Foundational Fridays: Embracing Generational Diversity: A Conversation with Jonathan Sheppard on Navigating the Multigenerational Workplace

Breakfast Leadership Show

Jonathan Sheppard is President and CEO of J. Sheppard Associates, a full-service Attorney Search and executive Placement firm servicing top-tier mid-to-large-size law firms, corporations, and nonprofits. Having spent his entire career in the recruiting industry, starting at 19 years old, Jon founded J. Sheppard Associates in January 2000 to place lateral partners, associates, and executives across the legal landscape.

Operating from the prism of generational inclusiveness, “The Generationality of Work Today,” Jon advocates for all four generations. “ As Jon says, “We have four generations working together trying to figure each other out. This “generationality” and its issues have brought Jon to The Breakfast Leadership podcast today.

Beyond his search business and being a “generational advocate,” Jon also enjoys working on behalf of various charities on issues he is passionate about—currently a board member for Goodwill NYNJ. Jon is also the former NYC board chair for Easter Seals, and his charitable work extends to New York Cares, the 911 Memorial and Museum, The Cristo Rey NY High School, and other notable charities. An avid runner, Jon has completed seven NYC Marathons. He generally enjoys an active lifestyle of golf, paddleboarding, gardening, and outdoor activities with his wife, Susan, and stepchildren in Huntington, New York.

To view the videos on “The Generational of Work Today” on Linked In, follow this page :

https://www.linkedin.com/company/j.sheppard-associates/

And on Instagram here:

https://www.instagram.com/jsheppardassociates/

Show notes:

Summary Introductions and background @ 0:00

Jonathan shares his background in recruiting and noticing generational differences in the workplace. He discusses how embracing different perspectives across generations can strengthen organizations.

Generational differences in the workplace @ 3:32

Jonathan discusses the four generations now coexisting in workplaces for the first time. Each generation has different needs that must be understood to maximize performance and engagement. Partners must make an effort to communicate effectively with younger associates.

Creating an environment for growth @ 25:15

Jonathan emphasizes creating a culture of courtesy, respect, and accountability where different opinions are encouraged. Michael shares how hiring based on coachability and interpersonal skills allowed an employee to thrive far beyond expectations.

The importance of communication and accountability @ 28:36

Regular communication and accountability are vital, including self-accountability. Younger workers want mentors present, while partners must be engaged to effectively lead. Progressive firms listening to all generations will be positioned for success.

Navigating future changes and opportunities @ 30:25

While changes continue, focusing on including diverse views and giving people stake in decisions prepares organizations to withstand challenges. The conversation emphasizes extending beyond comfort zones and bridging generations through open communication.