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.
🎙️ 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.
