Lexlee Overton is a former trial lawyer who spent more than 30 years in the courtroom before choosing a different path. After experiencing firsthand how the legal profession can wear lawyers down, she founded Mind Over Law to help lawyers move beyond burnout and lead with greater clarity, resilience, and purpose.

Today, she works with both individual lawyers and legal teams using a science-based approach that combines mindfulness, emotional intelligence, and practical leadership tools to build healthier law firms with better performance.

WHAT'S COVERED IN THIS EPISODE ABOUT LAWYER WELL-BEING AND HIGH-PERFORMING TEAMS

The legal profession loves to reward hustle, grind it out, power through, keep your head down and just get the work done. But what if the real power comes from doing things differently?

Lexlee Overton spent decades playing by those rules until she realized something had to change. After 30 years in the courtroom, a health crisis at age 30 made her question everything about how lawyers are supposed to work. She founded Mind Over Law because she believes lawyers can be healthier, happier people and still do excellent work.

Now she works with individual lawyers and legal teams, teaching them that energy management is way more important than time management. She's discovered that when leaders work on themselves first, they naturally start building better teams.

In this episode of The Lawyer's Edge podcast, Elise speaks with Lexlee about why that "badge of honor" mentality around overwork is actually making lawyers less powerful, what happens when teams are chronically depleted, and how law firm leaders can build the kind of culture that actually attracts and keeps good people.

2:32 - Lexlee's personal breaking point and wake-up call

5:22 - The changing attitudes toward mindfulness in law

9:59 - Warning signs lawyers ignore before burnout hits

12:51 - Simple practices for skeptical, hard-driving lawyers

16:06 - The neuroscience of fight-or-flight in legal practice

18:32 - The statistics on lawyer mental health and malpractice

20:36 - Reframing the "lose your edge" mentality

23:15 - Why law firm leaders should care about well-being initiatives

26:41 - Using biofeedback to demonstrate coherency

29:12 - The one leadership habit Lexlee would change overnight

30:58 - Emotional intelligence in high-performing legal teams

37:16 - Getting started with culture change

40:04 - The curse of knowledge insight

MENTIONED IN BEYOND BURNOUT: BUILDING HIGH-PERFORMING LEGAL TEAMS THROUGH WELL-BEING

Mind Over Law | LinkedIn

American Bar Association (ABA) study on lawyer depression and substance abuse

Get connected with the coaching team: [email protected]

The Lawyer's Edge

SPONSOR FOR THIS EPISODE...

Today's episode is brought to you by the Ignite Women's Business Development Accelerator, a 9-month business development program created BY women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers AND supporting the retention and advancement of other women in the profession.

If you are interested in either participating in the program or sponsoring a woman in your firm to enroll, learn more about Ignite and sign up for our registration alerts by visiting www.thelawyersedge.com/ignite.

Ken Vrana is a Senior Director at Western Alliance’s Juris Banking Group. He specializes in crafting customized capital solutions for law firms, alternative legal service providers, and legal tech companies. With a deep expertise in complex banking relationships, he provides his clients with in-depth guidance on operating and fiduciary account setup and ongoing management, including advising on fraud mitigation tactics, advanced payables, and receivable services to streamline overall firm operations.

With over two decades of banking experience, Ken serves as a trusted advisor to stakeholders across the legal community and regularly leverages his extensive network to build meaningful connections. His unmatched dedication to navigating clients’ transactional and credit banking needs with ease underscores his long-standing commitment to legal professionals nationwide.

Prior to joining Western Alliance, he had significant tenures at Capital One and Citizens Bank, where he helped clients optimize their operations, drive growth, and enhance profitability. Ken received his Bachelor of Arts from Mount Saint Mary College.

WHAT'S COVERED IN THIS EPISODE ABOUT LAW FIRM BANKING AND FINANCIAL STRATEGY

Most lawyers master the practice of law but struggle with the business side. From managing cash flow to protecting client funds from cybercrime, the financial realities of running a law firm present challenges most lawyers were never trained to handle.

Ken Vrana works specifically with law firms to help them make smarter financial decisions and avoid common pitfalls. He sees firsthand how smaller firms are often targeted by fraudsters because they lack the robust protection systems of larger firms, and how many firms leave money on the table by not optimizing their payment processes or banking relationships.

