Generational FLUENCY Masterclass

Bridge the Gap. Lead Across Generations.

A practical masterclass to help you speak the language of every generation in your workplace - from Boomers to Gen Z (and beyond).

Who Is This Masterclass For ?

Not every workplace challenge is about skill.

Sometimes it’s about speaking across generations—and that’s where the friction shows up.

This masterclass is designed for leaders who need to turn “us vs. them” into we.

  • HR Professionals & People Leaders juggling Boomers, Gen X, Millennials, and Gen Z under one roof.

  • Executives & Team Leads who feel the strain of misalignment, misunderstandings, and stalled collaboration.

  • Family Business Leaders navigating succession, legacy, and generational clashes at the decision-making table.

  • Founders & Decision-Makers tired of hearing “they don’t get it”—and ready to actually solve it.

Learn how to translate across age groups, align diverse perspectives, and build a culture where every generation contributes - and no one feels left out.

Powered By

Sider Road : A Business Transformation Company

Bridge Builders is a 3-month, small-group masterclass built to unlock generational fluency masterclass—the skill of understanding, leading, and communicating across today’s five (sometimes six) workplace generations.

Whether you’re :

  • Onboarding Gen Z hires

  • Engaging Millennial talent

  • Mentoring Gen X professionals

  • Navigating Boomer expectations

  • Or honoring Traditionalist values

…this program equips you to decode unspoken tensions and turn them into collaboration that actually works.

Small group. High trust. Real transformation.

Meet Your Strategic Guide

Jocelyn Greenky Underwood, MBA Family Business Strategist

Business Transformation Expert & Family Business Specialist

  • 15+ years specializing in family business dynamics

  • MBA in Strategic Management

  • Trained 1,500+ male partners in strategic support

  • Author of "Behind Every Great Business: The Strategic Male Partner"

  • Featured expert on family business podcasts and conferences

Why Trust Jocelyn : She understands communication styles and has developed frameworks that work with your natural problem-solving instincts, not against them. Her approach is direct, practical, and results-focused.

FEATURED IN

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Who Should Join?

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The Perks

Get exclusive access to proven frameworks that most family businesses spend decades trying to figure out on their own.

  • Confidential peer network of families facing similar transition challenges

  • Customized strategies developed specifically for your family's unique dynamics

  • Direct access to expert guidance between sessions for urgent situations

  • Proven frameworks that have successfully guided 500+ family business transitions

  • Lifetime access to updated family business resources and future program discounts

  • HR professionals and People Leaders navigating the complexity of multigenerational teams

  • Executives and team leads struggling with generational misalignment and communication gaps

  • Family business leaders facing succession challenges and internal breakdowns

  • Founders and decision-makers tired of hearing “they just don’t get it” — and ready to fix that

Whether you’re managing Boomers, Gen X, Millennials, or Gen Z — Jocelyn helps you bridge the gap, reduce friction, and actually get people talking (and working) together.

Voices From Customers

Finally, my team gets each other

I used to feel like every meeting was a translation battle—Boomers rolling their eyes at Gen Z, Millennials frustrated with Gen X. This program gave us a common language. Productivity is up, and so is trust..

Maria S., HR Director

The succession conversations shifted overnight.

In our family business, generational conflict was constant. After Bridge Builders, we’re not just talking—we’re planning together. It’s been a game-changer.

Lena K., Tech Startup Founder

This is practical, not theory.

We didn’t need another lecture. We needed tools. Bridge Builders gave us frameworks we could use immediately, and the results showed up fast.

Daniel R., Senior Manager

BOOK A CALL BELOW TO SEE IF YOU'RE A FIT

Sample Topics We’ll Explore

  • Generational “DNA”: What shapes each generation’s mindset

  • What they meant vs. what you heard: Language decoding

  • Managing up, down, and sideways across age groups

  • Breaking stereotypes: Beyond “Boomer,” “Millennial,” and “Quiet Quitters”

  • Communication tools that build trust, not tension

  • How to hire, give feedback, and lead with generational fluency

  • Building your personal Generational Fluency Plan to use at work

How it Works

Start Date Options

Option 1 : Starts July 4, 2025 (SOLD OUT)

Option 2 : September 6, 2025 (SOLD OUT)

Option 3 : November 20, 2025

Time

Every other Thursday, 7:00 AM EST

Format

Live Zoom Sessions

Group Size

Max 6 participants

Session Length

90 minutes

Session Format

Check-in → Topic Deep Dive → Break → Hot Seat Coaching

→ Action Steps

Financial Investment

$550

Per Session

$ 3,300

Total Per Participant

Frequently Asked Questions

Here’s everything you need to know about what Charisma Lab is, how it works, and why it’s the fastest way to build unshakable presence.

Q : What if I think I already “get” other generations?

You might—but are they hearing you the way you think they are? This program isn’t about being “woke” to generational quirks—it’s about measurable leadership fluency: managing up, mentoring down, and collaborating sideways across age-based communication gaps that cost companies real money and trust.

Q : I’m not in HR. Is this still relevant to me?

Absolutely. Generational friction shows up insales conversations, client retention, team dynamics, board meetings, and everyday communication. This is about leading humans, not checking HR boxes.

Q : Will I be recorded during practice sessions?

No. Quite the opposite. We actively dismantle lazy generational clichés (“Boomers hate tech,” “Gen Z has no work ethic”) and instead teach real psychological, economic, and cultural context that shapes each group’s mindset and behavior. We’re here to challenge assumptions, not validate them.

Q : What if I’m the youngest (or oldest) in the group?

Perfect. That perspective is essential. You’ll gain new tools to communicate with influence regardless of your age, and you’ll also learn what’s often misunderstood about your generation—so you can work smarter, not harder, to be heard.

Q : Do I have to disclose personal workplace stories?

Only if you want to. Many participants choose to bring real dynamics into the “Hot Seat” sessions—but there’s no pressure. The environment is confidential, but also choice-based. You’ll learn just as much from others’ experiences as you will from sharing your own.

Q : What happens if I miss a session?

We strongly encourage full attendance, but life happens. If you miss a session, we’ll provide a short recap and action sheet. However, live interaction and real-time coaching are where the breakthroughs happen, so aim to attend all six if possible.

Q : Can my company pay for this?

Definitely. Most participants get reimbursed through leadership development or DEI training budgets. We’ll provide documentation or invoices upon request.

Q : What if generational conflict isn’t a “big” issue on our team?

It might not be visible—but that doesn’t mean it’s not there. Often, it shows up subtly: misinterpreted emails, “vibe mismatches,” missed handoffs, or quiet resentment. Fluency helps prevent small misunderstandings from becoming big culture problems.

Ready to Claim Your Seat in the

Generational Fluency Masterclass

Transform workplace tension into collaboration that drives results.

Stop struggling to “manage” generations on your own. Instead, join a small, high-trust designed to help you decode communication gaps, align diverse perspectives, and build teams that actually work together.

No conflict. No confusion. Just the clarity to lead across Boomers, Gen X, Millennials, and Gen Z—and unlock the full potential of your people.

Only 12 seats. Rolling admissions.

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