zone so that they can learn and grow." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Sibley Bacon Website | sibleybacon.com Sibley Bacon LinkedIn | www.linkedin.com/in/sibleybacon

Linda Ugelow is the author of "Delight in the Limelight: Overcome Your Fear of Being Seen and Realize Your Dreams." In this episode, Linda shares how fear often stems from past experiences, and how leaders can reframe internal narratives to demonstrate more confidence. She dives into the power of self-acceptance and how it shapes leadership presence, especially in high-stakes situations. Linda shares how leaders can embrace strategic vulnerability—being open without oversharing—to build trust and credibility. If you've ever doubted your voice, this conversation will challenge your assumptions and offer a path forward to speak with clarity and confidence. You can find episode 462 wherever you get your podcasts! https://bit.ly/TLP-462 Key Takeaways [01:29] Linda shared that before becoming a confidence coach, she was an organic farmer growing specialty vegetables for local restaurants. But ten years ago, she realized she was in the wrong business. She knew she wanted to make an impact, and rather than judge that desire as grandiose, she owned it and began her personal transformation journey. [03:10] Linda explains fear always has a reason. It stems from life experiences, cultural influences, and how we were raised. People might have been bullied, overlooked, or told to stay silent growing up—leading to ingrained beliefs like "It's not safe to be seen." Fear, she says, isn't the enemy; it's a messenger from the past. [06:16] Jim prompted the distinction between self-awareness and self-acceptance. Linda encouraged us to love the sound of our own voices—not to dominate but to take up space with intention. She frames presence as a balance between owning the moment and celebrating others' moments in the spotlight. [08:23] Leadership moments aren't always obvious. Linda encourages leaders to view these moments as service, not performance. If your voice might help move things forward, step in. The environment matters too—leaders must foster psychological safety if they expect others to contribute meaningfully. [13:01] Though she has a background in expressive arts therapy, Linda identifies as a coach. She helps people resolve deep-seated fears using tools like EFT (tapping), creative visualization, and inner forgiveness. Her process isn't traditional therapy—it's based on what worked to dissolve her own fear of being seen. [20:28] Linda explained that vulnerability looks different depending on the context—on stage vs. team meetings vs. watercooler chats. Her own experiences showed that being human—forgetting a point during a talk or making a mistake—can deepen connection and make you more relatable and trustworthy. [24:05] Jan asked how Linda helps leaders shift from fixed to growth mindset. Linda shared she overcame her fear at age 60. Her advice: start small, build confidence with tiny wins, and remove what's blocking you. Once the fear is cleared, skill-building becomes easier. "This is your life," she says. "Live it fully." [26:59] Linda wrapped with a powerful reminder: be your own best supporter. Silence your inner critic and give yourself permission to speak. Slow down, enunciate, and let your voice reflect the value of your message. People want to hear you—believe that, and speak like you do. [29:08] And remember..."We don't always have an accurate view of our own potential. I think most people who are frightened of public speaking and can't imagine they might feel different as a result of training. Don't assume you know how much potential you have. Sometimes the only way to know what you can do is to test yourself." - Scott Adams Quotable Quotes "Fear is not the villain. Fear is a messenger." "We need to not feel the pressure that we have to be a 10-year experienced speaker when we are just starting out." "Self-expression and speaking is your human design." "It's never too late. I overcame my fear of speaking when I was 60 years old." "The world opens up to you when you remove all the blocks." "Be your biggest advocate. Your staunchest supporter." "If we're going to bother to say it, let our words be heard." "Perfect does not make us human." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Linda Ugelow Website | www.lindaugelow.com Linda Ugelow YouTube | www.youtube.com/user/lindaugelow Linda Ugelow TikTok | @lindaugelow Annotated Speaker Preparation Checklist to feel grounded, focused, and energized when you speak. www.lindaugelow.com/rituals Delight in the Limelight podcast | https://lindaugelow.com/ditl-podcast Linda Ugelow Facebook | www.facebook.com/linda.ugelow Linda Ugelow LinkedIn | www.linkedin.com/in/lindaugelow Linda Ugelow Instagram | @lindaugelow

