Podcast
The Generationality of Work
Conversations about leadership, workplace culture, mentorship, technology and what it takes to lead across generations.

Hosted by Jon Sheppard, The Generationality of Work explores how people from different generations communicate, lead, collaborate, build relationships and navigate the changing workplace.
Through conversations with leaders across law, business, professional services, technology and other industries, the podcast looks beyond generational stereotypes to examine the real challenges and opportunities shaping today’s workforce.
Conversations About the Changing Workplace
Today’s workplace brings together multiple generations with different experiences, expectations, communication styles and perspectives.
The Generationality of Work explores what those differences mean for leadership, mentorship, client relationships, organizational culture, technology, career development and the future of work.
Some episodes feature conversations with business and industry leaders. Others give Jon an opportunity to explore a specific workplace issue directly. The goal is the same: practical conversations that help people better understand one another and build stronger organizations.
About the Host
Jon Sheppard is a legal recruiter, multigenerational workforce advisor, speaker and host of The Generationality of Work.
Drawing on more than 40 years of conversations with attorneys, business leaders, executives and professionals, Jon brings a practical perspective to the challenges of leadership, communication, workplace culture, career development and generational change.
Latest Episode
New episodes are posted regularly. Press play below, or listen on Apple Podcasts.
Interested in Joining the Conversation?
The Generationality of Work features leaders and professionals with meaningful perspectives on leadership, workplace culture, business, mentorship, technology and the changing world of work.
If you or someone you know would be a strong fit for the podcast, we’d love to hear from you.
From Conversation to Practice
The themes explored on The Generationality of Work directly relate to J. Sheppard Associates’ work with organizations navigating the challenges of a multigenerational workforce and their recruiting needs.
Through speaking, facilitated conversations, workshops and advisory services, JSA helps organizations improve communication, collaboration, leadership, accountability and performance across generations while finding talented individuals that fit with a firm or company’s culture, vision and long term success.
