Lawyerist Podcast

Lawyers may soon spend less time opening applications, and more time simply telling AI what needs to happen next. In episode 630 of the Lawyerist Podcast, Zack Glaser talks with innovation strategist Sam Harden about the rise of agentic AI and how tools like ChatGPT Work and Claude Cowork could reshape the way legal professionals work. 

Unlike a traditional chatbot, an agentic system can operate within a workspace, analyze groups of files, create and update documents, develop plans, and connect information from different sources. That could allow lawyers to access emails, calendars, case materials, research, and practice management information through a single working interface. 

Zack and Sam discuss what this means for law firms filled with open Word documents, browser tabs, PDFs, research databases, and disconnected software. They also challenge the idea that AI should perform the most sophisticated legal reasoning while lawyers clean up the formatting. Instead, AI should take on the repetitive administrative work so lawyers can operate at the top of their licenses. 

If you want to understand where legal AI is heading beyond prompting and summarization, this episode offers a grounded look at the tools, opportunities, risks, and experiments shaping the next phase of legal work. 

Listen to our previous episodes on Agentic AI, Law Firm Workflows & the Future of Legal Work. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction 

00:18 – What the World Cup Teaches About Professionalism 

05:19 – Meet Sam Harden 

06:25 – The “Claudification” of ChatGPT 

08:15 – From Chatbot to Agentic Workspace 

10:35 – Why ChatGPT Is Following Claude 

13:00 – The Shift from Asking to Delegating 

14:00 – What Agentic AI Actually Means for Lawyers 

17:40 – Making AI the Interface for Legal Work 

19:10 – The Future Surface of Work 

23:30 – When Your Phone Becomes Your Workspace 

25:35 – How Agentic AI Could Transform Law Firms 

26:45 – Letting AI Handle the Legal Busywork 

29:20 – Operating at the Top of Your License 

31:15 – AI Should Format the Work, Not Make the Judgment 

34:30 – How Lawyers Can Start Experimenting Safely 

37:25 – Closing Thoughts 

Privacy is not just about keeping secrets. It is about protecting your power. In episode 629 of the Lawyerist Podcast, Zack Glaser talks with Oxford professor and author Carissa Véliz about how personal data gives companies, governments, and technology platforms the ability to influence our choices and shape our lives. 

Carissa explains why seemingly harmless information, from the music you enjoy to the way your phone battery drains, can be used to identify, categorize, and predict you. They explore how AI has made surveillance cheaper and more powerful, why predictions should never be treated as facts, and how automated scores can affect important decisions without giving people a meaningful way to challenge them. 

The conversation also offers practical ways to reclaim control without abandoning technology entirely. From choosing more private digital tools to questioning the predictions presented as inevitable, Carissa shows why every decision to protect your privacy matters. 

If you have ever clicked “accept” without thinking about what happens next, this episode will change the way you think about your data, your autonomy, and who gets to shape your future. 

Listen to our previous episodes on AI, Privacy & Legal Ethics. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction 

00:55 – The Future of Law Firm Leadership 

05:00 – The Four Cornerstones of Leadership 

09:00 – Be a Next Level Leader 

10:45 – Meet Carissa Véliz 

11:45 – Why Privacy Is Power 

13:30 – How Personal Data Limits Your Autonomy 

15:50 – Who Decides What Your Data Says About You? 

17:50 – How Companies Exploit Personal Vulnerabilities 

20:10 – The Data You Never Realized Was Personal 

21:15 – The Connection Between Surveillance and Prediction 

22:30 – Applying Fiduciary Duties to Personal Data 

24:15 – Why You Cannot Contest a Prediction 

26:20 – Banning the Sale of Personal Data 

28:25 – Predictions Are Power Plays, Not Facts 

30:30 – AI and the Expansion of Digital Surveillance 

33:25 – How to Take Back Your Digital Privacy 

37:30 – Why Every Privacy Choice Matters 

40:00 – The Future Is Not Predetermined 

41:25 – The Most Private Way to Read a Book 

Law firm marketing does not have to mean paid ads, aggressive sales tactics, or posting constantly online. 