In this episode, Jim and Jan dive into the critical aspects of leadership and talent development in today's fast-changing work environment. They discuss how companies often seek "unicorn" candidates with unrealistic expectations—and why focusing on core traits like emotional intelligence, curiosity, and continuous learning is essential. Jim and Jan explore how hybrid work is reshaping the workplace and why relationship-building, trust, and clear expectations are key to fostering strong teams. They also examine how job seekers and employers often set themselves up for failure by chasing perfection. Jim and Jan Jan also offer practical advice on how to set clear career and hiring expectations, why adaptability is critical, and how small shifts can create big growth opportunities. If you're leading a team, looking to hire, or thinking about your own career moves, this conversation offers a practical, honest look at what really matters—and what doesn't. https://bit.ly/TLP-461 Key Takeaways [01:41] Jim explained that companies often search for "unicorns"—candidates who meet every requirement, even unrealistic ones. Jan emphasized that a core leadership responsibility is attracting, selecting, and developing talent—not just hunting for perfection on paper. [03:05] Jim and Jan agreed that many hiring managers are too focused on what candidates lack instead of what they bring. Jim pointed out that companies over-index on skills and miss out on key attributes like curiosity and a willingness to learn—traits that often matter more long term. [06:03] Jim noted that just like companies are looking for unicorn candidates, job seekers are hoping for unicorn employers. Jan laid out four traits to watch for in great talent: passion and purpose, a mindset of continuous learning, emotional intelligence, and the ability to build strong networks. [08:19] Jim talked about the difficulty of building relationships in a remote setting—especially without emotional intelligence and strong listening. Jan compared early career years to middle school: it's when people learn how to navigate politics, influence, and presence. That kind of social learning took a hit during the pandemic. [10:45] Jim predicted that smaller cities might thrive post-pandemic due to shorter commutes and easier transitions back to the office. He sees hybrid work staying, but believes 20-somethings still need in-person time to develop foundational business skills. Jan added that many teams are struggling with connection and accountability. He emphasized that relationship-building can't be hacked—it takes real time, trust, and personal conversations about more than just work. [14:31] Jim shared a story of young professionals rejecting work based on industry, pointing to unrealistic expectations. Jan reminded listeners that companies hire to solve problems, not to fulfill career wish lists. They discussed the importance of setting clear expectations upfront and embedding key traits like initiative into the hiring process. [16:46] Jan stressed that avoiding early-career sacrifices often limits options later on. Jim explained that career growth follows a narrative arc: in your 20s, your value is effort; in your 40s, it's your experience; and later, it's wisdom. Each stage requires a different approach. [20:08] Jim raised the issue of age bias in tech and why staying visible matters. Jan agreed—saying that visibility is key to growth. He advised looking at who gets promoted and understanding what behaviors and values those people have in common. [23:49] Jan recommended using the Topgrading method when hiring, which emphasizes past performance over future potential. He highlighted three key things to assess: impact, influence, and cultural fit. Setting clear expectations during interviews is critical. [26:45] Jan brought up a striking stat—the largest voting gap in the last election was between educated women and uneducated men. Jim clarified that he wasn't suggesting anyone should "settle" in relationships. Instead, both agreed that knowing your non-negotiables is essential and that no partner—or hire—is perfect. [27:52] Jan explained that mismatched expectations usually come down to poor communication. Most people talk more than they listen, and few ask the right questions. Interviewing is a skill—one that both sides often fail to prepare for. [29:15] Jim encouraged listeners to focus on what really matters and avoid perfectionism. He warned that "perfect is the enemy of progress," especially when making hiring decisions or career moves. Overthinking often leads to doing nothing. [30:14] Jan shared a coaching example where a leader needed to clarify expectations around initiative. Not everyone grows—and if they don't, they may no longer be a fit. He pointed out that adaptability is critical, especially in today's ever-changing, chaotic environment. Organizations evolve fast, and employees must be willing to shift with them. Jim agreed—saying