From startup firms hanging their shingle to established practices pursuing growth through mergers, Ken shares practical insights on choosing the right banking partners, setting up proper fraud protection, and why the relationship with your banker might be more important than you think.

In this episode of The Lawyer's Edge podcast, Elise Holtzman speaks with Ken about protecting your firm's funds, streamlining cash flow, and why treating your banker as a trusted advisor could be one of the smartest business decisions you make.

1:51 - Banking challenges facing large and smaller firms

6:23 - The benefits of using specialized legal banking over a local bank branch

9:43 - Common mistakes by law firms in their banking and financial management choices

14:52 - Guidance for new law firms to start on a solid footing with legal banking

19:21 - Why legal banks like Juris see startup firms as valuable clients

21:56 - Considerations for law firms pursuing growth

23:53 - Culture mismatches as a leading cause of merger failures 

27:17 - Players who should be involved in your firm’s growth or merger

29:53 - Reasons for having multiple banking relationships

32:19 - The importance of regularly re-evaluating if a banking relationship is a good fit 

35:40 - Large firms’ lack of immunity to financial management problems, despite having more resources

37:24 - The value of banking relationships and understanding their importance

MENTIONED IN BANKING AND FINANCIAL STRATEGY FOR LAW FIRMS THAT WANT TO GROW

Connect with Ken on LinkedIn

Western Alliance Bank | LinkedIn

Get connected with the coaching team: [email protected]

The Lawyer's Edge

SPONSOR FOR THIS EPISODE…

Today’s episode is brought to you by the Ignite Women’s Business Development Accelerator, a 9-month business development program created BY women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers AND supporting the retention and advancement of other women in the profession. 

If you are interested in either participating in the program or sponsoring a woman in your firm to enroll, learn more about Ignite and sign up for our registration alerts by visiting www.thelawyersedge.com/ignite.

Kirsten Branigan was facing an existential crisis. Working at a large New Jersey law firm with young children, she felt the rubber meeting the road in a significant way. She couldn't do everything she wanted to do with her family while meeting all the firm's requirements.

Instead of just accepting the situation, Kirsten made two bold decisions. She started her own employment law firm built around flexibility and empathy. And when she heard that the New Jersey Women Lawyers Association was dying out because "women of your generation don't care about these issues," she decided to prove that wrong by leading the effort to revitalize the organization.

Twenty years later, Kirsten's firm is thriving as a refuge for women lawyers, and that "dying" organization now draws over 700 people to its annual gala. As someone currently conducting research with Rutgers University on women's advancement in the legal profession, she has insights on what's actually changing for women lawyers and what isn't.

In this episode of The Lawyer's Edge podcast, Elise Holtzman speaks with Kirsten about building a law firm culture that works for women lawyers, the challenges that persist across generations, and her advice for creating change: Build an Army.

3:24 - Why Kirsten left Big Law to start her own firm after an existential crisis 

5:51 - The values and culture Kirsten built into her firm from day one 

9:02 - How to maintain firm ideals while dealing with business pressures 

11:19 - The story of revitalizing the New Jersey Women Lawyers Association 

16:03 - Current challenges women face in the legal profession based on Rutgers research 

23:16 - Positive shifts and trends for women in law 

28:05 - The mental health crisis in the legal profession and available resources 

30:31 - Understanding generational differences and approaching them with empathy 

32:40 - What lawyers can do to make the profession better for everyone 

38:36 - Kirsten's advice for creating lasting change: Build an Army

MENTIONED IN CREATING LAW FIRM CULTURE THAT WORKS FOR WOMEN LAWYERS

KS Branigan Law PC | LinkedIn

New Jersey Women Lawyers Association | LinkedIn

NAMWOLF

New Jersey Lawyers Assistance Program

Get connected with the coaching team: [email protected]

The Lawyer's Edge

SPONSOR FOR THIS EPISODE…

Today’s episode is brought to you by the Ignite Women’s Business Development Accelerator, a 9-month business development program created BY women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers AND supporting the retention and advancement of other women in the profession.

If you are interested in either participating in the program or sponsoring a woman in your firm to enroll, learn more about Ignite and sign up for our registration alerts by visiting www.thelawyersedge.com/ignite.

