Let’s Take a Walk

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...

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...

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 invi...

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 fun...

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 inte...

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 architectu...

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 condi...

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.

In this recording from 1998, Charlie Feld reflects on why high-performance IT is really a team sport. He talks about building shared values, rewarding the right behaviors, and focusing on quality instead of “just shipping it.” Charlie also shares how pattern recognition, not perfectionism, is what truly defines strong leadership. It’s a timeless reminder of what great teams are built on.

In this reflection from The Feld Group Institute archives, Charlie Feld shares his timeless perspective on technology as a digital fabric woven through every part of business and life. Recorded in 2021, his words about AI and the “augmentation of the human spirit” feel even more relevant today. We revisit Charlie’s message and reflect on how, four years later, his vision of technology amplifying h...

Legacy systems are expensive, slow, and inflexible, but AI is rewriting the modernization playbook. In this episode, Charlie talks with Nitin Rakesh (CEO of Mphasis) and Mike Childress (TFGI Affiliate and seasoned CTO), who explore how enterprises can transform core systems in months, not years, by combining AI-powered tools with serious engineering discipline. A must-listen for leaders tackling l...

In this clip from 2021, J.R. Jesson explores the distinction between an “organization at rest” and an “organization in motion.” His insights on structure, alignment, and empowered execution remain as relevant today as we continue to navigate the creation of cross-functional teams, the adoption of DevOps, and driving organizational flow. Learn more about J.R. here .

Michael Simmons, VP of Information Security at Ulta Beauty, talks with Sarah Bird, Microsoft’s Chief Product Officer for Responsible AI, about how AI, security, and trust intersect. Sarah shares Microsoft’s approach to safe deployment and real-world examples of balancing innovation with responsibility. This episode is packed with insights for anyone exploring or expanding their AI journey.   Learn...

As we enter September and the back-to-school season, it’s the perfect time to reexamine our Masterclass video series, Demystifying Digital Transformation , and explore how the series can be used to engage with your gamechangers and business partners. In this episode, we join Kenny Feld to expand on a powerful three-minute clip on the importance of layered architecture, and get into what it really...

George Finney joins the conversation to unpack the principles and practice of Zero Trust cybersecurity. The discussion explores the strategy’s origins, practical implementation, and the importance of protecting the “surface” rather than the “perimeter.” George shares insights from his books, stories of real-world breaches, and lessons from high-profile incidents. The conversation also addresses to...

AI is transforming the workforce: automating tasks, creating new roles, and challenging leaders to rethink how people and technology work together. In this episode, our panel of Jon Feld, Russell Villemez, Mike Childress, and Charlie Feld explores real-world applications and how to harness AI for both efficiency and value creation.

What if taking time off actually made your team more productive? In this episode, Brittany Butcher sits down with Charlie Feld to explore the power of work-life balance, and how simple shifts in leadership mindset can lead to big gains in health, engagement, and performance. Charlie shares real-world stories from his time at PepsiCo in the 1980s, where reflection and rest became a strategic advant...

Enterprise Architecture (EA) is critical to bridging business and IT, but getting buy-in across the organization is no easy task. In this episode, Russell Villemez and Jon Feld explore what it takes to sell EA internally, not just implement it. They unpack strategies for engaging executives, business leaders, and IT teams, while offering practical tips like simplifying the message, preparing metri...

This episode explores why digital transformations often fail, and how stronger business engagement can turn the tide. Jon highlights that companies with engaged business teams are 60% more likely to succeed. David Trent of Canfor and Hakan Yaren of KWE & APL Logistics share practical strategies from their own organizations, including how prioritizing uptime led to tangible results and how alig...

Charlie Feld and J.R. Jesson dive into the real-world challenges of scaling agile across large organizations. They highlight the power of dynamic, cross-functional teams and the critical role of operating models in enabling agility and collaboration. The conversation covers the balance between virtual and in-person work, the importance of cultural alignment, and how clear norms and digital tools c...

Join Jon Feld as he leads a dynamic Feld Group Institute Community Call with seasoned experts Mike Childress, Brent Browning, and Stan Alexander. Together, they unpack how EA becomes a game changer in business transformation, bridging today’s agile demands with tomorrow’s strategic vision. Hear their candid insights on avoiding the pitfalls, pacing EA adoption, and turning architecture into a true...

Jon and Charlie Feld take us deeper into the tried and true playbook for setting and selling the agenda for change. Together with the Community, they unpack the thinking, stories, and strategy behind establishing the WHY, WHAT, HOW, and WHO. They share practical ideas and discuss the real impact that today’s economic volatility is having on our organizations and decision-making.

In this episode, we dive into the evolving challenges and opportunities of leadership in a rapidly changing, remote-first world. Charlie is joined by Jeff Roemer, Feld Group Institute Affiliate and retired FedEx VP. Charlie and Jeff explore the critical role of effective time management, the importance of building strong CFO partnerships, and strategies for maintaining employee engagement across g...

In this episode, Charlie shares the proven Blind Spot playbook that has helped organizations across industries successfully navigate transformation. Whether you’re starting fresh or looking to accelerate an existing effort, this framework will help you align your team around a clear vision and a compelling case for change.  This episode is structured into four parts: The WHY – Understanding the ur...

Charlie is joined by Dottie Berry, former FedEx VP of IT Strategy, Planning, and Analysis , and Chris Winton, current SVP of Human Resources at Comcast and former Chief of People at FedEx. During this conversation they dive into the evolution of company culture at FedEx and beyond. They explore the role of leadership, talent investment, and adapting HR strategies for the future workforce. Listen f...