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 

Claude for Legal is not just something lawyers can install and use out of the box. It is a starting point for building smarter, more intentional law firm workflows. 

In this follow-up to last week’s conversation, Zack Glaser continues his discussion with Sam Harden about Claude for Legal, AI skills, and what law firms need to understand before adding automation into their work. Sam explains why lawyers should not treat Claude’s legal plugin as a finished product, but as a framework they can customize around their own processes, practice areas, and firm strategy. 

They discuss how lawyers can modify AI skills, share them across a team, avoid creating more silos, and think through workflows before automating them. From demand letters to deposition summaries to safe experimentation, this episode explores how AI can help lawyers reduce repetitive work while preserving the judgment, expertise, and “secret sauce” that make their firms valuable. 

Listen to our previous episodes on Artificial intelligence, law firm workflows, and the future of legal practice: 

Links from the episode: 

Posh.com/lawyerist 

https://samharden.substack.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
00:20: Why “Ready” Can Be Fear in Disguise
05:14: Sponsor Conversation with Posh
13:16: What Claude for Legal Actually Is
15:04: Claude for Legal 2.0
17:28: The Risk of Non Lawyers Using Legal AI
20:09: What This Means for Attorneys
21:17: The Plugin Is Not the Plan
23:22: Customizing Claude for Your Practice  

27:20: Sharing AI Skills Across a Firm
29:03: Why Law Firms Need an AI Strategy
31:19: Map Workflows Before Automating 

33:05: Connecting AI to Your Firm’s Data
39:13: How Far Can Law Firm AI Go?
42:54: Practicing at the Top of Your License
43:31: Safe AI Experimentation for Lawyers 

47:44: Where to Find Sam Harden 

Claude is not just another AI tool lawyers can chat with. It may be a preview of where legal work is heading. In episode 619 of the Lawyerist Podcast, Zack Glaser talks with Sam Harden about Claude, Claude for legal, and the growing role of AI in law firm workflows. 

Sam breaks down how Claude can work with documents, folders, PDFs, Word files, and connected legal tools in ways that go far beyond simple prompting. They discuss the difference between Claude Chat, Claude Cowork, connectors, and skills, and why those distinctions matter for lawyers trying to understand what AI can actually do. 

They also explore why law firms should not rush into automation without first building better systems. From deposition summaries to document creation to legal research support, this episode explains how AI can become more useful when it is guided by strong processes, clear instructions, and thoughtful implementation. 

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

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 

00:34 – Why Claude for Legal Matters 

01:28 – Live Crabs and Work from Home Chaos 

07:04 – Setting Up the Conversation 

07:29 – Meet Sam Harden 

08:04 – What Lawyers Should Watch with Claude 

10:14 – What Claude Actually Is 

11:16 – How AI Moved Beyond Chat 

12:07 – From Claude Code to Claude Cowork 

13:22 – How Claude Works with Documents 

15:20 – Why Claude Cowork Is a Big Shift 

15:45 – Creating Documents and Presentations 

16:52 – Claude Chat vs. Cowork vs. Code 

18:12 – Legal Plugins and Connectors 

19:30 – Reducing Context Switching with AI 

20:49 – Connecting Claude to Legal Tools 

22:24 – What Legal Connectors Can Do 

24:47 – MCP, Tools, and Connector Limits 

26:37 – What Claude Skills Are 

28:44 – Why SOPs Come Before AI Skills 

29:43 – Using Skills for Legal Documents 

30:35 – AI Skills for Deposition Summaries 

31:14 – Combining Connectors and Skills 

32:15 – Teaching Claude Like a Team Member 

33:11 – Choosing the Right Skill 

34:00 – How Bad Instructions Create AI Risk 

35:49 – Building Better Skills and Plugins 

37:13 – What Comes Next for Claude for Legal 

Wrongful convictions and AI privacy may seem like separate issues, but both raise the same uncomfortable question: what happens when the legal system relies on old assumptions in a changing world? In episode 618 of the Lawyerist Podcast, Zack Glaser talks with Sunny Eaton about conviction review work, evolving science, and why lawyers should not be so quick to surrender privacy expectations in the age of AI. 

Sunny shares how her work in the Nashville District Attorney’s Office focuses on reviewing old convictions, identifying new evidence, and helping correct cases where the system may have gotten it wrong. She explains why changing science, including advances in DNA, trauma research, and bias studies, can matter deeply when reviewing criminal convictions. 

The conversation then turns to AI, attorney client privilege, client data, and the growing role of data brokers. Zack and Sunny explore whether information shared with AI tools should automatically lose privacy protection, and why lawyers may need to make stronger arguments before courts accept that assumption. 

If you are concerned about AI in law firms, client confidentiality, or the future of privacy rights, this episode challenges lawyers to think harder about what should remain private and why it is our job to make the government work for it.  

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 

01:25 Pruning Your Practice 

04:15 When Loyalty Gets in the Way 

06:25 Meet Sunny Eaton 

08:45 Conviction Review Units 

09:50 Reviewing Old Cases 

11:25 Building Trust 

12:40 What Cases Qualify 

14:35 Changing Science 

16:00 DNA, Trauma, and Bias 

18:05 Case by Case Review 

19:25 Bad Science and Old Convictions 

20:40 AI and Privacy 

22:00 Lawyers, Therapists, and Privacy 

23:20 Giving Up Too Quickly on AI Privacy 

25:30 Reasonable Expectations of Privacy 

26:15 Client Data and AI Risk 

29:15 What Email Teaches Us 

31:00 Attorney Client Privilege and AI 

33:20 Personal vs. Workplace AI Use 

34:00 Old Rules, New Technology 

35:45 Make the Government Work for It 

AI is changing legal marketing faster than most law firms realize. In episode 617 of the Lawyerist Podcast, Stephanie Everett talks with Conrad Saam, founder of Mockingbird, about what law firms need to understand as AI begins reshaping marketing, reporting, decision making, and the business of running a firm. 