that people who enter a company with their own fixed agenda often struggle to adapt. [32:54] And remember..."A man travels the world over in search of what he needs and returns home to find it." - George A. Moore Quotable Quotes "One is to get results. Two is to behave and act according to the core values... But there's a third leg and that third leg is to attract and select talent. And then once you have them, to develop and retain said talent." "People just aren't finding what they're looking for. But on the flip side, employees are also looking for the unicorn employer, you know, something that doesn't exist." "If people aren't able to develop power and influence in the organization, they are not going to get stuff done... They're going to have to be able to negotiate and sell ideas." "There's no hack to accelerate the development of relationships other than spending time with people." "The interview you're about to do is not about you. It's about their problem." "Everybody's hired for the same purpose. Get and keep customers." "A good life is lived in the service of other people." "You got to realize your value isn't from hard work, your value is from wisdom and knowledge and experience." "what really transpires between people looking for the perfect person and people looking for the perfect company is there's misaligned expectations." "So, you know, for expectations to be aligned, you know, both sides have to do their homework and prepare, ask a lot of questions, be good listeners." "Perfect is the enemy of Progress." "not every position needs a perfect person." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com TLP376: The Key to an Uncommon Company with John Harrington and Dave Pickhardt

Susan Kelsey has authored four historical books and produced the award-winning documentary, "The Negotiator: Billy Caldwell." In this episode, Susan shares her journey of discovering Billy Caldwell, the "Great Negotiator" of early Chicago. She reflects on the leadership lessons she learned from both Caldwell and Native American leaders, focusing on values like moral courage, tenacity, and the importance of handling success and failure with grace. Through her work with Native American tribes, Susan has gained a deeper understanding of leadership—one rooted in respect, curiosity, and self-awareness. She talks about the vital role storytelling plays in leadership and how it can make complex ideas more relatable. Driven by a lifelong curiosity, Susan shares how her hands-on experiences, like earning her pilot's license and working on documentaries, continue to shape her perspective on leadership and learning. Tune in to hear her insights on the wisdom of elders, the value of cultural understanding, and how these lessons inform modern leadership today. https://bit.ly/TLP-460 Key Takeaways [04:06] Susan's journey with Billy Caldwell began after noticing a plaque in her neighborhood. Over 30 years, she learned about Caldwell's role as a negotiator between Native Americans and European settlers, shaping Chicago's history. Caldwell's unique position allowed him to influence key treaties, including the 1829 and 1833 Treaties, which played a major role in the region's development. [07:03] Susan described Billy Caldwell as the "ultimate glue guy," bridging cultural gaps between Native Americans, military settlers, and Europeans. His ability to understand both worlds helped him play a key role in negotiating important treaties for the Chicago area. His military background and unique perspective made him a crucial figure in shaping Chicago's history. [09:29] Susan believes strong moral values and the willingness to stand for one's beliefs, even at personal cost, set leaders apart. She emphasized that leaders like Billy Caldwell had the courage to take risks for the greater good. Moral leadership is key to achieving lasting change and making a positive impact. [10:53] Building trust with indigenous tribes took years of effort for Susan, including traveling to Kansas and embracing vulnerability. She learned that respect, curiosity, and open communication are essential in fostering meaningful relationships. Developing trust takes time, but it's vital in working with diverse communities. [13:52] Susan's persistence paid off when the Potawatomi tribe eventually approved her revised documentary. She learned that tenacity is key, especially when working through rejection. A surprising conversation with the tribe revealed that they didn't see the loss of the Great Lakes as a loss, challenging Susan's understanding of their culture. [15:28] Susan emphasized the importance of listening more than speaking in cultural interactions. She explained that silence is highly valued in indigenous communities, and actively listening can build trust. Reflecting back what's heard fosters stronger relationships and a deeper understanding. [18:38] When