23. Managing Up 101: Gen Z & Gen X Secrets to Fast-Track Trust
15 October 2025

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

B Student Podcast

About
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 isThe “costume party” problem of modern workplace cultureEmail 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 needsFast-tracking trust: judgment, reliability, and asking for contextCross-generational collab: Gen Z × Gen X strengths, staying openUsing AI as leverage (not a crutch)
Time Stamps:
    00:00 — Welcome and setup02:20 — Orlando Women’s Conference shoutout and theme of authenticity05:05 — Five generations at work and the AI wrinkle07:40 — Authentic vs “plastic fantastic”10:15 — Dress code reality check: pajamas and crop tops12:40 — Email tone and the exclamation point rule15:10 — How Addy built trust fast and moved up17:35 — “Be yourself” at work and the costume party metaphor20:05 — First two weeks: listen before you speak22:25 — Managing up 10124:40 — Know your boss’s calendar and the “Betsy buffer”27:05 — Coaching vs over-accommodating the team29:20 — Tech fluency across generations31:10 — Cross-gen relationships that build trust33:00 — Key takeaways and your next steps34:30 — 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/