The Generationality of Work Podcast

In this episode, Jon Sheppard sits down with Peter Cifichiello, Partner at Casner & Edwards, LLP, to explore how different generations build, grow and ultimately exit businesses. Together, they examine why succession planning is about far more than legal documents or financial transactions. It's about understanding the people behind the decisions. Drawing from his extensive experience advising...

In this episode of The Generationality of Work , Jon Sheppard welcomes Nicole Suriano (Leydon), Paralegal at Brandon J. Broderick, Attorney at Law, for a thoughtful conversation about parenthood, professional identity, workplace culture and personal growth in today's legal profession. Nicole shares her perspective on balancing career development with family life while navigating the evolving expec...

In this episode of The Generationality of Work , Jon Sheppard sits down with Marc Landow, Partner at Landow and Landow Architects, to explore the realities of succession planning inside a family business that has successfully operated for more than a century and is now in its third generation. Together, they examine why succession is often misunderstood and why many family firms drift rather than...

In this episode of The Generationality of Work , Jon Sheppard sits down with Mike Kaufman, Partner at Kaufman Organization, to explore how multi-generational client service teams can either strengthen or challenge business outcomes. Drawing on decades of experience in New York real estate, Mike shares his perspective on how different generations approach decision-making, risk and client service. T...

In this episode of The Generationality of Work , Jon Sheppard is joined by Mark Shore, President of Atlas Consulting Services, to explore the evolving role of compensation in today’s workplace. The conversation goes beyond salary to examine how compensation, including benefits, serves as a reflection of an organization’s values, priorities and overall culture. Mark shares insights on why forward-t...

In this episode of The Generationality of Work , Jon sits down with Kevin Daisey, Founder and Director of Business Development at Array Digital and host of the Managing Partners Podcast, to unpack a hard truth about organizational culture: culture isn’t what you say, it’s what you do. We explore why stated values and branding mean little if everyday behaviors don’t reinforce them, how hiring for t...

What does culture really mean inside a law firm and how do you scale it across generations? In this episode of The Generationality of Work , Jon Sheppard is joined by Damien Weinstein and Brian Klein, Co-Founders of Weinstein & Klein, to unpack “the culture equation” and why culture is far more than a mission statement or set of values. Together, they explore how culture is actually defined by...

What if productivity isn’t about hours at all? In this episode of The Generationality of Work , Jon sits down with Rob Levin , Cofounder and Chairman of WorkBetterNow , to challenge one of the most entrenched ideas in professional services: that time equals value. Together, they explore why time-based metrics persist, how cultural fit often matters more than technical skill, and why one misaligned...

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 Adv...

In this episode of The Generationality of Work , Jon 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. Andr...

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 credibil...

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,...

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 , joi...

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, an...

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 — a...

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 explo...

 What does the generationality of work really mean? To some, it’s about flexibility. To others, purpose, stability, or opportunity. In today’s workforce, Boomers, Gen Xers, Millennials, and Gen Z aren’t just different — they’re often judging each other through generational lenses . With over 40 years of recruiting experience, host Jon Sheppard has heard it all. In The Generationality of Work Podc...