Conrad shares why AI may give smaller, more entrepreneurial law firms a new way to compete against larger firms with bigger budgets and more data. He explains how firms can use AI to build smarter internal systems, improve reporting, and rethink the tools they rely on every day. 

The conversation also explores leadership under pressure through Conrad’s volunteer work in ski patrol and search and rescue. From staying calm in high stress situations to debriefing after things go wrong, he shares practical lessons law firm owners can apply when managing clients, teams, campaigns, and business decisions. 

If you are trying to understand what AI really means for law firm growth, legal marketing, and the future of small firms, this episode offers a grounded look at what is changing, what is overhyped, and what law firm owners should pay attention to next. 

Listen to our previous episodes on Legal Marketing, AI & Smarter Law Firm Growth. 

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 – Lawyer Mental Health and Well Being
02:45 – Meet Legal Marketing Expert Conrad Saam
03:35 – The Early Days of SEO for Lawyers
04:00 – What Search and Rescue Teaches About Business
06:40 – Why Law Firm Owners Struggle to Disconnect
08:45 – Calm Leadership in Stressful Moments
09:55 – How Leaders Shape Law Firm Culture
12:05 – Using Checklists to Make Better Business Decisions
13:00 – Preparing for Problems Before They Happen
14:20 – Why Outcomes Don’t Tell the Whole Story
16:05 – The Value of Legal Marketing Content
17:40 – AI and the Future of Legal Marketing
18:25 – What ABA Tech Show Revealed About AI
19:35 – Why Law Firms May Build Their Own AI Tools
20:35 – Can AI Level the Playing Field for Small Firms?
23:35 – Replacing Expensive Reporting Systems with AI
26:25 – Why AI Rankings Can Be Misleading
28:45 – Tactical Marketing for Law Firm Owners
31:10 – Rethinking Leadership as a Law Firm CEO
32:20 – Closing Thoughts 

Many lawyers know they need to delegate. Far fewer actually do it in a way that leads to real growth. In episode 616 of the Lawyerist Podcast, Chad Fox sits down with Ellen Williamson to explore what it looks like to build a law firm that doesn’t rely on you for every decision. 

Ellen breaks down the mindset shift from being the person who does the work to the person who leads it. She shares how she moved from handling every task herself to creating systems, training her team, and trusting others to take ownership of client work. 

The conversation also explores why delegation can feel inefficient in the short term, how to think about the long-term payoff, and what it takes to build a team that can think, not just execute. 

If you want to scale your firm without burning out or becoming the constant bottleneck, this episode offers a clearer way to approach delegation, leadership, and sustainable growth. 

Listen to our previous episodes on Law Firm Growth, Delegation & Leadership. 

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 

04:20 – Meet Ellen Williamson 

05:30 – You Might Be the Bottleneck 

07:00 – Why Doing Everything Feels Easier 

09:00 – The Hidden Cost of “I’ll Just Do It” 

11:10 – Why Delegation Feels Inefficient 

13:00 – Sticking With It Long Enough to Scale 

15:00 – How to Train People to Think Like You 

17:20 – Turning One Task Into a Repeatable System 

19:10 – The $500 vs. $50 Task Shift 

21:00 – Using Video to Transfer Knowledge 

23:00 – When Your Team Starts Thinking for You 

25:00 – Structuring Time to Avoid Constant Interruptions 

27:00 – Rethinking Billing and Incentives 

29:00 – Letting Go of Control (For Real) 

31:00 – Becoming the CEO of Your Firm 

33:00 – What Growth Actually Looks Like 

35:00 – Closing Thoughts 

What happens when the best lawyer in the office becomes the boss? In episode 615 of the Lawyerist Podcast, Zack Glaser sits down with Debbie Foster and Stephanie Everett to talk about the leadership gap inside most law firms and why technical skill does not automatically translate into great leadership. 

They explore why so many firms rely on “figure it out as you go” leadership, how that creates burnout and frustration, and why so many leaders end up becoming the bottleneck in their own business. 

Debbie and Stephanie introduce their four leadership cornerstones and explain how law firm leaders can shift from solving every problem themselves to creating teams, systems, and workflows that work without constant intervention. 

If you are tired of putting out fires all day, this episode is your reminder that leadership should feel more strategic and a lot less exhausting. 

Listen to our previous episodes on Law Firm Leadership & Building Better Teams. 

Links from the episode: 

https://beanextlevelleader.com/ 

Chapters / Timestamps: 

00:00 – Introduction 

00:30 – Using AI as a Thought Partner 

02:00 – Better Prompts, Better Leadership Decisions 

05:30 – Meet Debbie Foster and Stephanie Everett 

06:40 – What Are Next Level Leaders? 

08:15 – Why Most Law Firms Don’t Train Leaders 

10:05 – Learning Leadership the Hard Way 

12:10 – The Four Cornerstones of Leadership 

17:20 – From Heroics to Architecture 

18:45 – Why Leaders Become the Bottleneck 

20:10 – From Problem Solver to Multiplier 

21:30 – Building Sustainable Leadership Systems 

23:00 – Who This Program Is For 

25:30 – The Book, Workbook, and Leadership Cohorts 

28:00 – Leadership Is a Skill, Not a Title 

29:00 – Closing Thoughts