In episode 628 of the Lawyerist Podcast, Chad Fox talks with Aaron Thomas about marketing for lawyers who do not think of themselves as marketers. Aaron shares how he went from relying almost entirely on referrals to building a more intentional approach that helped grow his firm and bring in better-fit clients. 

They explore why referral marketing is still marketing, how newsletters can keep firms visible, and why useful content often works better than a direct sales pitch. Aaron also explains how lawyers can build stronger referral networks, make their expertise easier to find, and outsource repetitive marketing tasks without hiring a full-time employee. 

If you want to grow your firm without sounding salesy or turning marketing into a second job, this episode provides simple strategies you can begin using right away. 

This episode is sponsored by Posh Virtual Receptionists. As Aaron explains, effective marketing is often less about selling and more about making it easier for the right clients to find, trust, and connect with your firm. Posh helps support that experience by answering calls, improving responsiveness, and helping law firms maintain consistent communication with prospective and current clients. 

Learn more at https://posh.com/lawyerist/. 

Listen to our previous episodes on Law Firm Marketing & Building Client Relationships. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction 

00:25 – What Happens When a Business Fully Unplugs 

02:05 – Why Rest Belongs in Your Business Plan 

12:15 – Meet Aaron Thomas 

13:05 – Every Law Firm Is Already Marketing 

15:05 – Finding More of the Right Clients 

16:20 – Why Advertising Should Not Be Your First Move 

17:40 – Marketing to Your Existing Network First 

18:50 – Newsletters That Clients Want to Read 

21:05 – Networking Without the Sales Pitch 

21:55 – Creating Referral Partnerships with Other Lawyers 

23:50 – Using Helpful Content to Build Authority 

25:10 – Let Your Expertise Do the Selling 

26:25 – Why Free Information Still Leads to Paid Work 

28:30 – A Practical Starting Point for Overwhelmed Firms 

29:50 – Outsourcing the Work That Never Gets Done 

31:20 – How Basic Marketing Created Rapid Growth 

32:55 – Closing Thoughts 

Knowing your communication style is useful. Knowing when to move beyond it is what creates growth. In episode 627 of the Lawyerist Podcast, Zack Glaser talks with Zeina Baydoun about how law firm leaders and teams can use DISC to better understand themselves, communicate more effectively, and respond with greater intention. 

Zeina breaks down why DISC is not a personality test or a permanent label. It is a starting point for recognizing the behaviors that come most naturally, the blind spots those tendencies can create, and the ways stress may amplify them. Rather than using a profile to say, “That is just how I am,” she encourages leaders to ask whether their default response is actually what the person or situation needs. 

They discuss how different communication styles can create friction inside law firms, why understanding behavior can replace judgment with curiosity, and how teams can better support one another without lowering expectations for growth. 

If you want to improve communication without forcing everyone to think and work the same way, this episode offers a thoughtful framework for building more adaptable leaders and more connected teams. 

Listen to our previous episodes on Leadership, Communication & Building Stronger Law Firm Teams. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction
01:25 – Using DISC as an Active Leadership Tool
04:10 – Meet Zeina Baydoun
05:45 – What DISC Reveals About Communication
08:35 – Understanding Behavioral Preferences
12:00 – How Self-Awareness Changes Team Dynamics
14:40 – The Problem with Personality Labels
16:20 – Why Leaders Cannot Hide Behind Their Style
17:40 – Developing Skills Outside Your Comfort Zone
18:55 – Adapting Your Communication to the Situation
21:55 – Leadership and Communication Under Pressure
25:25 – Supporting Strengths and Managing Blind Spots
28:50 – Creating Space for Other People to Lead
31:05 – Moving Beyond Fixed Leadership Styles
32:10 – Building New Behavioral Habits
33:05 – Choice, Growth and Intentional Leadership
35:05 – Closing Thoughts 

Law firms deal with serious issues, but that does not mean every client interaction has to feel heavy. In episode 626 of the Lawyerist Podcast, Stephanie Everett talks with Jennifer Cargo about humor as an underrated communication skill for lawyers and law firm teams. 

