Bridging Generational Leadership

This session continues the generational leadership conversation we began in October, deepening our exploration of how leaders work across differences while preparing for what comes next.

Today’s organizations are shaped by multiple generations with distinct communication styles, expectations, and approaches to leadership. When left unexamined, those differences can create friction instead of progress.

This highly interactive session will include a hosted lunch while Senior Fellows engage in conversation, learning, and connection. Facilitators Katie McCleary and Nicholas Miller will guide participants through a dynamic exploration of generational leadership using Sticking Points by Hayden Shaw as a foundational framework.

Senior Fellows will identify and unpack common “sticking points” that arise across generations and examine how they show up in real workplace dynamics.

The session will also include a panel discussion, creating space for honest dialogue around leadership transition, legacy, and how we intentionally extend leadership across generations.

By the end of the session, Senior Fellows will walk away with:

• Greater awareness of how generational experiences shape leadership
• Practical insight into common generational sticking points
• Strategies for creating space for the next generation of leaders
• A renewed capacity to lead transitions with empathy and shared responsibility