The Generationality of Work Podcast

In this episode of The Generationality of Work, Jon Sheppard sits down with Matthew Uretsky, Partner at Brown Rudnick LLP and a member of the firm’s Corporate Practice Group and Emerging Growth Companies & Venture Capital Group, for a conversation about how the role of the trusted advisor is evolving.

Matthew discusses why technical expertise alone is no longer enough to differentiate a lawyer. Trust often begins before a formal engagement, through the way attorneys listen, communicate, give candid advice, follow through and demonstrate that they are genuinely thinking about the client’s long-term interests.

The conversation also explores what younger lawyers can begin developing from the earliest stages of their careers. While technical knowledge takes time to build, emotional intelligence, curiosity, reliability and the ability to make clients feel understood can start on day one. Matthew explains why those relationship skills can be just as important in determining who ultimately becomes a trusted advisor.

Jon and Matthew also discuss networking with greater purpose. Building relationships not simply to expand a contact list, but to create a network of people and expertise that can help solve clients’ broader business needs. At the center of the conversation is a simple idea: the next generation of clients will continue to value expertise, but the lawyers who stand out will be those who combine that expertise with trust, judgment, relationships and a genuine commitment to being useful.

In this episode of The Generationality of Work, Jon Sheppard sits down with Jamaal Jones, Founder & Health Law Attorney at Jones Health Law, for a conversation about entrepreneurship, mentorship, professional development and what it means to build the kind of firm you could not find for yourself.

Jamaal shares how he approaches developing young attorneys and interns by giving them meaningful exposure to the actual practice of law. Rather than limiting early-career professionals to administrative work or isolated assignments, he brings them into meetings, networking events, writing opportunities and other real-world experiences that help them understand how attorneys build relationships, communicate and grow professionally.

The conversation also explores Jamaal’s belief that mentorship and learning should move in every direction. He discusses the value of bringing people together in person, creating space for open dialogue and using practices like monthly roundtables to encourage ideas, feedback and collaboration across generations.

Jon and Jamaal also discuss the role teaching plays in Jamaal’s own development. As healthcare law continues to evolve, including the growing influence of artificial intelligence.

At the center of the conversation is a broader idea about leadership: creating environments where people can gain confidence, contribute meaningfully, learn from one another and ultimately pay that investment forward.

In this episode of The Generationality of Work, Jon Sheppard explores what he calls the “relationship succession horizon." The growing challenge organizations face as long-standing client relationships, leadership roles and institutional knowledge begin transferring from one generation to the next.

Over the next decade, many businesses and professional-services organizations will confront a significant shift as experienced leaders retire, younger professionals take on greater responsibility, and client relationships that may have been built over decades need to be successfully transitioned. Jon discusses why those relationships cannot simply be handed from one person to another and why trust, communication, mentorship and intentional relationship-building will play an increasingly important role in succession.

The episode also looks at the responsibility organizations have to prepare the next generation before a transition becomes urgent. Developing future relationship leaders means giving younger professionals meaningful exposure to clients, helping them build credibility and creating opportunities for relationships to deepen over time rather than waiting until a senior leader is preparing to leave.

As generational change reshapes both the workforce and the client base, organizations that plan for relationship succession early will be better positioned to preserve trust, retain clients, develop future leaders and create continuity for the years ahead.

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.

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.

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.

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.

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.

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.

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.