Jennifer shares how her experience with comedy training and amateur standup shaped the way she connects with clients, leads a team, and lightens stressful moments inside a law firm. From breaking the ice during client signings to helping team members feel more comfortable bringing challenges to her, she explains why humor is not about being silly or unprofessional. It is about paying attention, reading the room, and making people feel at ease. 

Together, they explore how small moments of levity can build trust, improve client experience, and create a more approachable workplace culture. Jennifer also shares what comedy teaches about timing, observation, confidence, and finding the absurdity in everyday life. 

A more human law firm does not always start with a new process or platform. Sometimes, it starts with the way you make people feel when they walk through the door. 

Listen to our previous episodes on Law Firm Communication & Client Trust. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, and Instagram! 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction 

00:20 – Humor as a Serious Communication Skill 

00:45 – What Makes LabCon Different 

02:05 – Working on the Business, Not Just in It 

04:03 – Meet Jennifer Cargo 

05:17 – How Comedy School Changed Jennifer’s Perspective 

06:29 – Practicing Confidence Before the Stage 

07:22 – Standup, Improv, and Learning to Be Funny 

08:42 – Observing the Absurdity Around You 

09:05 – Turning Office Friction into Client Connection 

10:44 – Humor and the Client Experience 

12:06 – Finding Levity Without Dismissing Stress 

14:43 – Why Smiling Changes the Interaction 

15:29 – Timing, Pauses, and the Structure of a Joke 

18:56 – What Law Firms Can Learn from Comedy 

20:27 – Building Trust Through Approachable Leadership 

22:45 – AI, Comedy Writing, and Creative Prompts 

24:51 – Using AI as a Thought Partner 

25:17 – The Value of Trying Something New 

Most law firm owners know what it feels like to need help. But needing help and being ready to hire are not always the same thing. In episode 625 of the Lawyerist Podcast, Stephanie Everett sits down with Bernadette Harris to talk about the timing, planning, and clarity required to make a successful hire. 

Bernadette shares why the biggest hiring mistake is not always choosing the wrong person. Sometimes, it is hiring at the wrong time. Hire too soon, and the firm may not have enough work or revenue to support the role. Hire too late, and the owner may be too overwhelmed to train, onboard, and set the new person up for success. 

Stephanie and Bernadette discuss how to evaluate consistent demand, identify whether the owner is the real bottleneck, and use capacity planning to make a more grounded hiring decision. They also explore why lawyers need to define the role clearly before bringing someone in, including the tasks, expectations, soft skills, and success metrics that will shape the position. 

If you are thinking about hiring because your firm feels chaotic, this episode will help you pause, look at the data, and make sure you are solving the right problem before adding another person to the payroll. 

Listen to our previous episodes on Law Firm Hiring, Delegation & Building Better Teams. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps 

00:00 – Introduction
00:17 – The Case for Closing the Firm for a Week
01:30 – What Has to Be True Before You Can Unplug
02:35 – Planning Ahead So Time Off Actually Works
03:25 – Meet Bernadette Harris
03:55 – The Real Hiring Problem: Wrong Timing
04:20 – Financial Stress vs. Operational Chaos
05:25 – How to Know When Your Firm Is Ready
06:05 – Why Hiring Decisions Need Data
06:40 – Capacity Planning for Law Firm Owners
07:40 – Are People in the Right Seats?
08:45 – Consistent Work vs. One Busy Month
09:55 – The Referral Problem and Predictable Demand
11:15 – When the Owner Becomes the Bottleneck
12:25 – The Time Study Every Owner Needs
13:05 – Stop Hiring for “Help”
14:20 – Role Clarity and the Type of Person You Need
15:45 – Soft Skills Matter More Than You Think
16:40 – Why You May Need the Opposite of Yourself
17:45 – Onboarding Is More Than Paperwork
18:30 – Creating a 90-Day Training Plan
20:25 – Why Expectations Need to Be Clear Up Front
22:50 – Showing New Hires What Success Looks Like
24:30 – What Really Makes a Firm Ready to Hire
24:45 – Closing Thoughts 

AI is not just changing how lawyers work. It is changing how lawyers learn. In episode 624 of the Lawyerist Podcast, Zack Glaser talks with April Dawson, Associate Dean of Technology and Innovation and Professor of Law at North Carolina Central University School of Law, about what AI means for legal education, new lawyer training, and the future of law practice. 

