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.