104: Boomers to Gen Z: The Leadership Skills Every Manager Needs Now w/ Gabby Rosely

If you’ve ever struggled to understand why different generations communicate, work, and clash so differently, this episode will give you a new lens on leadership.

In this conversation, Sean Patton sits down with Gabby Rosely, keynote speaker, leadership trainer, and host of The Gabby Rosely Podcast. Gabby stepped into leadership at just 21 years old, managing boomers, Gen X, millennials, and Gen Z simultaneously—an experience that shaped her expertise in multi-generational communication and leadership.

Together, Sean and Gabby unpack what it really takes to build trust, accountability, and strong culture across age groups. They explore the challenges of moving from individual performance to leadership, the difference between being nice and being kind as a leader, and how generational blind spots can quietly derail teams.

This episode is a must-listen for leaders, managers, and entrepreneurs who want to communicate better, retain top talent, and create workplaces where every generation can thrive.

Chapters

00:00 – Why Generations Clash at Work
02:00 – Stepping Into Leadership at 21
04:30 – From Individual Performer to Team Leader
07:30 – Leading by Example vs. Taking Charge
10:30 – Kind vs. Nice Leadership
14:00 – Blind Spots and Why Leaders Need Coaches
18:30 – Developing Leaders, Not Just Performers
22:30 – Understanding Boomers, Gen X, Millennials, and Gen Z
27:00 – Keeping Gen Z Engaged at Work
32:00 – Vision, Alignment, and Team Buy-In
35:30 – Leveraging Multi-Generational Strengths
40:00 – Culture Shifts and the Search for Structure
45:00 – Where to Connect with Gabby Rosely
Guest Links

Gabby Rosely – LinkedIn:   / gabbyrosely  

Gabby Rosely Podcast: https://podcasts.apple.com/us/podcast...
https://open.spotify.com/show/26HaB2h...
YouTube (Speaking Videos):    / @gabbyrosely