Jan asked about her motivations, Susan revealed that lifelong curiosity drives her pursuits. She believes true learning comes from hands-on experiences, not just books or videos. Her curiosity led her to earn a pilot's license to confront her fear of flying, highlighting her need to fully immerse herself in new experiences. [19:47] Susan never tires of filmmaking, as it allows endless creativity. She loves collaborating with Native American musicians to create meaningful soundtracks for her documentaries. Despite the high costs of filmmaking, she finds ways to fund her projects and emphasizes that the value of a story doesn't depend on the budget. [21:07] Susan learned timeless wisdom from her work with Native American cultures, especially regarding grace in leadership. Handling both victories and defeats with dignity leaves a lasting impression. She learned this lesson through political mentors and experiences with Native American tribes, emphasizing grace as essential in leadership. [23:09] Susan explained that Native American cultures view leadership as more than survival—it's about self-awareness. The Blackfoot Indians' perspective on Maslow's hierarchy, which prioritizes self-awareness over basic needs, challenged Susan's thinking. This worldview has shaped her understanding of leadership and personal growth. [24:57] Storytelling is a powerful leadership tool, helping leaders connect with others and make complex ideas relatable. Susan stressed that modern leaders should listen to elders, especially in uncertain times, for their valuable insights. Native American cultures offer wisdom that can guide today's leaders through challenging situations. [27:07] When asked about becoming an elder, Susan shared that the title is a great honor in Native American cultures. Elders are respected for both their age and the wisdom they have gained over time. She contrasted this respect with how older generations are often treated in other societies, underscoring the value of experience. [28:26] Susan's documentaries aim to spark meaningful conversations and encourage people to learn from one another. She highlighted the importance of curiosity and education in her work. Slowing down and reflecting on new ideas can provide valuable insights in today's fast-paced world. [30:41] And remember..."When it comes your time to die, be not like those whose hearts are filled with the fear of death, so that when their time comes, they weep and pray for a little more time to live their lives over again in a different way. Sing your death song and die like a hero going home." - Chief Tecumseh Quotable Quotes "We just need to be curious about each other, learn about each other and respect each other and... and develop that trust where we can have a nice, healthy, honest conversation." "How you hold yourself and the grace that you have is what people will remember." "We know who we are, we know where we came from, we know where we're going, and so we know if we know who we are, we can do anything. We can find food, we can find shelter, we can build community." "Slow down a little bit. You can back up, even put it down for a day, come back, look at it the next day. Perspective." Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Susan Kelsey Website | http://susankelsey.com Susan Kelsey's award-winning documentary, The Negotiator: Billy Caldwell. | thebillycaldwellmovie.com Susan Kelsey Facebook | www.facebook.com/susan.kelsey.39 Susan Kelsey LinkedIn | www.linkedin.com/in/susanlkelsey

Adam Contos is a former SWAT leader turned CEO, leadership advisor, and author of "Start With a Win: Tools and Lessons to Create Personal and Business Success." In this episode, Adam begins by defining a "win" in leadership not as just hitting KPIs or completing projects, but as creating momentum through small, daily victories. Adam stresses the importance of fostering a culture of accountability within teams, but without micromanaging. He explains that accountability is about creating an environment where people can succeed, rather than policing behavior. When discussing setbacks, Adam reminds us that challenges are inevitable, but it's how leaders respond that defines them. Instead of reacting emotionally, strong leaders respond thoughtfully, seeing setbacks as opportunities for growth rather than roadblocks. Adam also discusses how to sustain momentum, and highlights how constant, small improvements drive long-term results. Adam's insights provide a fresh approach to leadership, showing that small, consistent actions over time can build lasting success. If you're ready to implement these principles in your leadership journey, this episode is a must-listen. https://bit.ly/TLP-459 Key Takeaways [05:22] Jan asks Adam to define a "win" in leadership. Adam clarifies that a win isn't just about KPIs or project completions. Instead, he believes it's about