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 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.

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 human potential has become a reality.

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 legacy debt.   Learn more about Nitin here. Learn more about Mike here.

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 more about Michael here. Learn more about Sarah here.

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 means for leaders to be change-ready. We’ll talk about why architecture isn’t just for tech folks, how loosely coupled systems create speed and agility, the role of a durable digital brain in unifying data, and why the real promise of AI depends on getting the foundation right. This episode demonstrates how these ideas and videos can spark meaningful conversations with your teams, gamechangers, and business partners. 

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 today’s most pressing challenges: securing AI systems, mitigating vulnerabilities in legacy systems, and preparing business leaders to engage proactively in cybersecurity. A must-listen for leaders seeking to build resilience in a world where trust is no longer a given. Learn more about George here.

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 advantage. 

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 metrics, and anticipating objections. The conversation also explores EA's evolving role in AI and risk management, as well as how establishing a shared language across functions can drive modernization and innovation. Whether you’re just starting an EA practice or trying to reinvigorate one, this episode offers insights to help you align stakeholders and create lasting momentum.   Learn more about Jon here.  Learn more about Russell here. 

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 aligning capabilities to strategic goals builds trust and traction. The panel also discusses the value of operational excellence, the importance of cross-functional collaboration, and how to sustain strategic conversations with internal and external partners.

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 can support distributed teams. They also explore what it takes to build future-ready organizations with adaptable strategies, integrated enterprise architecture, and leadership grounded in trust, autonomy, and workforce development in an AI-driven world.   Learn more about J.R.’s career here. 

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 business enabler.   Learn more about the panelists here: Jon Feld Stan Alexander Brent Browning Mike Childress 

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 global teams. They share insights on fostering personal relationships to drive strategic alignment, navigating the complexities of remote work, and protecting teams from burnout in high-pressure environments. Join us as we unpack how to lead with clarity, connection, and purpose…no matter the chaos you face.  Learn more about Jeff's career here. 

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 urgent need for change and the forces driving transformation. The WHAT – Defining the critical business and technology shifts required to thrive in the digital era. The HOW – Crafting strategies to align the organization around a shared vision and executing the transformation—across processes, technology, people, financials, and governance. The WHO – Identifying the game changers within the organization—those who can lead the narrative and inspire action. Transformation isn’t just a buzzword. It’s a challenge, an opportunity, and a responsibility. It begins with asking the right questions and empowering the right people. 

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 for a deep dive into the intersection of culture, leadership, and people.   Learn more about their careers here:    Dottie Berry   Chris Winton 

Charlie is joined by Kenny Feld, Chief Transformation Officer, and the earliest member of the Feld Group. Kenny is a Feld Group Institute Affiliate who, in 2024, took a role as the Chief Transformation Officer with Associated Materials, a North American building products manufacturer and distributor.  Charlie and Kenny get into the complexities of business operations and the strategies needed to scale successfully. Drawing from real-world experiences, including insights from our favorite Herman Lay and the founder model, they explore how understanding a business’s core WHY can lead to better decision-making.  Join us for valuable insights on business strategy, technology leadership, and organizational growth! Learn more about Kenny's career here. 

In this live recording with our Community, we dive deep into leadership, technology, and the art of storytelling with two seasoned leaders—Charlie and Rob Carter. Rob, who spent 25 years as CIO at FedEx, has been instrumental in driving innovation and shaping the future of tech leadership. We’ll uncover how great leaders adapt, inspire, and drive change. Plus, we’ll discuss the crucial role of agility in staying relevant in today’s fast-paced world. Whether you're a seasoned executive or an emerging leader, get ready for insights that will transform the way you think about leadership, technology, and the future of our work. Learn more about Rob here: https://www.linkedin.com/in/robcarter1/

Charlie sits down with Mike Childress, an Affiliate of the Feld Group Institute and a seasoned IT leader. As Chief Technology Officer, Mike has played a pivotal role in designing and deploying IT solutions across various sectors, most recently in Transportation. Charlie and Mike explore the value of building strong connections with teams by walking the halls and emphasize the importance of alignment, trust, and approachability in today’s hybrid work environment. Find out more about Mike's work and career here: https://www.linkedin.com/in/mike-childress/ 

Charlie is joined by David Trent, Senior Vice President of Business Development at Canfor. David oversees mergers and acquisitions, growth strategies, sustainability initiatives, and technology. Canfor, a global leader in the forest products industry, is one of the world’s largest producers of sustainable lumber, pulp, and paper. Together, Charlie and David explore lessons learned across industries and discuss the pressing need for businesses to adapt to challenges like supply chain disruptions, labor shortages, geopolitical conflicts, and regulatory changes. David’s unique blend of business acumen and technical expertise provides a blueprint for navigating these complexities and securing long-term success. Find out more about David and his career: https://www.linkedin.com/in/davidmtrent/ 

Charlie is joined by John Jacobi, CIO, and Shannon Okinaka, CFO, of Hawaiian Airlines—Hawaii's largest and longest-serving airline. Known for leading all U.S. carriers in on-time performance since 2004, Hawaiian Airlines recently entered a new chapter as part of Alaska Airlines following a completed acquisition last fall. The two airlines are now working toward integrating under a single FAA operating certificate, a process filled with complexities. John and Shannon bring a unique perspective shaped by Hawaiian culture and an exceptional partnership between technology and finance—an alignment that may be key to navigating transformation successfully. Learn more about John and Shannon's journeys here: https://www.linkedin.com/in/johnjacobi/ https://www.linkedin.com/in/shannon-okinaka-2a060139/  

Welcome to Let’s Take a Walk, brought to you by the Feld Group Institute. We are excited to introduce this new podcast series where we’ll dive into insightful conversations covering strategic blind spots and showcasing leadership insights that inspire growth and transformation. Our goal is to proactively share our Community’s collective experience –not only with each other but also with your broader networks of colleagues and business partners. Here’s Charlie Feld with a message for the Feld Group Institute Community as we enter this next chapter.