In this episode of The Generationality of Work, we explore the theme of work as dignity through a unique conversation with students and faculty from Cristo Rey New York High School, a school known for its innovative Corporate Work Study Program.

The episode features three seniors, Aiden, Laura & Valeria, currently participating in the program, along with Alexandra Castellano, Director of Advancement, and Angela Acevedo, Vice President - Corporate Work Study. Together, they share what it means for young people to enter the professional world while still in high school, balancing academic responsibilities with real workplace expectations.

Through their stories, the students describe how mentorship, recognition, and meaningful responsibility help shape their confidence and professional identity. Their perspectives challenge common assumptions about younger generations and highlight how thoughtful leadership and supportive workplace environments can empower emerging talent.

The conversation also explores what organizations can learn from programs like Cristo Rey’s; particularly the importance of treating young professionals as contributors, recognizing growth and creating environments where learning and dignity in work go hand in hand.

Cristo Rey New York High School’s mission will also be celebrated at its upcoming “Magic of Cristo Rey” annual event this May, which supports the continued growth of the school and its Corporate Work Study Program.

This episode offers a powerful reminder that mentorship, opportunity and dignity in work can shape not only careers, but lives.

In this episode of The Generationality of Work, John speaks with Andrew Singer, Managing Partner of Tannenbaum Helpern, about the growing importance of succession planning as the legal industry faces the coming “Silver Tsunami.”

Together, they explore how law firm leaders can prepare for generational transitions while protecting long-term client relationships and maintaining firm stability. Andrew shares practical insights on why communication among partners and leadership is often underestimated in succession planning, how firms can minimize the risk of client attrition when senior partners transition or retire, and why building institutional client relationships, rather than relationships tied to a single lawyer, is critical for long-term success.

The conversation also highlights strategies for developing younger lawyers, giving them meaningful opportunities to build client relationships and take on leadership roles, while encouraging collaboration across practice groups to strengthen the depth and breadth of the firm’s client service.

For managing partners, firm leaders, and lawyers thinking about the future of their organizations, this episode offers valuable perspective on how thoughtful succession planning, strong communication, and team-based client relationships can help firms navigate generational change while continuing to grow.

In this episode of The Generationality of Work, we’re joined by Ron Geffner, former SEC Enforcement Attorney and founding partner of Sadis & Goldberg LLP, for a candid conversation about what leadership really looks like inside a modern law firm.

Ron shares hard-earned lessons from building and managing teams over decades in private practice, reflecting on how trust, communication and credibility shape everything from associate development to firm growth. He explains why vulnerability can be a strength, how attorneys’ natural risk-aversion can lead to negative assumptions and why consistent transparency from leadership prevents fear and disengagement across generations.

The discussion also explores the realities of running a firm, learning from mistakes without dwelling on them and why leadership is judged not in single moments, but in patterns over time.

At its core, this episode is about one simple truth: people don’t follow titles. They follow leaders they trust. For founders, executive committee members and rising professionals alike, this conversation offers practical perspective on building cultures where credibility, resilience and generational fluency drive long-term success.

Generational fluency isn’t about age, stereotypes or personality types. It’s about understanding how different generations define trust, credibility, risk and value.

Today's guest is Chase Steinberg, First Vice President & Senior Commercial Relationship Manager at Valley Bank.

In this conversation, Chase shares how navigating founders, successors and emerging leaders requires reading the room, honoring legacy and building parallel relationships up, down and across generations. From asking the right opening question to adapting tone, pacing, and communication style, Chase breaks down how real influence is built—not through authority alone, but through authenticity, alignment, and trust.

Together, we explore how generational fluency becomes a strategic advantage in banking, leadership, succession planning and long-term client relationships; and why those who master it don’t just preserve legacy, they extend it.

For decades, professional careers—especially in law firms—have been built around a ladder: predictable steps, fixed timelines, and a narrow definition of success. But as clients, teams, and workplaces have changed, that model no longer reflects how great professionals actually grow.

