14. Gen Z vs Gen X: Real Talk on Leadership, Respect & Communication

What happens when a Gen X CEO and a Gen Z CMO join forces to build something big? 

In this episode of B Student Podcast, host Betsy Gardner sits down with her collaborator and Chief Marketing Officer, Addison Cursey, for a real conversation on navigating multigenerational leadership in the modern workplace.
From decoding communication differences to wardrobe hacks that build credibility, this episode is packed with funny, vulnerable, and incredibly practical insight into how professionals from different generations can better understand, respect, and elevate each other.

Topics include:

• How to read the room across generations
• Why “dressing old” might help your career
• What Gen Z and Boomers misunderstand about each other
• Practical tips for showing up with gravitas
• The power of wonder, curiosity, and failing together

Whether you're 24 or 54, this episode will shift the way you think about collaboration, leadership, and communication in a rapidly evolving work environment.Drop your favorite takeaway in the comments—and let us know how you’re bridging the generational gap at work.

Time Stamps:

• 00:00 – Welcome + Meet Addison Cursey
• 01:42 – Why Navigating Generations Matters Now
• 03:27 – Gen Z vs Gen X: How We Communicate Differently
• 06:10 – A Website Training Gone Wrong (and Right)
• 08:55 – Evergreen Resources vs Real-Time Support
• 11:33 – Wonder, Curiosity & Learning How to Ask Better
• 14:25 – Becoming “Translators” Across Generations
• 16:02 – How HBO’s Hacks Mirrors Our Working Relationship
• 18:37 – Managing Up (Starting with Mom!)
• 21:08 – Dressing the Part: “Dress Older” Strategy Explained
• 23:46 – Cheat Code: Ask What to Wear
• 26:09 – Stakeholder Perception & the Power of Clothing
• 28:33 – The New Professional: Stylish, Polished & Context-Aware
• 30:48 – Showing Up with Gravitas Without Losing Approachability
• 33:24 – Pantyhose, Politics, and the Panopticon
• 36:01 – Dressing Your Calendar & Why Consistency Matters
• 38:20 – Leadership Without a Title: Earning Trust Early
• 40:12 – Practical Tips to Build Trust Across Generations
• 41:30 – Closing Thoughts & What’s Coming Next

Watch now and drop a comment with the one word that describes your B-side.

Subscribe, rate, and share the B Student Podcast—because the B side of your story might just be the best part.

Connect with Addison Cursey:  https://www.linkedin.com/in/addison-cursey-mba-353344151/
Connect with Betsy Gardner: https://www.betsygardner.com/ 

Learn More about Winter Park Chamber of Commerce: https://www.winterpark.org/

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Podcast produced by Hi Hello Labs: https://www.hihellolabs.com/