The Generationality of Work Podcast

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 intentionally transition leadership from one generation to the next. Marc shares personal reflections on growing up within a successful family business and the responsibility that comes with inheriting opportunities created by previous generations.

The conversation explores leadership, accountability, credibility and the importance of earning trust regardless of title or family connection. Marc discusses how intentionality, work ethic and leading by example have shaped his approach throughout a 30-year career, while also highlighting the challenges family businesses face in balancing legacy with adaptation.

Listeners will gain valuable insights into succession planning, multi-generational leadership, organizational culture and what it truly takes to build a business that lasts across generations.

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.

The conversation highlights the contrast between traditional, process-driven industries and newer, more creative and fast-moving sectors such as technology and AI. Younger professionals often bring innovative ideas, energy and access to capital, while more experienced professionals contribute critical judgment, industry knowledge and an understanding of long-term consequences.

This episode underscores the importance of bridging generational gaps within client service teams. When organizations successfully integrate innovation with experience, they position themselves to deliver stronger outcomes, better manage risk and create lasting client relationships. The discussion reinforces that generational diversity is not a challenge to overcome, but a strategic advantage to be harnessed.

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-thinking firms are treating compensation as a strategic tool rather than a transactional necessity. He discusses how a lack of structure, communication and leadership alignment around compensation can lead to confusion and mistrust, particularly in multi-generational work environments where expectations and perspectives vary widely.

The episode also highlights the critical role leadership plays in designing and supporting compensation strategies, rather than leaving them solely to HR to implement. Ultimately, this discussion underscores that transparency and intentionality in compensation are key drivers of trust, engagement and long-term organizational success.

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 true cultural alignment eliminates many generational conflicts, and why “A players” exist at every age. Kevin shares practical insights on building teams through rigorous hiring, clear expectations and lived accountability rather than slogans or perks.

For leaders in law firms and professional services organizations, this conversation reframes culture as a business discipline, one that directly impacts performance, trust and long-term success.

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 decision-making: how people think, act and respond when leadership isn’t in the room. As firms grow, this becomes critical because consistency, alignment and long-term success depend on it.

The conversation also dives into how leaders can intentionally shape culture across a multi-generational workforce, ensuring that expectations, communication styles and values are clearly understood and lived throughout the organization.

Whether you’re leading a firm, managing a team, or thinking about growth, this episode offers practical insight into building a culture that lasts.

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 hire can quietly erode team performance. Rob shares practical insights from matching professionals with organizations every day, explaining how leaders should rethink hiring, team composition, and what “productivity” really means in today’s workplace.

If you lead teams, hire talent, or want to build stronger, more resilient organizations across generations, this conversation offers a fresh and actionable perspective on measuring what truly matters.

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, 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. 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.