What turns a promising team into a durable company? John Connors—former Microsoft controller, CIO, CFO, and long-time VC—joins us to dive into the mechanics that actually move the needle: recruiting exceptional people, making clear calls under pressure, and scaling only after the signals are real. From a Montana upbringing marked by hard work on farms and railroads to high-stakes meetings with Bill Gates and Steve Ballmer, John shows how resilience and curiosity become a leader’s edge.

For decision-makers dealing with high-stakes growth and for any leader who’s ever felt alone in tough calls, John opens the door to the Microsoft engine room during hypergrowth: consolidating onto a single SAP instance, building analytics muscle, and transforming IT from a cost center into a strategic proving ground. The dogfooding era comes alive—why no enterprise release shipped without IT’s signoff—and how that cultural shift became peer-powered disruption that reduced downtime, boosted credibility, and gave sales a living case study for enterprise computing.

We also examine leadership tone in a culture obsessed with lowlights over highlights, pointing to Bob Herbold’s calm predictability as a model for keeping the room cool while standards stay high. Sometimes, the most effective call is “not your problem”—focusing leaders where they can make the greatest impact.

Then we get practical about venture and entrepreneurship. John explains why overinvesting early is a trap, how to incubate cheaply until product-market fit shows up, and why timing—catching the right wave—can outweigh raw horsepower. He breaks down the harsh math of VC, the compassion required when it’s time to stop funding the dream, and the three founder traits that matter most: recruit A players, be relentlessly optimistic, and get comfortable being unpopular.

For anyone ready to challenge their comfort zone in venture, corporate leadership, or team-building, this conversation is a masterclass in clarity, courage, and compounding judgment. Real leaders. Real stories. Real action.

If it resonates, follow the show, share it with a builder who needs it today, and leave a review to help more people find these conversations.

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Pull up a chair. There’s always room for your seat at the table.

What if the most valuable seconds of your life aren’t the longest ones—but the ones that ripple the farthest? In this episode, we sit down with Olympian and design thinking expert John Coyle to rethink how performance, memory, and time actually work, and how a few well-designed moments can reshape a career, a team, or a family.

For decision-makers dealing with impossible trade-offs, and for any leader who’s ever felt alone in tough calls, John shares what happens when you stop trying to “fix weaknesses” and instead “run toward the roar.” From Stanford’s product design program to the Olympic Training Center, he discovered that true design thinking means redefining the problem, racing your strengths, and embracing a question-driven approach. That shift not only saved his career but also became a blueprint for business: reorganize teams by talent, detach from first ideas, and commit only once reality proves the fit.

Along the way, we explore the six lenses that real leaders use to unlock outsized outcomes—showing why strengths are specific, weaknesses are broad, and why “not your problem” can actually be a catalyst for growth. The result is peer-powered disruption: a fresh model of leadership built on collaboration, clarity, and courage.

Then we take on time itself. Drawing on neuroscience, John explains why memory is the real currency of time and how to “buy” more of it. The formula is practical and bold: stack risk and uncertainty, uniqueness, emotional intensity, beauty, and flow to wake the amygdala and write thicker memories. From running into storms with your kid, to designing surprise rites of passage, to building travel itineraries that leave room for serendipity—you’ll learn how to create moments that feel bigger and last longer.

For anyone ready to challenge their comfort zone and perform better under pressure, this conversation delivers both mindset and method. Real leaders. Real stories. Real action.

If you’re ready to stop counting hours and start crafting experiences that matter, tune in, subscribe, share with a friend who needs a nudge toward their strengths, and leave a review with one moment you’ll design this week.

🎙️ Enjoyed this conversation?
Subscribe to Your Seat at the Table for more candid discussions on leadership, growth, and the real stories behind the decisions that shape great organizations.

💬 We'd love to hear from you! Share your thoughts in the comments — or let us know what topics you'd like us to explore next.

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👉 Listen on Apple Podcasts & Spotify: https://podcasts.apple.com/podcast/id1826002539
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👉 Connect with us:
https://www.linkedin.com/in/gmichaelmaddock/
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Pull up a chair. There’s always room for your seat at the table.

Martha McSally's life story reads like an action-packed novel—from losing her father at 12 to becoming America's first female fighter pilot in combat to serving as a U.S. Senator. But beneath these remarkable achievements lies a profound journey of self-discovery that offers wisdom for anyone struggling with identity, purpose, and leadership.

For anyone ready to challenge their comfort zone or confront what’s holding them back, this conversation is an invitation to run toward the roar—to face the hard stuff head-on with courage and clarity.

Martha reflects on the sudden loss of her father and his final words to “make him proud”—a mission that propelled her forward but eventually became a weight she had to release. With rare candor, she reveals how grief, grit, and rebellion shaped her path to the Air Force Academy, where she was told women were legally barred from becoming fighter pilots. Her reaction: “That’s exactly what I’m going to do.”

Martha’s approach to leadership—whether commanding fighter missions or navigating Washington’s political turbulence—centers on authenticity, resilience, and mission-focus. She doesn’t sugarcoat her Senate experience, describing Congress as “a different combat zone” where she fought to lead with integrity despite a frustrating environment. “It was one of the highest honors of my life to be a U.S. Senator... and also the most frustrating thing I’ve done in my life.”

Through the six lenses of identity, courage, purpose, leadership, failure, and freedom, Martha challenges leaders to strip away external expectations and get clear on who they really are. Her “I am” statements—unbreakable, courageous, generous—aren’t just affirmations, they’re anchors for decision-making in uncertain times.

For leaders navigating post-pandemic complexities, Martha offers straight talk: your team has to “show up and work,” but leadership today also means creating spaces where creativity and sustainability coexist. She draws a powerful distinction between “whatever it takes” seasons and “good enough” rhythms—an essential mindset shift for long-term impact.

Real leaders. Real stories. Real action. Martha’s journey is more than inspirational—it’s instructional. Her story proves that the most effective leadership isn’t about status or control; it’s about showing up with clarity, conviction, and compassion.

Ready to explore your own edge? Connect with Martha through her adventure experiences or speaking engagements. Visit her website to discover how her unique blend of military discipline, political insight, and soul-deep authenticity can help transform your leadership and your life.

🎙️ Enjoyed this conversation?
Subscribe to Your Seat at the Table for more candid discussions on leadership, growth, and the real stories behind the decisions that shape great organizations.

💬 We'd love to hear from you! Share your thoughts in the comments — or let us know what topics you'd like us to explore next.

👉 Subscribe: https://www.youtube.com/@YourSeatatTheTablePodcast
👉 Listen on Apple Podcasts & Spotify: https://podcasts.apple.com/podcast/id1826002539
https://open.spotify.com/show/0fDDb1gvrvsttm4nInRL8Y

👉 Connect with us:
https://www.linkedin.com/in/gmichaelmaddock/
https://www.linkedin.com/in/john-tobin-a54225/
https://flourishadvisoryboards.com/
https://www.mike-maddock.com/

Pull up a chair. There’s always room for your seat at the table.