Candisse Williamson is a highly accomplished General Counsel known for her creative deal-making and extensive legal expertise across the entertainment and corporate sectors. After graduating from Northwestern Law, she refined her corporate law skills, with a focus on M&A and private equity, at prestigious firms including Paul Weiss and King & Spalding. Her career then transitioned to entertainment, where she served as VP of Business and Legal Affairs at The Madison Square Garden Company, notably as lead attorney for the renowned Christmas Spectacular Starring the Radio City Rockettes.

Later, as General Counsel at Skybound Entertainment, Candisse built the company’s legal department from the ground up, overseeing all transactions in film, TV, and gaming. She is now the GC of Hartbeat, actor and comedian Kevin Hart's media company. In this role, she established the legal department and now drives strategic deal-making across film, TV, audio, live events, and branded content, all while serving as a key member of the executive team.

WHAT'S COVERED IN THIS EPISODE ABOUT BUILDING LEGAL TEAMS AND MANAGING OUTSIDE COUNSEL

Most lawyers follow predictable career paths, but some find themselves in industries where the landscape shifts constantly. Candisse Williamson made the transition from corporate M&A at top firms to building legal departments in entertainment companies, where deal structures evolve rapidly and traditional contracts often don't fit.

As General Counsel at Hartbeat, Kevin Hart's media company, Candisse has learned that success requires more than legal expertise. She's built two legal departments from the ground up, developed strategies for working effectively with outside counsel, and discovered that understanding the business is often more important than perfecting the legal details.

In this episode of The Lawyer's Edge podcast, Elise Holtzman speaks with Candisse about her journey from Big Law to entertainment, how she approaches building and managing legal teams, and practical advice for lawyers looking to work with entertainment companies.

2:34 - Why Candisse wanted a legal career and her transition into entertainment law

5:30 - The biggest challenge for Candisse as VP/General Counsel

8:06 - How Candisse built Hartbeat’s legal department from the ground up

11:09 -  Two main purposes of outside counsel and how Candisse maintains relationships 

13:56 - Candisse’s philosophy about handling difficult conversations with outside counsel

16:52 - How you can rise above the crowded field and grow a book of business as a private practice lawyer

23:18 - Why Candisse emphasizes diversity in her staffing decisions

25:43 - Challenges in the constantly evolving world of entertainment and media

30:03 - Candisse’s personality and adaptability as an attorney 

33:53 - Highly critical advice for in-house counsel

 

MENTIONED IN STRATEGY AND TALENT: HOW ONE GENERAL COUNSEL BUILDS LEGAL TEAMS AND CHOOSES OUTSIDE COUNSEL

Hartbeat | LinkedIn | Instagram

Laugh Out Loud Network: YouTube | TikTok | Instagram | Facebook | Snapchat | Twitter/X

Anthony Desimone | Making AI Work For Your Law Firm Without Compromising Security or Excellence

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE...

Today’s episode is brought to you by the Ignite Women’s Business Development Accelerator, a 9-month business development program created BY women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers AND supporting the retention and advancement of other women in the profession. 

If you are interested in either participating in the program or sponsoring a woman in your firm to enroll, learn more about Ignite and sign up for our registration alerts by visiting www.thelawyersedge.com/ignite.

Darin Klemchuk is the CEO of Klemchuk PLLC, a leading litigation, intellectual property, and business law firm based in Dallas, Texas. Klemchuk focuses his practice on IP litigation (patents, trademarks, copyrights, and trade secrets), IP enforcement and anti-counterfeiting programs, and IP strategy.  He helps clients build market share and block competitors through intellectual property law. 

Darin is also the co-founder of Engage Workspace for Lawyers, an executive suite built by and for lawyers. He writes and speaks about human performance optimization, marketing and business development, leadership, entrepreneurship, law firm culture, and intellectual property law–all designed to encourage others to rethink what it means to be a lawyer, business owner, and leader in today’s legal profession and beyond.

WHAT'S COVERED IN THIS EPISODE ABOUT LAW FIRM LEADERSHIP

Most lawyers follow the traditional path of making partner, building a book, and climbing the ladder. But what happens when you're wired differently? When the conventional approach to practicing law feels fundamentally wrong for who you are as a person and leader?

Darin Klemchuk faced exactly this crossroads. With a stable Big Law job, a second child on the way, and zero portable business, he made what most would consider a crazy decision. He walked away from partnership to build something better. Twenty years later, he's proven that leading from within can create strong results in both law and life.

