The Generationality of Work Podcast

Jon Sheppard
  • 5.0 (2)
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The Generationality of Work explores one of the most important leadership challenges facing organizations today: how to build stronger, more effective teams across generations and turn generational friction into organizational strength. Hosted by Jon Sheppard, a legal recruiter and advisor who works closely with law firms and professional organizations, the podcast features conversations with managing partners, founders, executives, and industry leaders who share practical insights on leadership, culture, talent strategy, and the evolving workplace through the generational lens. Each episode examines how generational perspectives shape communication, collaboration, and decision-making inside organizations and how leaders can turn generational differences into a strategic advantage rather than a source of friction. Through thoughtful discussions and real-world experiences, The Generationality of Work provides leaders with actionable ideas for strengthening organizational culture, developing talent, improving collaboration and preparing their firms and companies for the future of work.

  1. 2d ago

    Reinventing a Legacy Business: How EOS, Leadership, Technology and Letting Go Can Transform a Business and Your Life with Gordon Coyle

    In this episode of The Generationality of Work, Jon Sheppard sits down with Gordon Coyle, Principal & Chief Risk Architect at The Coyle Group, for a conversation about what it takes to reinvent a legacy business and transform the way you lead it. Gordon shares lessons from evolving a nearly century-old family business, including the role of EOS, technology, leadership, delegation and ambitious goal-setting. He discusses why meaningful growth often requires entrepreneurs to confront the fears that keep them from making major changes. Whether that means giving up control, investing more aggressively, building a larger team or rethinking the systems that have guided the business for years. The conversation also explores the idea of “unique ability." Identifying the work that gives a leader energy, creates the greatest value and is difficult for others to replicate. Gordon explains why entrepreneurs can become bottlenecks when they stay too involved in work that someone else could handle just as well and why letting go can create more opportunity for both the organization and the people within it. Jon and Gordon also discuss setting goals that may seem almost unreachable today and then working backwards to determine what needs to change to make them possible. From systems and structure to mindset and leadership, the episode offers a practical look at how business transformation can ultimately change not only the company you build, but the life you are able to create around it.

  2. Aug 24

    The Relationship Economy: Why Real Estate Law is Still Built on Human Trust with Aaron Strauss

    In this episode of The Generationality of Work, Jon Sheppard sits down with Aaron Strauss, Managing Partner at A.Y. Strauss LLC, for a conversation about why the legal profession, and real estate law in particular, is still built on trust, relationships and human judgment. Aaron discusses the importance of integrity and how doing the right thing, even when no one is watching, helps build the kind of trust that strengthens client relationships, teams and firm culture. He also explains why firms should look for people who can become trusted cultural ambassadors and contribute to an environment where others feel supported and connected. The conversation also explores how the next generation of lawyers develops. Aaron shares why talented junior attorneys need meaningful responsibility, but also the right guidance and mentorship around them. He reflects on the value of learning through observation. Watching experienced professionals communicate with clients, work with colleagues and navigate difficult situations. And why many of the most important lessons in a legal career can’t be taught through a formal playbook. Jon and Aaron also discuss law firm culture, professional development, leadership and the long-term value of investing in people. At the center of the conversation is a simple idea: technical skills matter, but trust, judgment, mentorship and strong relationships are what ultimately sustain successful careers, teams and organizations.

  3. Aug 10

    Mentoring and Training Young Attorneys - A Conversation About Mentoring Across the Generations with Michael Jaffe

    In this episode of The Generationality of Work, Jon Sheppard sits down with Michael Jaffe, Partner at Pazer Epstein Jaffe Fein & Gozenput, P.C., for a candid conversation about mentoring and training the next generation of attorneys. Together, they discuss why professional development must go beyond completing assigned work and how young lawyers can build stronger judgment, take greater ownership of their careers and better understand the business of law. Michael also shares his perspective on the commitment required to grow from associate to partner, including the importance of client service, business development and contributing to the long-term success of a firm. The conversation also explores the role of AI in legal practice and why attorneys should learn to use it thoughtfully to become more productive, strategic and effective, without losing the critical thinking, judgment and relationship-building skills that remain essential. A practical discussion about mentorship, ambition, technology and what it takes to build a successful legal career across generations.

