Lawyerist Podcast

Lawyers have always relied on tools—but AI is different. It doesn’t just assist with tasks; it makes decisions, applies judgment, and shapes outcomes. In episode #602 of the Lawyerist Podcast, Stephanie Everett talks with Damien Riehl about what ethical responsibility looks like when AI starts doing legal work on its own. 

Their conversation examines how AI systems embed values, why verification matters more than transparency, and how lawyers can responsibly use tools they don’t fully understand. They also explore what legal expertise looks like in an AI-powered future—and why intuition, trust, and integrity may matter more than ever as machines take over the “widgets” of legal work. 

Listen to our other episodes on Ethics and Responsibility in AI. 

EP. 582 Deepfakes, Data, and Duty: Navigating AI Ethics in Law, with Merisa Bowers Apple | Spotify | LTN 

EP. 543 What Lawyers Need to Know About the Ethics of Using AI, with Hilary Gerzhoy Apple | Spotify | LTN 

 

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 

05:55 – Meet Damien Riehl 

08:10 – Why AI Is a Different Kind of Legal Tool 

11:05 – When AI Starts Doing Legal Work 

14:30 – Ethics, Values, and AI Judgment 

18:45 – Foundation Models vs. Legal-Specific AI 

21:15 – The “Duck Test” and Trusting AI Output 

24:45 – Trust but Verify: Reviewing AI Work 

28:40 – What Lawyers Are Underestimating About AI 

31:10 – What Still Requires Human Judgment 

34:30 – Intuition, Trust, and Integrity in Law 

37:40 – What This Means for Billing and the Future 

40:40 – Closing Thoughts

Lawyers are understandably cautious about AI—but the real risk may be using it the wrong way. In episode 601 of the Lawyerist Podcast, Zack Glaser sits down with Matt Spiegel of Lawmatics to explore how agentic AI is changing the way law firms handle intake and evaluate potential clients. 

Matt breaks down why surface-level AI tools fall short, how agentic AI can make informed recommendations instead of opaque scores, and what it takes to build trust in automated decision-making. They also discuss how better intake systems can reduce wasted time, improve lead quality, and support more intentional firm growth. 

Listen to our other episodes on Artificial Intelligence in Legal Practice. 

#497: Real Talk About Artificial Intelligence in Your Office, with Ben Apple | Spotify | LTN 

#543: What Lawyers Need to Know About the Ethics of Using AI, with Hilary Gerzhoy Apple | Spotify | LTN 

#546: Unlock Law Firm Growth: AI marketing Secrets with Karin Conroy Apple | Spotify | LTN 

Links from the episode: 

https://www.lawmatics.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 

01:28 – Meet Matt Spiegel 

03:55 – From the Cloud to AI in Legal Tech 

05:38 – Why Lawyers Are Cautious About AI 

06:50 – Moving Beyond Surface-Level AI 

08:51 – Why Lead Scoring Misses the Point 

11:14 – What Makes Agentic AI Different 

14:10 – Generative AI vs. Agentic AI 

15:57 – Teaching Software to Make Decisions 

17:17 – Automating Outcomes, Not Steps 

20:10 – Why Lawmatics Was Already Agentic 

21:47 – Trust, Guardrails, and Client Data 

24:20 – What Qualify AI Does Differently 

25:33 – Closing Thoughts

Starting a law firm doesn’t automatically make you a business owner—designing one does. In episode #600 of the Lawyerist Podcast, Stephanie Everett and Zack Glaser kick off a four-part series on how to design a law firm intentionally, rather than defaulting into a business you didn’t mean to build. 

They unpack the biggest myths lawyers believe when starting a firm, why being a good lawyer isn’t enough to create a sustainable business, and how relying on personal heroics instead of structure quietly traps firm owners over time. Stephanie breaks down the three constraints that cause most firms to struggle, the three distinct paths law firms can take, and the key questions lawyers should ask early to align their business model with the life and career they actually want. 

Listen to our other episodes on Law Firm Strategy & Business Design. 