In this episode of The Lawyer's Edge podcast, Elise Holtzman speaks with Darin about his journey from Big Law to entrepreneurship, his 62-minute plank hold experience, why the "platinum rule" works better than the golden rule for leaders, and how personal growth became the foundation for his firm's success.

2:06 - Darin’s “Jerry Maguire” moment of launching his firm and how he got his first clients

5:57 - How the seeds of leadership and entrepreneurism were planted in Darin’s youth

7:56 - The difference between leadership, management, and coaching 

9:38 - One critical aspect of leadership that requires self-awareness

12:49 - The plank hold method and how you can apply it in your practice

17:33 - The immense value of peer networks for business development

22:06 - Why Darin designed anti-counterfeiting software programs to protect luxury brands’ IP

23:58 - The better rule to follow for leaders with unique personality traits

28:15 - What Darin finds fascinating about the concept of happiness 

32:16 - One of the greatest tragedies you can experience when you become successful

 

MENTIONED IN LEADING FROM WITHIN: HOW PERSONAL GROWTH FUELS LAW FIRM LEADERSHIP

Klemchuk PLLC | LinkedIn | Facebook | Instagram

Engage Workspace for Lawyers | LinkedIn | Facebook | Instagram

Unbeatable Mind

Entrepreneurs’ Organization

Vistage

Think and Grow Rich by Napoleon Hill

Culture Index

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE...

Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.

To get connected with your coach, just email the team at [email protected].

Scott Love is the President of The Attorney Search Group and host of The Rainmaking Podcast, which helps attorneys, professional service firms, and B2B salespeople get more and better business from all their clients. As a prolific thought leader on the topics of rainmaking, recruiting, and leadership, he helps law firm partners mitigate risk and maximize opportunity when transitioning from one organization to another. With his nuanced understanding of high-stakes negotiations, effective partner transitions, and the delicate risks that come with complex career moves, he has placed attorneys among the Am Law 100 and 200 in corporate, finance, private equity, and investment management practices.

Scott has also written numerous articles and authored three books on his expertise, been quoted in dozens of premium publications (such as the Wall Street Journal, Bloomberg, and Business Insider), and been a popular speaker at conferences, retreats, conventions, sales meetings, and trade associations. Additionally, he served for seven years as a member of the Board of Directors of the National Association of Legal Search Consultants and is a member of the National Association for Law Placement.

WHAT'S COVERED IN THIS EPISODE ABOUT LATERAL MOVES FOR LAW FIRM PARTNERS

Law firm partners often find themselves at a crossroads, wondering if they've outgrown their current firm, or if the grass really is greener elsewhere. The thought of making a lateral move can feel risky and emotionally charged, but what if there's a more strategic way to approach these career decisions?

Scott Love, who has spent 30 years helping partners navigate these transitions, reveals that the best moves aren't driven by money or ego, but by a clear understanding of what serves your clients best. He breaks down the two main reasons partners actually leave firms, explains why some lawyers hold themselves back from reaching their potential, and shares his proven framework for evaluating whether to stay put or make a move.

In this episode of The Lawyer's Edge podcast, Elise Holtzman and Scott explore the strategic approach to lateral partner moves, the critical questions to ask before entertaining any offers, and how focusing on your clients' needs often leads to the most successful career decisions.

1:44 - How you can succeed where you are right now and fulfill your potential

4:55 - Two primary reasons why partners leave law firms

5:55 - What your main motivation for a lateral move should be

7:15 - Internal barriers that can block you from realizing your potential as a rainmaker

11:00 - Scott’s recommendations to help you navigate a lateral transition

17:20 - Two questions to consider when choosing or trying to decide between firms

20:01 - What you need to understand about compensation before you engage with new firms

23:30 - How to mitigate risk and increase the likelihood of a successful move

30:32 - Two things you can do to successfully bring your clients to a new firm

33:55 - The strategic question lawyers forget when making a major business move

MENTIONED IN STRATEGIC LATERAL MOVES FOR LAW FIRM PARTNERS

The Rainmaking Podcast 

The Attorney Search Group

“TRP 252: [Lega] Avoid Landmines in Lateral Partner Moves with Hilary Gerzhoy”

10x Is Easier Than 2x: How World Class Entrepreneurs Achieve More By Doing Less by Dan Sullivan with Dr. Benjamin Hardy

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE...

Today’s episode is brought to you by the Ignite Women’s Business Development Accelerator, a 9-month business development program created BY women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers AND supporting the retention and advancement of other women in the profession. 