In this episode, Edward Weisz, Partner and Co-Chair of Patent Prosecution & Counseling at Cozen O'Connor, joins Jon Sheppard to explore the difference between career ladders and career lattices—and why readiness, judgment, and trust matter more than titles or tenure.

Drawing from Ed’s own path from an IP boutique to firm leadership, the conversation looks at how early-career lawyers build real capability by wearing multiple hats, being mentored, and learning to manage client expectations. Ed and Jon dig into how responsiveness, communication, and service are what truly make lawyers indispensable—both to clients and to the partners who decide who gets promoted.

They also explore how generational change, remote work, and shifting client relationships are forcing firms to rethink how they evaluate people. Advancement today isn’t just about climbing upward—it’s about building visibility, trust, and credibility across a network of people inside and outside the firm.

As Ed puts it, growth no longer happens in a straight line—it happens across a lattice, where learning sideways, mentoring, collaboration, and accountability determine who is ready for the next level.

As firms face the coming “silver tsunami” of senior leaders stepping back, the real question isn’t who has the longest tenure — it’s who still has credibility.

In this episode, Craig Gambardella, Partner and Executive Committee member at Kucker Marino Winiarsky & Bittens, LLP (and a mid-career leader inside a major law firm), joins Jon Sheppard to unpack why credibility is no longer static — and why that shift is reshaping succession planning across every professional services firm.

Craig explains why many firms fail at succession because they treat it as a future event instead of a daily discipline, and why intentional, fair, and transparent leadership is the true prerequisite for successful transitions. When credibility is strong, succession becomes natural. When it’s weak, infighting, hoarding of power, and legacy anxiety take over.

They also dive into how generational alignment now drives client retention. As younger general counsels and business leaders rise, firms that rely on aging rainmakers without building next-generation relationships risk losing accounts entirely. Craig shares how clients are increasingly choosing leaders who can speak their language — not just inherit their files.

Together, Jon and Craig explore how firms can reframe letting go as legacy building, why putting younger leaders in real decision-making seats creates trust across generations, and how credibility is built the same way fitness is: by showing up, being visible, staying transparent, and putting in the reps every day.

If your firm is staring down leadership transition, client turnover, or the pressure of generational change, this conversation shows how credibility — not title — is what carries a business into the future.

Joe Colarusso never set out with a 40-year career map. From Teach for America classrooms in Brownsville, Brooklyn to public defense law, charter schools, nonprofits, and advisory work, his journey has been shaped by pauses, pivots, and a steady pull toward impact over comfort.

In this conversation, Joe shares how witnessing systemic inequity, inheriting his grandfather’s commitment to service, and learning through both success and failure pushed him toward a non-linear career built on purpose rather than titles. What may look like a winding résumé is actually anchored by one constant: a deep desire to help people and create meaningful change.

Joe also explores the difference between endurance and resilience — surviving hard seasons versus using them to discover what you’re capable of. Whether it was going to law school, changing industries, or taking a leap with the support of his husband, Joe reveals how betting on yourself becomes the foundation for long-term growth.

Together, Joe and Jon dive into imposter syndrome, identity beyond job titles, and how self-knowledge helps you navigate generational shifts, career misreads, and uncertainty in today’s workplace.

If you’ve ever worried that your career is too messy, too slow, or too unconventional, this episode is a reminder:

your path doesn’t have to be linear to be meaningful.

Work means different things to different generations—and that difference is at the center of today’s workplace challenges.

In the pilot episode of The Generationality of Work Podcast, Jon Sheppard draws on 40 years of recruiting experience to explain how each generation brings its own values, expectations, and needs into the workplace. From boomers and Gen Xers to millennials and Gen Z, Jon explores how personal life and work life intersect, how “need sets” shape behavior, and why feeling seen and heard matters at every stage of a career.

With four generations working together for the first time, what feels reasonable to one group can feel unfamiliar to another. This episode introduces the core themes of the podcast: communication, accountability, work-life rhythm, and understanding what drives people individually—not generational stereotypes.

This podcast is about helping people find a way forward together, improving outcomes for clients, retaining great talent, and creating workplaces where people can thrive by understanding that work doesn’t mean the same thing to everyone.