#583 – From Survival to Strategy: Scaling Your Law Firm Finances, with Bernadette Harris Apple | Spotify | LTN 

#575 – From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN 

#570 – Uncover Your Firm’s Journey with the New Small Firm Scorecard™, with Stephanie Everett Apple | Spotify | LTN 

#568 – How to Build a Law Firm You Can Sell, with Victoria L. Collier Apple | Spotify | LTN 

 

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 

01:15 – Why This Isn’t About “Starting” a Law Firm 

03:45 – The Biggest Myth Lawyers Believe About Firm Ownership 

06:50 – Heroics vs. Structure 

10:30 – The Three Constraints That Trap Law Firm Owners 

12:45 – Every Firm Is Choosing a Business Model (Whether You Realize It or Not) 

14:30 – The Three Paths Law Firms Take 

18:55 – When Your Goals and Design Don’t Match 

20:55 – How Clients Actually Buy Legal Services 

23:30 – What Breaks If Demand Doubles 

25:00 – Clarity Beats Certainty 

29:15 – What to Do in the First 30 Days 

33:40 – Where to Go Next

Law school prepares students to think like lawyers, but it often leaves them without a clear picture of what comes next. Zack Glaser sits down with Jocelyn Hardrick to explore how mentorship, pipeline programs, and practical guidance can help first-generation and nontraditional students bridge the gap between legal education and real-world practice. 

They unpack the challenges students face when they lack exposure to legal careers, the importance of writing and bar preparation support, and how community and accountability shape confidence during the transition into the profession. The episode highlights how intentional mentorship and community support can reduce uncertainty, build confidence, and create clearer pathways into the legal profession. 

Listen to our other episodes on mentorship, mindset, and professional development.  

Episode #596 — The Athlete’s Mindset for Lawyers, with Jess Sargus Apple | Spotify | LTN 

Episode #592 — Client Care, Culture, and Character: A Framework for Great Leaders, with William O’Neal Apple | Spotify | LTN 

Episode #588 — Practice Smarter, Not Harder: 411 Tips for Modern Lawyers, with Jordan Couch Apple | Spotify | LTN 

Episode #576 — How Sponsorship, Empathy, and Failure Shape Great Leaders, with Michael Cohen Apple | Spotify | LTN 

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.

Links from the episode:

https://www.journeytoesquire.com/ 

Chapters: 

00:00 – Introduction 

01:45 – Why the Path Into Law Isn’t Clear 

06:10 – Meet Jocelyn Hardrick 

08:25 – What Journey to Esquire Does 

12:40 – First-Generation and Nontraditional Barriers 

17:30 – Mentorship vs. Sponsorship 

21:55 – Writing, Bar Prep, and Practical Skills 

26:40 – Building Confidence Through Community 

31:20 – Advice for New and Aspiring Lawyers 

34:10 – Closing Thoughts

In episode #598 of the Lawyerist Podcast, learn how Microsoft Copilot can help lawyers work more efficiently inside Microsoft 365—without compromising accuracy, security, or client trust. Zack Glaser talks with Ben Schorr, innovation strategist at Affinity Consulting Group and former Microsoft insider, about how attorneys can move past AI hype and start using Copilot for real, everyday legal work. 

Zack and Ben break down how Copilot helps lawyers draft and edit documents, summarize complex files, extract key deadlines, prep for meetings, and manage inbox overload—all while keeping client data protected within Microsoft’s security framework. They clarify where Copilot delivers the most value, where caution is required, and why understanding its limitations is essential to using it effectively. For lawyers curious about AI but unsure where to begin, this episode offers a clear, realistic roadmap for adopting Copilot without compromising accuracy, ethics, or trust. 

Listen to our other episodes on  AI, Legal Technology & Practical Innovation in Law Firms:  

Rethinking Law Firm Growth in the Age of AI, with Sam Harden Apple | Spotify | LTN 

Episode 550: Beyond Content: How AI Is Changing Law Firm Marketing, with Gyi Tsakalakis & Conrad Saam Apple | Spotify | LTN 

Episode 543: AI Ethics: What Lawyers Need to Know, with Hilary Gerzhoy Apple | Spotify | LTN 

Episode 497: Real Talk About Artificial Intelligence in Your Office, with Ben Schorr Apple | Spotify | LTN 

 

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 

08:43 – Meet Ben Schorr 

11:08 – What Copilot Is (and Why Lawyers Care) 

13:27 – Security, Privacy, and Client Data 

16:47 – Drafting Legal Documents With Copilot 

18:36 – Schorr’s Law: Always Review AI Output 

20:30 – Editing, Fact-Checking, and Improving Existing Work 

23:57 – Summarizing Documents and Extracting Key Info 

28:49 – Brainstorming, Personas, and Strategy Testing 

34:34 – Agentic AI: What’s Possible (and What Isn’t)