creating momentum. He calls them "micro wins," like waking up before the alarm. Small wins add up, laying the foundation for bigger successes down the road. [06:34] Jan asks what shifts momentum for a team. Adam points to emotional intelligence, learning from failures, and adjusting strategies. Leaders help create a culture of confidence and resilience, guiding their teams to focus on strengths and not dwell on setbacks. [07:59] Adam shares that successful leaders don't leave their days to chance. They start by setting clear priorities, communicating expectations, and modeling discipline. Jan asks if leaders should set boundaries or let teams determine their own priorities. Adam says it's a mix. Leaders need to define expectations and values, but also give teams the flexibility to make their own decisions. [11:39] Adam explains that accountability isn't about policing; it's about creating an environment where people can succeed. Jan references a past guest who discussed the difference between what people want to do versus what they should do. He asks Adam how leaders can handle high-potential individuals who resist extra responsibility. Adam suggests challenging teams to grow while respecting their individual aspirations. Success isn't a one-size-fits-all, and leaders must find the right balance between encouragement and autonomy. [15:16] Adam responds to the question about handling setbacks by saying that volatility and challenges are inevitable in all areas of life. What defines a person is how they respond. He reminds himself that each setback is just a chapter, not the whole story. Strong leaders see adversity as a stepping stone, not a stopping point. He stresses the importance of responding thoughtfully, not emotionally, to setbacks and learning from them for the future. [18:07] Adam explains that leaders are made, not born. Instead of testing people under stress, leaders should train them to handle pressure by gradually increasing their exposure to challenging situations. This builds the skills and confidence needed to handle future stress. [22:22] Jan asks how leaders balance confidence and humility. Adam says confidence without humility can lead to arrogance and failure. He explains that the balance shifts depending on the audience and context. For instance, sales teams may need more confidence, while executive teams might appreciate more humility. [24:18] Adam talks about executive presence, which is about gravitas, communication, and appearance. He shares how Jamie Dimon commands a room without saying a word, demonstrating the power of presence. Adam advises leaders to always show up prepared, look like they care, and deliver messages that resonate with their audience. [27:01] Adam explains that success creates momentum but warns that it can also lead to complacency if leaders think it will sustain itself. He stresses the need for continuous improvement to prevent stagnation. Adam points to Team Sky's cycling success under Sir David Brailsford, where the focus was on constant, small improvements. Successful teams are driven by a mission, not just results. [34:58] Adam concludes by encouraging people to focus on creating wins every day. He emphasizes the importance of prioritizing actions that lead to positive results, rather than getting stuck on unproductive tasks. He advises adopting a proactive mindset and viewing daily tasks as opportunities, not obligations. [36:47] And remember..." Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win. " - Sun Tzu Quotable Quotes "A win isn't a KPI. A win isn't completing a project. A win more than anything is just creating momentum." "Successful leaders don't leave their day to chance." "If you walk in and sit down at the table in a meeting and you're pounding your fist and cussing things like that, guess what? The employees are going to do that. They're going to pound their fist and cuss at things when you're not in the room." "Great leadership starts before the first meeting. It's built in the moments of preparation and personal discipline." "I think you should allow people to spread their wings and fly as high and far and fast as they possibly can." "Accountability isn't about policing." "We need to create an environment where people can be as successful as they want to be." "volatility and setbacks have happened since the beginning of time. But ultimately you have to understand they don't define you. Your response to them is what defines you. " "Great leaders really train themselves to see adversity as kind of a stepping stone and really not a stopping point in their career and their life." "I think you can start putting pressures on people to see how they start to respond. And frankly, you can educate people. Leaders are made, they're not born." "Anyone can be taught, but it's hard to teach someone who doesn't want to learn." "if you have confidence