The Generationality of Work Podcast

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.

The Generationality of Work Podcast is a business podcast hosted by Unknown Host, with 20 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts The Generationality of Work Podcast, a business show with 20 episodes published.

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  Episode #19

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

  Aug 10, 202643 min

  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.

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  Episode #18

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

  Jul 27, 202639 min

  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.

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  Episode #17

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

  Jul 13, 202626 min

  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.

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  Episode #16

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

  Jun 29, 202632 min

  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.

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  Episode #14

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

  Jun 1, 202634 minS0

  <p>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.</p><p>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.<...

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