Wednesday - June 24th, 2026
Apple News
×

What can we help you find?

Open Menu
May 31st, 2026

Episode 280: Leadership in the Age of AI with Molly Rosen

  1. Episode 280: Leadership in the Age of AI with Molly Rosen Darrin Peppard 33:37

What does leadership look like when the world is changing faster than ever before?

In this episode of the Leaning Into Leadership podcast, Dr. Darrin Peppard sits down with Molly Rosen, Co-CEO of ProjectNext Leadership, for a powerful conversation about leadership transitions, succession development, organizational agility, and the growing impact of AI on leadership and workplace culture.

Molly works with leaders across industries including tech, biotech, and Entertainment, helping organizations prepare leaders for critical next-level roles. Together, Darrin and Molly explore why the skills that make someone successful in one role often do not transfer automatically into leadership — and why emotional intelligence, communication, humility, and adaptability matter now more than ever.

The conversation dives into:

  • The transition from “player” to “coach” leadership
  • Why many leaders struggle to let go of their previous role
  • The dangers of over-relying on technical expertise
  • Succession development and building leadership pipelines
  • How AI is reshaping organizations and leadership expectations
  • The importance of organizational agility
  • Why leaders must communicate vision without pretending to have all the answers
  • “Sketch-based advocacy” and collaborative leadership
  • The role of empathy and emotional intelligence during uncertainty and change
  • Why leadership today is more about building teams than directing them

Molly also shares her own leadership Growth journey and the importance of prioritization and sequencing ideas as a leader.

This episode is a must-listen for school leaders, organizational leaders, and anyone navigating leadership in rapidly changing environments.

About Molly Rosen

Molly Rosen is Co-CEO of ProjectNext Leadership. She has worked with leaders in tech, entertainment, and biotech for over 20 years as an executive coach, facilitator, and consultant developing innovative talent systems.

Her clients have included organizations such as Pixar, Airbnb, DocuSign, and Samsung, where she has helped leaders prepare for critical transitions and organizational change.

Molly previously held leadership roles with BlessingWhite and Ninth House Network and holds an MBA from UCLA Anderson and a BA from UC Berkeley.

Connect with Molly Rosen

LinkedIn: https://www.linkedin.com/in/mollyrosen/

Website: https://www.projectnextleadership.com/

Sponsor Spotlight:

This episode is sponsored by HeyTutor.

HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems.

Learn more here: HeyTutor.com

Darrin Peppard Dr. Darrin Peppard

Dr. Darrin Peppard is an author, leadership coach, consultant, and speaker focused on organizational culture and climate, and growing emerging leaders. Darrin is the best-selling author of the book Road to Awesome, and is the host of the Leaning into Leadership podcast. As a ‘recovering high school principal’, Darrin shares strategies and lessons learned from 26 years in public education to help leaders gain clarity, find joy in their work, and walk in their purpose.