  4. Jul 27

    Trauma, Burnout and Performance: Understanding How Life Experiences Impact Productivity, Communication and Trust with LeiLani Quiray

    How do trauma, burnout, and life experiences influence the way people show up at work? In this episode of The Generationality of Work, Jon Sheppard welcomes LeiLani Quiray, Founder & CEO of be the change HR, for an engaging conversation about creating healthier workplace cultures through empathy, communication, and intentional leadership. Together, they explore why stress and burnout are no longer topics organizations can afford to ignore. Rather than expecting employees to simply push through challenges, Jon and LeiLani discuss the importance of equipping teams with the resources, education, and support they need to manage stress, build resilience, and perform at their best. Whether you're a leader, HR professional, manager, or individual contributor, this episode offers practical insights into fostering a workplace where people feel supported, valued and empowered to succeed.

  5. Jul 13

    Why Multigenerational Leadership is Transforming Team Culture, Retention, and Long-term Business Success with Kristen Fortino

    In this episode of The Generationality of Work, Jon Sheppard sits down with Kristen Fortino, VP of Business & Investment Strategy at Metropolis Group and Founder & Head of Sales & Partnerships at Relm, for a conversation about leadership, innovation, AI and the future of commercial real estate. Together, they explore how multigenerational leadership is shaping workplace culture, driving stronger collaboration and helping organizations adapt to rapidly evolving technology. Kristen shares how Metropolis Group and Relm work together to combine artificial intelligence with human expertise, demonstrating that the greatest value comes not from replacing people, but from empowering them with better tools. The discussion examines how AI is transforming due diligence, property research, compliance and decision-making while emphasizing the continued importance of experience, judgment, communication and trust. Jon and Kristen also discuss leadership, employee development, organizational culture and why successful companies view technology as an extension of their team rather than a substitute for it.

  6. Jun 29

    From Founder to Exit: How Each Generation Builds and Sells a Business Differently with Peter Cifichiello

    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 founders, family businesses and closely held companies, Peter shares how each generation approaches entrepreneurship, leadership, risk and long-term planning through a different lens. The conversation explores how life stage influences decision-making, why founders often struggle to transition leadership and how generational perspectives can either create friction or become a strategic advantage. Jon and Peter also discuss business succession, founder identity, organizational evolution, communication and the importance of aligning family, leadership, and ownership goals. Whether you're building a company, preparing for an exit, or helping guide the next generation of leaders, this episode offers practical insights into navigating change with intention.

  7. Jun 15

    The Human Side of Legal Work: Parenthood, Identity and Professional Growth with Nicole Suriano

    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 expectations of a multigenerational workforce. Together, she and Jon explore how leadership, emotional intelligence, flexibility, accountability and authenticity influence employee engagement and organizational success. Listeners will gain practical insights into leadership, workplace culture, employee engagement, burnout prevention, generational expectations and the human side of professional growth in modern organizations.

  8. Jun 1

    The Myth of Succession: Why Most Family Firms Drift and Don’t Actually Transition with Marc Landow

    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.

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About

The Generationality of Work explores one of the most important leadership challenges facing organizations today: how to build stronger, more effective teams across generations and turn generational friction into organizational strength. Hosted by Jon Sheppard, a legal recruiter and advisor who works closely with law firms and professional organizations, the podcast features conversations with managing partners, founders, executives, and industry leaders who share practical insights on leadership, culture, talent strategy, and the evolving workplace through the generational lens. Each episode examines how generational perspectives shape communication, collaboration, and decision-making inside organizations and how leaders can turn generational differences into a strategic advantage rather than a source of friction. Through thoughtful discussions and real-world experiences, The Generationality of Work provides leaders with actionable ideas for strengthening organizational culture, developing talent, improving collaboration and preparing their firms and companies for the future of work.

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