April explains why law schools can no longer rely on written work alone to measure whether students truly understand the material. As AI becomes embedded in legal writing, research, and drafting tools, new lawyers will need to prove their value in different ways, including verbal explanation, critical thinking, judgment, and the ability to use technology responsibly. 

Together, they explore how AI may shrink traditional mentorship opportunities, why new lawyers need to become more self-directed learners, and how legal employers may increasingly expect graduates to arrive with real AI fluency. April also shares why small firm owners should rethink their workflows from beginning to end instead of layering AI on top of inefficient systems. 

If you are wondering what the next generation of lawyers needs to know, this episode offers a practical look at how AI is reshaping legal education, law firm training, and the skills lawyers will need to stay valuable. 

Listen to our previous episodes on AI Skills New Lawyers Need Now. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps: 

00:00 – Introduction
01:20 – What Claude for Legal Shows Lawyers About AI
05:20 – Using AI Without Starting from Scratch
09:20 – Meet April Dawson
10:40 – Why Law School Can’t Teach the Same Way
12:05 – Why Writing Alone No Longer Proves Understanding
13:20 – The Skills Clients Will Actually Measure
16:05 – Why “Strong Writer” Is Now Table Stakes
18:15 – What New Lawyers Lose When AI Does the First Draft
19:25 – How New Lawyers Can Learn Faster with AI
22:55 – Building Judgment Without 20 Years of Experience
27:10 – Why AI May Help New Lawyers Start Firms Sooner
28:35 – What Small Firms Should Rethink Before Adding AI
31:50 – Why AI-Savvy Lawyers Will Stand Out
34:15 – The Risk of Automating Broken Processes
36:15 – Closing Thoughts 

Lawyers are trained to spot risk. But when it comes to AI, focusing only on risk may cause firms to miss the bigger opportunity. In episode 623 of the Lawyerist Podcast, Zack Glaser sits down with Bridget McCormack to talk about AI arbitration, legal innovation, and why the future of legal work may be less about replacement and more about reinvention. 

Bridget reflects on her time as Chief Justice of the Michigan Supreme Court, including how the pandemic forced courts to adopt technology faster than anyone expected. She explains why that moment revealed both the limits of traditional legal systems and the potential for more accessible, user-friendly ways to resolve disputes. 

Now leading the American Arbitration Association, Bridget shares how AAA is using AI to build tools for clause drafting, self-represented parties, resolution simulation, and even documents-only arbitration. The conversation explores what fairness looks like when AI is involved, why human oversight remains essential, and how legal professionals should think about accountability, bias, and trust. 

If AI changes the routine parts of legal work, lawyers will need to rethink what clients actually need from them. This episode offers a practical and future-focused look at arbitration, legal technology, and the new kinds of judgment lawyers will need to bring to the table. 

Listen to our previous episodes on Artificial Intelligence and the Future of Legal Practice. 

Links from the episode: 

https://adr.org/ 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps: 

00:00 – Introduction 

00:55 – Why Lawyers Should Test Their Own Intake Process
03:35 – Meet Bridget McCormack
04:25 – Leading Michigan Courts Through COVID
05:20 – Why Remote Court Was Already on the Radar
06:40 – Moving Trial Courts Online Fast
08:45 – Why Legal Systems Are Slow to Change
10:33 – From Chief Justice to CEO of AAA
13:18 – How Alternative Dispute Resolution Is Evolving
14:50 – AI Tools for Arbitration and Self-Represented Parties
15:57 – Building AAA’s AI Arbitrator
17:36 – Resolution Simulation and Faster Settlements
19:05 – What Is Left for Lawyers?
21:19 – Fairness, Bias, and Human Oversight in AI Arbitration
23:45 – Why Legal Disputes Need More Options
24:41 – AI Agents and the Future of Legal Infrastructure
26:26 – When AI Agents Negotiate Contracts
28:30 – Closing Thoughts 

Most lawyers build their firms to serve clients, not to eventually leave them. But every law firm owner will exit someday, whether by choice, necessity, or life change. 

