Lawyerist Podcast

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 

Most law firm owners are highly strategic in their legal work, but far less intentional about their finances. And it shows up at tax time. 

In episode 614 of the Lawyerist Podcast, Bernadette Harris talks with Jayden Doye about the financial habits that quietly cost law firms thousands and why reactive tax preparation is not the same as real tax strategy. 

Jayden breaks down the key differences between bookkeeping, tax preparation, and tax planning, and explains why many lawyers overpay the IRS simply because they wait too long to act. They also explore common mistakes like misclassifying employees, relying on DIY accounting, and focusing on revenue instead of profit. 

Together, they share practical ways to take control of your numbers, build better financial systems, and make smarter decisions throughout the year, not just in April. 

If you want to stop guessing, reduce your tax burden, and run a more financially stable firm, this episode offers a more proactive approach to managing your practice. 

Listen to our previous episodes on Law Firm Profitability & Financial Clarity. 

Links from the episode: 

https://theelawfirmcpa.com/home 

Chapters / Timestamps: 

00:00 – Introduction
02:15 – Why Perfectionism Holds Lawyers Back
08:10 – Meet Jayden Doye
09:00 – The #1 Tax Mistake Law Firms Make
10:45 – Why Doing It Yourself Costs More
12:20 – Understanding the Financial Basics
15:00 – How to Actually Lower Your Tax Bill
17:00 – The Hiring Mistake That Can Trigger Audits
19:00 – Are You Paying Yourself the Right Way?
21:45 – Revenue vs. Profit (What Actually Matters)
23:30 – Why Tax Bills Catch Lawyers Off Guard
25:30 – Fixing the Problem Moving Forward
26:40 – Simple Habits for Better Financial Control
28:10 – The One Rule Every CPA Agrees On 

Access to justice is not just a gap. It is a scale problem. In episode 613 of the Lawyerist Podcast, Zack Glaser talks with Zach Zarnow, Executive Director of Scale Justice, about what it really takes to reach more people without relying on more lawyers. 

Zach explains why traditional approaches like pro bono work, while valuable, are not enough to meet the overwhelming demand for legal help. Instead, Scale Justice focuses on building systems, tools, and partnerships that expand the reach of legal services through technology and collaboration. 

They explore how courts, legal aid organizations, and community groups can work together to meet people earlier in their legal journeys, why designing for real user needs matters more than ever, and how thoughtful use of technology can increase impact without sacrificing quality. 

If you are thinking about how to serve more clients, build more efficient systems, or rethink the role of your firm in a larger ecosystem, this episode offers a broader and more scalable way to approach legal services. 

Listen to our previous episodes on Access to Justice, Technology & Scaling Legal Help. 

Links from the episode: 

www.scalejustice.org 

Check out the episode on YouTube: https://youtu.be/4A3J-UjAdjQ 

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 

04:40 – Meet Zach Zarnow 

06:20 – The Access to Justice Problem 

07:50 – Why More Lawyers Isn’t the Answer 

09:15 – Building Systems That Actually Scale 

11:10 – Partnering Instead of Selling 

12:30 – What It Means to Be Mission-Driven 

14:00 – Where the Courts Fit In 

15:30 – Solving Legal Problems Before They Escalate 

17:00 – Catching Legal Issues Early 

18:20 – Technology as a Force Multiplier 

19:10 – The Risks of DIY Legal AI 

21:05 – Who Should (and Shouldn’t) Use These Tools 

22:45 – Why Most Legal Tech Should Be Treated as an Experiment 

23:50 – What the Future Could Look Like 

25:00 – Ways Lawyers Can Contribute 

26:30 – Closing Thoughts 

AI is not just another tool. It is changing how clients think, act, and make decisions. In episode 612 of the Lawyerist Podcast, Stephanie Everett talks with Cat Casey about what lawyers need to understand before AI creates problems they cannot fix. 

As more clients turn to tools like ChatGPT, lawyers are facing new challenges around trust, accuracy, and confidentiality. Cat explains why even lawyers who choose not to use AI still need to understand it, and how failing to do so can create real risks for both lawyers and their clients. 

They share practical ways to approach AI with the right mindset, including how to think about its limitations, how to use it as a thinking partner instead of a replacement, and how to guide clients who may not understand the consequences of using it. 

If you want to stay ahead of where the legal profession is heading, this episode offers a clear and actionable place to start. 

Listen to our previous episodes on Using AI in Law Practice. 

Links from the episode: 

 https://thetechnocat.com/about 

Check out the episode on YouTube:

https://youtu.be/PQwAxiNjbhY

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 

02:10 – A New Way of Working with AI 

05:00 – From Task Execution to Orchestration 

07:45 – Meet Cat Casey 
09:30 – The Shift Happening Right Now in Law 
11:15 – The Rise of AI in Client Behavior 
13:45 – Understanding AI Without Getting Technical 
16:35 – Why AI Is Not a Research Tool Replacement 
18:50 – The Role of Judgment in an AI World 
20:10 – AI as a Collaborative Tool 
22:10 – Why Iteration Is Part of the Process 
23:25 – When AI Creates Legal Risk 
25:55 – Confidentiality and Privilege in Practice 
27:10 – The Reality of Discoverability 
28:20 – Lessons from Past Tech Shifts 
29:30 – Where Lawyers Should Start 

Most law firms don’t have a tech problem. They have a decision-making problem. 

In episode 611 of the Lawyerist Podcast, Zack Glaser talks with Scott Clasen about how to evaluate legal technology in a world where AI is changing everything and somehow making it more confusing at the same time. 

Too many firms are stuck buying more tools, chasing new features, and hoping the next platform will finally fix their workflow. Scott challenges that approach by shifting the focus away from software and back to systems, asking a more important question: what problem are you actually trying to solve? 

They explore the rise of AI-powered SaaS, the appeal of building your own tools, and why “AI-enabled” doesn’t always mean “useful.” The conversation also breaks down how to evaluate legal tech vendors, what contextual AI actually means, and how to think about long-term investments when the landscape keeps shifting every six months. 

If your tech stack feels bloated, expensive, or underwhelming, this episode offers a smarter way to make decisions that actually move your firm forward. 

Listen to our previous episodes on Legal Tech, AI, and Smarter Law Firm Systems. 

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
02:00 – Lawyers Lab Updates
03:55 – Meet Scott Clasen
05:30 – SaaS Is Dead… Or Not
06:45 – Building vs Buying Legal Tech
08:30 – Paying for Tools You Don’t Use
09:20 – AI Isn’t Always the Answer
10:45 – Context Is What Makes AI Useful
13:20 – AI That Works Like a Team Member
15:10 – Making Smart Tech Investments
16:30 – Start with the Problem, Not the Tool
18:30 – Fixing Broken Workflows 

20:10 – When AI Does More Than Your Software
21:50 – Custom Software Is Back
23:15 – Where Your Data Should Live
25:40 – The Build vs Buy Decision
27:50 – Is This a Tech Revolution?
30:10 – What Will Survive in Legal Tech
32:00 – Where AI Is Heading
33:30 – Closing Thoughts