without humility, it becomes arrogance, and that's when you get your butt kicked." "Know your audience, show up like a leader. I don't care where you're at, show up like a leader, look like you care and like you tried, and then deliver a message that resonates with your audience." "Success breeds complacency if you let it." "The best teams just don't work for results. They work for a mission. And if that mission is continuously developing and improving, they're probably going to continue to win because they're continuing to revitalize that momentum." "But the reality is the big guy started as a little guy at some point also, they just perpetually were able to ignore the losses that they were facing." "Set a culture, be a good person and live that culture. And if people like it, great. If they don't, great." "Focus on being better at a leader, as a leader, and focus on taking one more step towards your accomplishments." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Adam Contos Website | www.adamcontos.com Adam Contos | START WITH A WIN Podcast Adam Contos X (Twitter) | @adamcontosceo Adam Contos Facebook | www.facebook.com/AdamContosCEO Adam Contos LinkedIn | www.linkedin.com/in/adamcontos Adam Contos Instagram | @adamcontosceo

Pippa Begg, is the co-founder and CEO of Board Intelligence and co-author of "Collective Intelligence: How to Build a Business that's Smarter than You." In this episode, Pippa discusses the mindset shifts required for leaders to let go of control and empower others, emphasizing the dangers of hubris and the importance of questioning one's own authority. She also addresses the common struggle with delegation, advising leaders to trust their teams and ask powerful questions that drive innovation and collaboration. Pippa dives deep into the topic of communication, sharing a powerful example of how poor communication cost a brilliant opportunity. Pippa explains how AI can enhance decision-making in boardrooms by supporting human intelligence and uncovering biases, rather than replacing human input. When discussing power struggles in the boardroom, Pippa explained that they often arise from misalignment on what's important, especially regarding value creation. Pippa talks about the importance of balancing focus with flexibility, and shares how organizations can continually assess their strategies, asking the right questions that allow the organization to adapt to dynamic markets. This episode is especially relevant for senior leaders looking to develop resilient businesses that thrive in an ever-changing world. https://bit.ly/TLP-458 Key Takeaways Quotable Quotes "The pace of AI development can call all of that out. So really the thing that's blocking progress here is not the pace of technology. It's the pace of human adoption." "Humans don't take perfect decisions. We know about unhelpful decision making heuristics that we use. We know about bias that we have." "We are better when we're being observed than when we're not being observed." "We rush to find the answer... and often what we're doing there is we end up rushing to find an answer to not quite the right problem." "Many amazing business successes. The idea did not come from the CEO or from the board." "Most of the time when there is border and power struggles, it's because there's misalignment on what's important." "If we are willing to expose our thinking, if we are willing to expose our writing, if we are willing to expose our conversations, then not only could we be prompted, but we can just hold a mirror and just see what we're doing, really reflect on it." "Focus is absolutely critical to an organization's success, but blind focus can be its downfall, as we saw with Nokia." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Pippa Begg Website | www.boardintelligence.com Pippa Begg Recent Sunday Times profile (UK): www.thetimes.com/business-money/entrepreneurs/article/we-used-word-of-mouth-to-help-our-business-take-flight-0n2t6cbh9 Pippa Begg Recent research published into board effectiveness: www.boardintelligence.com/blog/the-state-of-board-effectiveness-in-2025 Pippa Begg Latest BI fundraise: www.boardintelligence.com/blog/board-intelligence-strategic-growth-partnership-with-k1-investment-management Pippa Begg LinkedIn | https://uk.linkedin.com/in/pippa-begg

