Chris DeSantis | Why I Find You Irritating: Navigating Generational Friction at Work

Talk to any senior partner in a law firm, and you’re likely to get a complaint or snide comment about the younger generation of lawyers being lazier, more entitled, and less interested in making partner or assuming leadership roles than their predecessors. On the flip side, some younger lawyers will be all too happy to tell you that senior lawyers are overly demanding, can’t respect boundaries, won’t share origination credit, and refuse to cede any responsibility or authority to those coming up behind them.

Generational differences are real. They are significant. And they are impacting both how law firms operate today and how they will be governed in the future. 

Chris DeSantis is a speaker, author, and consultant specializing in workplace interventions. With nearly 30 years of experience as an independent organizational behavior consultant, Chris is a trusted partner to some of the world’s largest companies in the professional services, tech, and pharmaceutical industries. When working with clients, his goals are to dig deeper, treat the root causes, and offer user-friendly solutions aligned with company initiatives.

Before becoming an independent consultant, Chris was the Director of Management Development and Training for the American Medical Association and a Human Resources Development Manager at Brunswick Corporation. Chris has a BBA from the University of Notre Dame, an MA in organizational behavior from Loyola University in Chicago, and an MBA from the University of Denver.

Chris is the Author of Why I Find You Irritating: Navigating Generational Friction at Work. He’s also the Host of the Cubicle Confidential podcast, where he and Co-host Mary Abbajay share advice on outrageous workplace questions, comments, and concerns.

WHAT’S COVERED IN THIS EPISODE ON NAVIGATING GENERATIONAL FRICTION AT WORK

Many law firm leaders are grappling with generational tensions that quietly undermine collaboration, leadership development, and retention. But these conflicts aren’t simply about age, they’re rooted in deeper divides over authority, feedback, and what lawyers expect from the workplace.

Chris DeSantis, speaker, consultant, and author of Why I Find You Irritating: Navigating Generational Friction at Work, has spent his career helping organizations navigate workplace dynamics, and now helps law firm leaders understand how generational habits and mindsets can create hidden friction.

In this episode of The Lawyer’s Edge, Chris joins Elise Holtzman to unpack how law firm hierarchies clash with younger lawyers’ expectations of dialogue and inclusion. He shares why traditional “figure it out” leadership no longer works, and how shifting to a culture of open conversation can reduce friction, boost engagement, and strengthen leadership pipelines.

2:43 – Why law firm leaders can’t ignore generational friction. Chris shares the challenges that inspired him to write his book.

4:55 – How generalizations shape perceptions and create blind spots in the workplace.

7:43 – The four generations in today’s workforce and how their life experiences influence expectations at work.

11:02 – How different parenting models have shaped generational behaviors and workplace dynamics.

14:06 – Why younger attorneys struggle in tell-do workplaces, and how leaders can shift to an engage-discuss model.

19:02 – The hidden reasons adjacent generations experience the most friction, and how leaders can help defuse the tension.

26:01 – How gender, hierarchy, and generational differences collide in law firm environments.

33:10 – What leaders can do to foster dialogue over directives. Chris explains why this approach drives better performance and retention.

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