23. Managing Up 101: Gen Z & Gen X Secrets to Fast-Track Trust

Authentic… or “plastic fantastic”? In this B-Student Podcast episode, Betsy sits down with CMO (and resident Gen Z/Millennial lens) Addison Cursey to unpack how to show up at work—without tanking your credibility. From email punctuation and dress codes to “managing up,” building trust, and navigating AI, this is a practical guide for early-career pros and the managers who lead them.

What you’ll learn:

• Authenticity vs. professionalism: where the line actually is
• The “costume party” problem of modern workplace culture
• Email tone, exclamation points, and the “gravitas gap”
• Dress codes (why pajamas/crop tops send the wrong signal)
• Managing up: reading your boss’s calendar, anticipating needs
• Fast-tracking trust: judgment, reliability, and asking for context
• Cross-generational collab: Gen Z × Gen X strengths, staying open
• Using AI as leverage (not a crutch)

Time Stamps:

• 00:00 — Welcome and setup
• 02:20 — Orlando Women’s Conference shoutout and theme of authenticity
• 05:05 — Five generations at work and the AI wrinkle
• 07:40 — Authentic vs “plastic fantastic”
• 10:15 — Dress code reality check: pajamas and crop tops
• 12:40 — Email tone and the exclamation point rule
• 15:10 — How Addy built trust fast and moved up
• 17:35 — “Be yourself” at work and the costume party metaphor
• 20:05 — First two weeks: listen before you speak
• 22:25 — Managing up 101
• 24:40 — Know your boss’s calendar and the “Betsy buffer”
• 27:05 — Coaching vs over-accommodating the team
• 29:20 — Tech fluency across generations
• 31:10 — Cross-gen relationships that build trust
• 33:00 — Key takeaways and your next steps
• 34:30 — Closing and call for questions

Have a question about cross-gen teamwork or the unwritten rules of work? Drop it in the comments and we might cover it next.

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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/