Why do so many well-intended change initiatives fail even when the strategy is sound? In this episode, we examine why leadership, not technology or structure, is the decisive factor in whether change actually takes hold.

In this conversation, Sim Sitkin sits down with Richard Freishtat to explore how executive education can serve as a powerful lever for both individual growth and organizational transformation. Drawing on decades of experience designing leadership programs, Freishtat explains why the most persistent challenge organizations face is not innovation or systems, but people, behaviors, and culture.

Together, they unpack how executive education can help leaders navigate constant and accelerating change by aligning individual development with enterprise-wide priorities. The discussion highlights the importance of creating conditions for learning, embracing feedback as a catalyst for growth, and building trust that can withstand imperfection. They also examine why coaching and feedback are essential to making leadership development “stick,” and why academically grounded frameworks, such as the Six Domains of Leadership, provide leaders with durable guidance amid uncertainty. Ultimately, the episode reframes leadership as the daily work of enabling change, not managing it from the top.

About Richard Freishtat

Richard Freishtat is Associate Dean for Executive Education at Duke University Fuqua School of Business, where he has guided thousands of leaders through periods of growth and transition. His work focuses on designing executive education programs that integrate academic rigor with practical impact to support organizational change and leadership development.

Key Leadership Takeaways

•Organizational change fails when only individuals change; transformation must be reinforced across the system.

•Leadership today is less about expertise and more about creating the conditions for learning, trust, and experimentation.

•Executive education delivers the greatest impact when individual development is aligned with organizational priorities.

•Feedback and coaching are essential for making leadership behaviors stick beyond the classroom.

•Academically grounded frameworks help leaders navigate rapid change without chasing every new trend.

Timestamps

0:00 – Trailer / Episode Preview

1:00 – Podcast Intro and Show Overview

2:00 – Introduction of Richard Freishtat

3:00 – Why the real challenge of change is people, not technology

8:30 – Individual vs. organizational leadership development

15:00 – Culture, trust, and the “snapback” effect of failed change

23:00 – Creating conditions for learning and innovation

31:00 – Why executive education matters and when organizations invest

41:00 – The role of feedback and coaching in sustaining change

48:00 – Leading in an era of constant, accelerating change

50:30 – Closing reflections and final thoughts on leadership