If you are interested in either participating in the program or sponsoring a woman in your firm to enroll, learn more about Ignite and sign up for our registration alerts by visiting www.thelawyersedge.com/ignite.

Scott Tiedemann first joined Liebert Cassidy Whitmore as an associate in 2000 and became a partner in 2004. When his tenure as managing partner concludes on September 30th of this year, he will be focusing his energies again full-time on his practice representing public safety agencies and building the firm's private investigations practice.

Melanie Chaney is an experienced labor negotiator and litigator and served as the managing partner of the Los Angeles office before moving into her new role managing firm-wide. She is taking over as managing partner of Liebert Cassidy Whitmore, a firm of about 115 lawyers in five offices focused on representing public agencies, educational institutions, and nonprofits across California in their labor, employment, and education matters.

WHAT'S COVERED IN THIS EPISODE ABOUT SEAMLESS LEADERSHIP SUCCESSION

Most law firms struggle with leadership transitions, often waiting until the last minute to prepare a new managing partner (and creating chaos in the process). But Liebert Cassidy Whitmore has cracked the code on seamless succession planning. Since 1980, they've successfully managed four leadership transitions, each with a 15-year tenure, through a deliberate process that includes a full year of co-managing and a "long runway" for preparation.

Scott Tiedemann and Melanie Chaney reveal the secrets behind their firm's remarkable stability and growth from 40 to 115 attorneys. They share how their "firm first" philosophy, consensus-based decision making, and seven core values create a culture where everyone is "rowing in the same direction."

In this episode of The Lawyer's Edge podcast, Elise Holtzman speaks with Scott and Melanie about their proven approach to leadership succession planning and what it really takes to build a partnership that works.

2:46 - How Liebert Cassidy Whitmore approaches leadership succession planning

7:26 - The consensus-based process for selecting the next managing partner

9:52 - What qualities the firm looks for in a managing partner (hint: it's not the "hard skills")

12:19 - Melanie's journey from "this wasn't my plan" to embracing leadership

16:32 - The specific steps they took during the co-managing transition year

18:20 - What has kept the firm stable and thriving for over 40 years

20:41 - The "firm first" culture and how founding partners gave up ownership for the next generation

23:53 - How they handle culture fit issues and removing people who don't align with values

26:27 - The top challenges facing growing law firms: AI and remote work culture

29:52 - Advice for law firms seeking to strengthen their partnership

34:30 - The importance of repeatedly discussing firm values at every meeting

39:37 - What Scott and Melanie have learned from each other

42:38 - Final advice: keeping your North Star and learning to delegate effectively

MENTIONED IN PASSING THE TORCH: TIPS FOR SEAMLESS LEADERSHIP SUCCESSION

Liebert Cassidy Whitmore

Connect with Scott Tiedemann on LinkedIn

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE...

Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.

To get connected with your coach, just email the team at [email protected].

Sandra Cohen is the Co-Founder and Managing Partner of Cohen & Buckmann, which specializes in executive compensation, employee benefits and pensions. Her firm is nearly ten years old and is highly ranked in Chambers USA Guide and The Legal 500, no small achievement for a young, small boutique firm. She is a frequent author and speaker and is a former adjunct professor at NYU Law School, where she taught pension law to the next generation of employee benefits lawyers. She's a big believer that although her business has a bench of deep expertise and scholarship, it's really relationships and referrals that built her firm.

WHAT'S COVERED IN THIS EPISODE ABOUT BUSINESS DEVELOPMENT THAT ACTUALLY WORKS

Starting your own law firm takes much more than being a good lawyer, including the willingness and ability to master business development skills that many lawyers find intimidating or distasteful. But what if effective business development isn't about sales pitches or aggressive marketing? What if it's really about making friends and building genuine relationships over time?

In this episode of The Lawyer's Edge podcast, Elise Holtzman sits down with Sandra Cohen, Co-Founder and Managing Partner of Cohen & Buckmann. Sandra shares how she built her practice through relationships rather than traditional sales tactics, the power of content marketing for credibility-building, and why business development is like "watering a tree," slow, steady, and requiring patience for long-term growth.

Sandra also discusses practical strategies for thought leadership (even for younger lawyers who think they don't have anything original to say), the importance of peer networking groups, and how giving away business can actually strengthen your referral network.