In episode 622 of the Lawyerist Podcast, Zack Glaser talks with Tom Lenfestey, attorney, CPA, and founder of The Law Practice Exchange, about why exit planning should not be treated as something reserved for retirement. Tom explains why succession planning often feels like the end, while exit planning gives firm owners more control over their future, their value, and their next act. 

They explore what makes a law firm transferable, why systems and data matter to buyers, and how lawyers can build firms that are worth more than just the owner’s name. Tom also breaks down how the market for law firm sales is changing, from private capital to alternative business structures, and why modern buyers are looking closely at financials, intake, marketing, operations, and owner independence. 

If you own a law firm, this conversation is a reminder that your firm can be more than a job you built for yourself. With the right planning, it can become an asset, a legacy, and a bridge to whatever comes next. 

Links from the episode: 
https://thelawpracticeexchange.com/ 

https://a.co/d/05rY2bUe 

Listen to our previous episodes on Law Firm Exits & Succession. 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps: 

00:00 – Introduction 

01:00 – Why Succession Planning Feels Like the End 

02:15 – Identity, Second Acts & Life After Practice 

05:00 – Meet Tom Lenfestey 

06:35 – Does a Law Firm Have Value Beyond the Owner? 

07:45 – Why Tom Started The Law Practice Exchange 

10:45 – Creating a Marketplace for Law Firm Sales 

12:55 – When to Start Planning Your Exit 

13:55 – Why Exit Planning Belongs in Your Strategic Plan 

15:45 – Why Time Is Your Biggest Advantage 

16:05 – Building a Firm with Exit in Mind 

17:30 – Why The Exit Blueprint Matters Now 

20:40 – What Law Firm Owners Need to Know Before Selling 

22:45 – Private Capital, ABS & New Buyer Models 

25:20 – What Sophisticated Buyers Want to See 

27:15 – Why Data and Systems Create Transferable Value 

29:00 – When Succession Planning Goes Wrong 

31:20 – Why Internal Successors May Not Be Buyers 

33:00 – Exit Strategy vs. Retirement Planning 

36:50 – Keeping Your Options Open After Exit 

38:50 – Where to Find The Exit Blueprint 

Hiring offshore staff can transform a law firm, but only if it's done intentionally. 

 In this episode, Zack Glaser sits down with Raquel Gomes, co-founder and CEO of Stafi, to discuss the most common mistakes law firms make when hiring remote offshore team members. Drawing on her background in psychology and experience supporting hundreds of law firms, Raquel explains why the term "virtual assistant" may be holding firms back and how successful firms build engaged, high-performing remote teams. 

Zack and Raquel explore the importance of defining roles before hiring, creating effective vetting processes, building structured onboarding systems, integrating remote staff into firm culture, and continuing to invest in team members after they are hired. They also discuss how law firm owners can move from working in the business to leading the business by building teams they trust. 

Listen to our previous episodes on hiring, delegation, leadership, and building stronger law firm teams: 

Links from the episode:  

https://getstafi.com 

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X!  

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you.  

Access more resources from Lawyerist at lawyerist.com.  

Chapters / Timestamps: 

00:00 Introduction 

01:26 Why "VA" Is the Wrong Mindset 

04:21 Mistake #1: Hiring Reactively Instead of Strategically 

06:02 Mistake #2: Weak Vetting and Screening 

09:29 How Stafi Evaluates Candidates 

11:41 Mistake #3: Poor Onboarding Processes 

13:19 Creating SOPs Through Training 

15:20 Mistake #4: Failing to Integrate Remote Staff 

18:51 Investing in Team Culture and Communication 

20:39 Mistake #5: Giving Up Too Soon 

22:58 What Makes Stafi Different 

24:45 Immigration Case Outsourcing Explained 

26:34 The Benefits of Getting Offshore Hiring Right 

27:28 Where to Learn More About Stafi