Authenticity vs. Professionalism: Navigating Generational Expectations in the Modern Workplace

How Young Professionals Can Build Trust, Manage Up, and Decode Unwritten Rules in Multigenerational Offices

The workplace is evolving fast -- with five generations under one roof and a constant stream of technological change, including AI, it’s never been more nuanced or complicated to thrive professionally. In this episode of the B Student podcast, host Betsy Gardner (Gen X) sits down with Addison Cursey (Gen Z/Millennial), her Chief Marketing Officer and in-house “generational translator.” Together, they unpack what authenticity really means at work, why it matters (and when it can backfire), and how early-career professionals can decode unwritten rules to accelerate their growth.

The Authenticity Debate -- Where “Come As You Are” Meets “Costume Party”

Authenticity is thrown around in job postings and onboarding sessions -- “bring your whole self to work,” “show up authentically.” But what does that look like in reality? Addison references Jodi-Ann Burey’s TED Talk, highlighting the trap of vague invitations: “Come as you are!” only to walk into an office operating as a “costume party,” with hidden expectations.

As Betsy and Addison discuss, young people today are encouraged to embrace their uniqueness, but the professional stage still demands a certain costume -- “wear pajamas or a crop top if you want,” Betsy jokes, “but don’t expect to be taken seriously.” The stakes are real: promotions, income and opportunities hinge on whether you telegraph judgment and trustworthiness to those in decision-making roles.

Decoding Unwritten Rules -- Listen, Learn, and Model Up

The “hidden curriculum” of work is alive and well. While official orientation manuals might outline dress codes and meeting etiquette, the true game of career advancement plays out through unwritten rules: when to speak, how to communicate, how much enthusiasm to show, and whom to model.

Addison advises interns and new hires to spend their first two weeks observing, listening, and absorbing the norms -- “You might have a right to be in the room, but you don’t have a right to speak yet.” She cautions young professionals to avoid over-identifying with senior staff who enjoy more leeway; instead, look to the next rung on the ladder (coordinator, associate), and emulate their choices. This careful approach signals readiness and respect for professional boundaries, ultimately accelerating trust-building.

Building Trust Across Generational Lines

Trust is the currency of promotion -- and nothing erodes it faster than “making your manager nervous,” as Betsy puts it. What does earning trust look like?

Show good judgment: Avoid constant complaints, demonstrate reliability, and ask for help strategically, not habitually.

Understand the stakes: Realize that signal blunders (too many exclamation points, overly casual attire) may bar you from leadership tracks, regardless of your competency.

Close the gravitas gap: Adjust your communication style to match professional standards -- if you’re emailing a Gen X exec, limit your exclamation points!

Addison credits much of her rapid rise (from coordinator to CMO in three years) to learning the unwritten rules, modeling responsible colleagues, and actively seeking mentorship and coaching.

The Power of Managing Up -- and How to Do It

Managing up is more than anticipating your manager’s needs; it’s about intentionally partnering with those you report to for mutual success. Addison’s hacks include knowing your boss’s calendar, understanding their pressure points, and tuning your communication to their preferences (Betsy loves data-driven spreadsheets, not chit-chat). Practical insights -- like the “Betsy Buffer” for meeting timings -- show Addison’s commitment to seamless collaboration.

This practice isn’t about flattery or subservience; it’s about making yourself indispensable and clearing a fast track to responsibility and advancement.

Conclusion: Stay Open, Stay Curious -- But Read the Room

The ultimate takeaway? It’s possible to be authentic without sabotaging your potential. Betsy urges older professionals to coach, not complain about younger colleagues. Addison encourages younger professionals to remain open to learning from other generations, not just their own. The most successful teams -- and careers -- are built on trust, flexibility and intentionality.

The B Student podcast was launched in 2025 by Winter Park Chamber President and CEO Betsy Gardner to get to know the "B" side of some of the most fascinating people in our network, hear inspirational stories and learn strategies for success in your business.