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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Ever wondered why your boss, your mentor, or your Gen Z colleague just doesn’t seem to “get” how you work? Or why feedback that fires up one generation can shut down another?
Chris and Lily sit down with Gabby Rosely - former competitive swimmer turned entrepreneur, corporate leader and now multigenerational teams expert - to unpack the real reasons behind generational friction at work.
Gabby has managed teams spanning Boomers to Gen Z while still in her twenties, and she’s here to share what actually helps us connect, communicate, and collaborate across age divides.
You’ll learn:
- The surprising historical forces that shaped each generation’s work style
- Why “Engage-Discuss” vs. “Command-Obey” is the key model to understanding generational differences
- How different generations view and want to receive feedback - and how to adapt when it’s not your style
- Whether gender plays a role in these workplace dynamics
- The story behind Gabby’s 77-year-old mentee - and her personal motto, “Say yes before you’re ready!”
Whether you’re managing, mentoring, or just trying to get along in a multigenerational team, listen in and you’ll discover how to bridge the gap - and build a workplace where every generation thrives.
Hit play now and decode the generations with us.
3.10 Intro to Gabby
4.20 Gabby’s story
6.53 Historical influences shaping each generation (7.33 Boomers; 9.13 Gen X; 12.04 Millennials; 13.55 Gen Z)
12.34 Engage-Discuss vs Command-Obey
15.49 How the generations connect and motivate people at work (16.12 Boomers; 17.20 Gen X; 19.45 Millennials; 20.40 Gen Z)
21.18 Different generational views on feedback
23.06 How to avoid getting it wrong with other generations
27.27 Is there a gendered element to these challenges?
32.03 How each generation wants to receive feedback (32.15 Gen Z; 32.54 Millennials; 33.16 Gen X; 33.56 Boomers)
34.30 How to respond if feedback doesn’t meet your preferences
36.08 Gabby’s 77-year-old mentee
38.55 Gabby’s motto - “Say yes before you’re ready!”
41.26 Walking away and moving to Costa Rica
46.48 Gabby’s programs and how you can connect to learn more
49.00 Our key takeaways
Connect with Gabby Rosely:
https://www.linkedin.com/in/gabbyrosely/
Send us a voice message on Speakpipe!
https://www.speakpipe.com/thegenxzexchange
Connect with us:
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