Let’s Take a Walk

Breaking Free from Legacy: AI’s Role in Enterprise Modernization with Nitin Rakesh and Mike Childress

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.

Still Relevant Today: J.R. Jesson on Organizational Motion

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.

Responsible AI in Practice: Microsoft’s Sarah Bird on Trust, Security, and the Future of AI

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.

Back to School with the Technology Model: Are You Change Ready?

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. 

Zero Trust in an AI World: Insights with George Finney

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 and the Future of Work: Transforming Tasks, Roles, and Value

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.

From Burnout to Breakthrough: A Healthier Way to Lead

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. 

Selling Enterprise Architecture: Aligning Strategy, Overcoming Resistance, and Enabling Innovation

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. 

Business Engagement: The Key to Transformation Success

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.

Beyond Agile: Reimagining Teams, Leadership, and Enterprise Architecture at Scale

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.