2:23 - Sandra's transition from large law firms to starting her own boutique practice 5:21 - How to track referrals and understand where your clients really come from 6:19 - The role of content marketing and thought leadership in building credibility 8:39 - Why lawyers need to show what they know, not just know it 11:41 - Advice for younger lawyers intimidated by "thought leadership" 15:04 - Getting started with writing: "Two big mistakes" instead of treatises 16:16 - How Sandra got involved in speaking opportunities through bar associations 18:01 - The power of repurposing content and LinkedIn for visibility 19:17 - Sandra's advice for senior lawyers: "Don't stumble over something that's behind you" 23:19 - The "know, like, trust, and remember" framework for relationship building 25:47 - Building peer groups that turn into 22-year referral relationships 27:21 - The power of giving away business to build your network 29:16 - How social media creates "top-of-mind awareness" for referrals 32:26 - Why business development for sophisticated practices is a long game 34:34 - Finding your audience: being in rooms full of people with problems you can solve

MENTIONED IN THE LONG GAME OF BUSINESS DEVELOPMENT THAT ACTUALLY WORKS

Cohen & Buckmann | LinkedIn

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE...

Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.

To get connected with your coach, just email the team at [email protected].

Anthony M. DeSimone is a leading advocate for integrating generative AI into the legal profession, specializing in helping law firms harness AI to enhance efficiency, profitability, and client service. With more than 25 years of experience as a CPA and CMA, Anthony began his career at Deloitte before transitioning to focus on business optimization. Today, he operates "You're the Expert Now, LLC" and serves as a faculty member at the University at Buffalo Center for Entrepreneurial Leadership.

In addition to delivering keynote presentations at national conferences, Tony leads AI accelerator courses and shares insights through his YouTube channel and podcast, "AI Mastermind." His groundbreaking work, including publishing a book in under 24 hours and producing AI-generated illustrations, underscores his expertise at the intersection of AI, data, and legal practice.

WHAT’S COVERED IN THIS EPISODE ON AI STRATEGY FOR LAW FIRMS

Many law firms are intrigued by AI, but unsure how to move forward. Questions about confidentiality, security risks, and the reliability of AI tools leave many lawyers hesitant, and expose firms to risks they don’t fully understand.

But AI isn’t about replacing lawyers. It’s about amplifying their capabilities while safeguarding client trust. Firms that learn how to integrate AI strategically will not only protect sensitive data but also position themselves for greater efficiency, profitability, and resilience in a changing legal landscape.

In this episode of The Lawyer’s Edge Podcast, Elise Holtzman talks with Anthony DeSimone, a CPA, CMA, and AI strategist who advises law firms on safe and effective AI adoption. Tony shares practical insights on the risks lawyers can’t afford to ignore, how to train teams to use AI responsibly, and how the right AI strategy can streamline firm operations without sacrificing security or professionalism.

2:10 – How law firms are approaching AI today — early adopters versus laggards

4:20 – The hidden risks when lawyers use AI tools without firm oversight

6:00 – What AI hallucinations are and why they matter for law firms

8:42 – Practical ways lawyers are using AI now — drafting, research, and more

13:14 – How to safeguard client confidentiality when using AI

17:23 – The leadership role in encouraging smart AI experimentation

21:35 – Why large language models struggle with numbers and how that impacts legal work

24:50 – What’s next — how AI will reshape law firm operations in the next five years

MENTIONED IN ANTHONY DESIMONE | MAKING AI WORK FOR YOUR LAW FIRM WITHOUT COMPROMISING SECURITY OR EXCELLENCE

You're the Expert Now, LLC | LinkedIn

AI Usage Policy Maker

Managing Partner Forum

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE…

Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.

To get connected with your coach, just email the team at [email protected].

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.

MENTIONED IN WHY I FIND YOU IRRITATING: NAVIGATING GENERATIONAL FRICTION AT WORK

Chris DeSantis | Chris DeSantis on LinkedIn

Cubicle Confidential Podcast

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

Different: Escaping the Competitive Herd by Youngme Moon

Social: Why Our Brains Are Wired to Connect by Matthew D. Lieberman

Mary Abbajay on The Lawyer’s Edge Podcast

Get connected with the coaching team: [email protected]

The Lawyer’s Edge

SPONSOR FOR THIS EPISODE…

Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.

Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.

To get connected with your coach, just email the team at [email protected].