Transformation is not an IT project.

It’s a fundamental shift in how a business operates.

In this short episode, Charlie Feld explains: • What makes a true transformation different from incremental change • Why most companies struggle to execute • How legacy systems and “veneers” hold organizations back • The risk of moving too fast or too slow • Where leaders should actually start

The takeaway is simple:

Technology may be the catalyst, but the real work of transformation happens in the organization.

In this episode, Charlie Feld and Brittany Butcher explore what USA Men’s Hockey Coach Mike Sullivan’s leadership philosophy teaches us about leading technology transformation. His approach centers on simplicity, clear roles, accountability without fear, and cultural consistency.

When organizations face pressure, uncertainty, and high expectations, transformation can feel like playing defense all game long.

The difference between surviving and winning is the environment leaders create.

In this mini episode of Let’s Take a Walk, we revisit a clip from a conversation Charlie had with Rob Carter where they explore one of the most underrated leadership capabilities: storytelling.

Drawing from decades of experience at FedEx and beyond, Rob shares how great leaders use analogies and shared reference points to make complex technology understandable. Not to “sell” an idea, but to invite the business into it. From dominant design to digital twins, this conversation illustrates why clarity, not complexity, is what ultimately drives alignment and momentum.

A short, practical listen for leaders navigating transformation who want their ideas to land. And stick.

Learn more about Rob here: https://www.linkedin.com/in/robcarter1/

In this episode of Let’s Take a Walk, Charlie Feld shares a defining story from early in his career. Facing unexpected complexity and early failure during a major railroad transformation, Charlie realized that vision and strategy alone were not enough. What changed everything was finding the right people, particularly one architect who helped him see systems, organizations, and leadership in a fundamentally new way. That moment became the foundation for the models and patterns that later shaped decades of successful transformations.

This conversation is a reflection on recognizing blind spots, building teams with complementary strengths, and understanding why leadership and culture matter more than any framework. For anyone navigating change and wondering how to move forward, this episode is an invitation to pause, reflect, and find your Stan.

Learn more about the original Gamechanger, Stan Alexander, here: https://www.linkedin.com/in/stan-alexander-a83a745/

Charlie sits down with longtime friend and former FedEx executive, Ken Spangler, to explore what the AI era truly means for enterprises and leaders. Drawing on decades of experience running technology and operations at a massive global scale, Ken reframes AI not as a technology challenge, but as a productivity and adaptability imperative. Together, they discuss the shift from IT enablement to integration and transformation, the rise of innovation at the edge, and why human systems remain the long pole in meaningful change.

Learn more about Ken here.

In this episode of Let’s Take a Walk, Charlie Feld is joined by John Rossman, former Amazon executive and author of Big Bet Leadership, for a wide-ranging conversation on what it really takes to lead transformation in the AI era. Together, they explore why most large transformations fail, how leadership for operational excellence differs from leadership for high-risk innovation, and why architecture, storytelling, and long-term stewardship matter more than ever. Drawing on lessons from decades of CIO experience, this conversation challenges leaders to stop waiting, start experimenting, and build organizations designed for change.

https://johnrossman.com/

https://www.linkedin.com/in/john-rossman/

J.R. Jesson hosts a conversation with Roche’s Hemerson Paes about what it really takes to make work visible inside a modern organization. Hemerson shares lessons from Roche and the broader Feld Group community about the realities of teams in motion, the limits of traditional org charts, and why clarity and connectedness matter more than ever. Together, they explore how leaders can create the conditions for alignment, flow, and meaningful progress.

Learn more about J.R. here.

Learn more about Hemerson here.

In this Thanksgiving week episode, we take a quick walk through how gratitude actually shows up in real leadership and team culture. We reflect on gratitude, teamwork, and the long arc of real transformation. A short listen for a busy season.