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/