Giles Watkins—coach, speaker, and author of "Positive Sleep: A Holistic Approach to Resolve Sleep Issues and Transform your Life (Positive Wellbeing)." In this episode, he explores why quality sleep is essential for high performance, decision-making, and long-term success. He dives into sleep's role in workplace culture—how it affects performance, decision-making, and even global business operations. Giles discusses how different cultures view sleep, how leaders can help their teams without overstepping personal boundaries, and why some companies are incorporating naps into the workplace. If you've ever struggled with sleep, wondered how to optimize your rest, or lead a team that could benefit from better sleep habits, this episode is packed with insights. https://bit.ly/TLP-457 Key Takeaways [02:34] Giles explains that while awareness around sleep has improved, people are still sleeping an hour less than they did 50 years ago. He attributes this to distractions like artificial lighting, phones, and technology. While the body can physically recover from lost sleep, the brain does not regain the same benefits, such as memory consolidation and emotional processing. [09:09] Jan asks Giles to define sleep, referencing Part 2 of his book. Giles shares a definition from Harvard Medical School, describing sleep as a reversible state where activity decreases, external responsiveness drops, and the brain undergoes essential restoration processes. He emphasizes that modern sleep science is still evolving, with ongoing debate about its full impact on cognition, learning, and mental health. [16:09] Giles explains that sleep needs gradually decrease with age, but the change is not dramatic. Factors such as genetics, environment, and personal habits play a role. Some people naturally need less sleep, while others struggle with shifting rhythms over time. He highlights that recognizing these differences is key for leaders managing diverse teams with varied sleep patterns. [23:37] Jan shares his experience in the military, where sleep deprivation was common, but he personally struggled with it. Giles confirms that while some individuals can push through exhaustion, it is not sustainable. He compares chronic lack of sleep to "social jet lag," disrupting natural rhythms and leading to lower motivation, reduced focus, and diminished quality of work. [27:58] Giles recalls his first experience working in Vietnam, where employees would nap under their desks after lunch. Initially shocked, he later realized it was an effective way to recharge. He contrasts this with Western cultures, where working through lunch is often seen as a sign of dedication. Businesses with global teams need to be aware of these cultural differences to maximize productivity. [36:37] Giles highlights the importance of bedtime routines—consistent sleep schedules, limiting screen exposure, and wind-down activities. He notes that many adults with sleep issues lost their childhood sleep habits after leaving home. Encouraging good routines in children can set them up for long-term sleep success. [41:19] Giles states that 80% of sleep problems can be resolved with behavioral changes, such as reducing screen time before bed, avoiding alcohol late at night, and sticking to a consistent schedule. He advises leaders to treat sleep as a priority, just like diet and exercise, to enhance their performance. [43:14] And remember, Sleep is that golden chain that ties health and our bodies together. - Thomas Dekker Quotable Quotes "We've evolved as a species, but we haven't evolved to sleep an hour less than we did 50 years ago." "Leaders assume their teams are like them. Some love breakfast meetings, some don't. Some don't mind late-night emails, others do." "The one long sleep is a post-industrial idea. Before factories, people often had two sleeps with a break in between." "The French have an expression that translates as 'the bicycle in your head.' To sleep well, you have to get off the bicycle." "You can survive with bad sleep, but you won't thrive." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Giles Watkins Website | www.positivesleep.co.uk Giles Watkins LinkedIn | www.linkedin.com/in/gileswatkins

Jamie Beaton is CEO of Crimson Education, helping students gain admission to top universities. A Harvard, Stanford, Yale, and Princeton graduate, he also founded Crimson Global Academy and authored "ACCEPTED! Secrets to Gaining Admission to the World's Top Universities." In this episode, Jamie reveals the mentors who shaped his leadership, including legendary investor Julian Robertson, and explains how to accelerate growth as an emerging leader. He discusses the challenges of leading a global company, how cultural differences impact leadership, and what truly defines top talent beyond credentials. He also dives into the "curiosity switch"—the key to staying relevant, inspired, and continuously learning. Jamie shares a pivotal moment in his leadership journey—balancing the demands of running Crimson while attending Stanford Business School, a decision that tested his resilience and investor relationships. He also provides insight into how leaders can build high-performance teams, manage ambition without burnout, and create a culture of excellence and execution. If you want to learn how to lead with curiosity, build a world-class team, and navigate high-stakes decisions, this episode is a must-listen. https://bit.ly/TLP-456 Key Takeaways [02:43] Jamie shares his love for Warhammer, a strategy board game that takes him across the world to compete. He finds it a great way to disconnect from work and engage in a different kind of strategic thinking. [03:58] Jamie credits Julian Robertson, founder of Tiger Management, as a major influence. Julian took him under his wing, instilling confidence in his abilities and teaching him the balance between competitive drive and integrity. [08:58] Jamie's experiences across countries like New Zealand, China, Singapore, and the U.S. have broadened his leadership perspective. He emphasizes that while leadership principles are universal, cultural differences impact feedback styles, work ethics, and hierarchical structures. Leaders must adapt to these variations to be effective. [11:35] Jamie highlights feedback styles as one major cultural difference. In places like Japan and China, direct feedback can be seen as disrespectful, while in the U.S. and New Zealand, a blunt and fast-paced communication style is more accepted. Work ethic expectations also differ, with China's 996 culture (9 AM – 9 PM, six days a week) contrasting with New Zealand's emphasis on work-life balance. However, he believes that people everywhere are drawn to ambitious, high-performance teams. [15:01] Jamie introduces the "curiosity switch", explaining that some people are naturally driven to learn while others become complacent. He believes curiosity can be reignited by exposing yourself to new industries, ideas, and challenges. Leaders who continuously push themselves to learn remain relevant. [17:38] Jamie admits that his rapid thinking once created chaos within his teams. Over time, he built a leadership team with specialized roles—some focused on executing ideas, while others thrived in early-stage innovation. By structuring his organization this way, he ensures creativity doesn't disrupt operational stability. [21:09] Jamie values learning agility, ambition, and integrity over academic credentials. He shares a story about his co-founder, Fungzhou, who started with limited English at 18 and now manages hundreds of employees globally. He believes top talent is defined by their ability to adapt, seek feedback, and push beyond their comfort zone. [25:43] Jamie acknowledges that in the early years, he wasn't easy to follow. To improve, he surrounded himself with strong communicators who could translate his vision into clear, actionable steps for the team. Over time, he became more aware of how his leadership style impacted others, ensuring his team had the clarity they needed. [27:11] Jamie has learned that face-to-face time is irreplaceable. He prioritizes in-person interactions with his executive team and country managers, even flying 18 hours for a two-day event. He believes that an hour in person builds more trust than 30 hours on Zoom, making these investments critical for leadership success. [29:22] Jamie describes the tension of balancing business school at Stanford while leading Crimson. His investors were skeptical, fearing it would be a distraction, while his team worried about his physical absence. Despite these doubts, Jamie pushed through, believing the skills and networks he gained would ultimately help Crimson grow. [34:01] Jamie credits his responsibility to his team, ambition, and the support of his co-founders as his guiding forces. He emphasizes that having trusted partners who can step in when needed is critical for sustaining leadership over the long haul. [37:02] Jamie explains that when your curiosity switch is on, work feels exciting and effortless. When it's off, every task feels like a burden. To reignite curiosity, he advises evaluating your work, relationships, and digital habits, ensuring you remove anything that drains your energy. [39:26] And remember, "An investment in knowledge pays the best interest." - Benjamin Franklin Quotable Quotes "People love to be on a winning team.You know, I think if you have that fast-paced intensity, ambitious goals, the ability for fast career progression, fast learning, you know, that is addictive to people anywhere and that's definitely very infectious." "You don't view feedback as some sort of negative thing, but actually as sort of like this addictive fuel for more growth." "When the curiosity switch is on, every day you're working, it doesn't feel like you're working. You know, it feels like this exciting, adrenaline-packed, exhilarating adventure." "If you're in the wrong lane, staying there longer won't fix it." "I think the most notable thing about different cultural backgrounds or a couple, but one of them would be how you give feedback." This is the book mentioned in this book Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Jamie Beaton Website | crimsoneducation.org Jamie Beaton LinkedIn | www.linkedin.com/in/jamiebeaton Jamie Beaton Instagram | @jamiebeaton.crimson