Lawyerist Podcast

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. 

#601: Beyond Chatbots: Using Agentic AI in Law Firm Intake, with Matt Spiegel Apple | Spotify | LTN 

#590: Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN  

#587: Future-Proofing Your Firm in the Age of AI, with Jack Newton Apple | Spotify | LTN  

#575: From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox 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 – Introduction02:00 – Lawyers Lab Updates03:55 – Meet Scott Clasen05:30 – SaaS Is Dead… Or Not06:45 – Building vs Buying Legal Tech08:30 – Paying for Tools You Don’t Use09:20 – AI Isn’t Always the Answer10:45 – Context Is What Makes AI Useful13:20 – AI That Works Like a Team Member15:10 – Making Smart Tech Investments16:30 – Start with the Problem, Not the Tool18:30 – Fixing Broken Workflows 

20:10 – When AI Does More Than Your Software21:50 – Custom Software Is Back23:15 – Where Your Data Should Live25:40 – The Build vs Buy Decision27:50 – Is This a Tech Revolution?30:10 – What Will Survive in Legal Tech32:00 – Where AI Is Heading33:30 – Closing Thoughts

In episode 610 of the Lawyerist Podcast, Zack Glaser sits down with Karin Conroy to unpack why so many law firm websites fail to convert and why AI is making the problem worse. 

Karin explains why copycat marketing has always been ineffective, and how the rise of AI generated content is accelerating a wave of sameness across legal websites. As tools make it easier than ever to produce content quickly, the firms that stand out are not the ones moving faster, they are the ones thinking more strategically about differentiation, trust, and positioning. 

The conversation explores what actually matters on a modern law firm website, from messaging that resonates in seconds to branding that signals credibility to both humans and algorithms. Zack and Karin also break down where AI fits into a smart marketing strategy and where it quietly undermines it. 

If your website looks good but is not bringing in clients, this episode will help you rethink what “working” really means. 

Listen to our previous episodes on law firm marketing with Karin Conroy:   

#603: Turn Expertise into Clients: Building Authority That AI Recognizes, with Karin Conroy Apple | Spotify | LTN 

#584: How to Stay Human in the Age of AI-driven Law Firm Marketing, with Creative Conroy Apple | Spotify | LTN  

#559: The Imitation Trap: Lessons from 15 Years of Top Law Firm Websites , with Conroy Creative Counsel (Sponsored) Apple | Spotify | LTN   

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

Links from the episode: 

https://www.conroycreativecounsel.com/lawyerist/

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 – Meet Karin Conroy 

03:45 – The Problem with Copycat Websites 

06:00 – Why “Inspiration” Turns Into Sameness 

08:30 – AI Slop Before AI 

10:30 – If You Look the Same, You Compete on Price 

12:30 – What Your Website Should Actually Do 

14:30 – The 3 Second Rule 

16:00 – Messaging That Makes Clients Feel Understood 

18:30 – Stock Photos and Fake AI Images 

21:00 – Using AI Without Killing Your Brand 

24:00 – Why Most Bio Pages Fail 

27:00 – What Clients Actually Care About 

29:30 – Trust Signals That Matter 

32:00 – Content Is Cheap, Expertise Is Not 

35:00 – How to Stand Out in a Sea of Sameness 

38:00 – The Only Shortcut That Works 

41:00 – Closing Thoughts

Most law firms are designed for lawyers, not clients. And clients feel it. In episode 609 of the Lawyerist Podcast, Stephanie Everett sits down with Laura Hartnett to explore how design thinking can transform the way legal services are delivered. 

Laura breaks down why clients often feel confused, anxious, or left in the dark, even when lawyers are doing excellent work. She shares how small changes, like rethinking communication, mapping the client journey, and understanding what happens after you deliver advice, can dramatically improve both client satisfaction and firm efficiency. 

Together, they share practical ways to rethink your processes, clarify your communication, and deliver work clients can actually understand and use. If you want to build a law firm that feels clearer, more human, and easier to work with, this episode offers a smarter approach to designing your practice. 

Listen to our previous episodes on Client Experience & Designing Better Legal Services. 

#606: Breaking the Copycat Cycle: Building a Law Firm with Personality, with Patrick Patino Apple | Spotify | LTN 

#600: Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN 

#597: What Lawyers Get Wrong About Teaching Clients and Teams, with Danielle Hall Apple | Spotify | LTN 

#462: Designing an Empathetic Client Experience, with Kirk Simoneau Apple | Spotify | LTN 

 

Links from the episode: 

https://laurahartnett.com/ 

https://lawyerist.com/turn-ai-into-your-small-firms-advantage/ 

 

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 Laura Hartnett 

05:00 – What “Design Thinking” Actually Means 

06:05 – Why Client Experience Starts with Emotion 

07:45 – Stop Inheriting Your Law Firm 

08:40 – Where to Start: Understanding Your Client 

10:20 – Mapping the Client Journey 

12:15 – The Hidden Friction in Law Firm Processes 

14:30 – Why Clients Don’t Understand Your Work 

16:25 – Designing Deliverables Clients Can Use 

18:20 – Lessons from Other Industries 

19:05 – AI, Client Expectations & New Behaviors 

21:40 – Teaching Clients When to Call You 

23:00 – Redesigning Legal Services for the Future 

25:00 – Staying Curious About AI & Change 

27:00 – Closing Thoughts

In episode 608 of the Lawyerist Podcast, Stephanie Everett talks with former Big Law business development professional Megan Senese about the human side of legal marketing and why the most effective client development strategies often look less like selling and more like genuine connection. 

For many lawyers, business development feels awkward, performative, and disconnected from the real work of practicing law. Megan challenges that assumption by showing how meaningful relationships, not sales tactics, are what actually drive sustainable growth. 

They explore why traditional networking advice fails so many lawyers, how small thoughtful gestures can build stronger professional relationships, and why authenticity matters more than ever in a crowded legal marketplace. Megan also shares practical ideas for nurturing relationships, staying top of mind without being transactional, and approaching business development in a way that feels natural rather than forced. 

If the idea of “doing marketing” makes you cringe, this episode offers a more sustainable approach to building relationships, trust, and ultimately a thriving legal practice. 

Listen to our previous episodes on Law Firm Marketing & Differentiation. 

#606: Breaking the Copycat Cycle: Building a Law Firm with Personality, with Patrick Patino Apple | Spotify | LTN 

#580: Smarter Law Firm Marketing: AI Tools That Actually Work, with FirmPilot Apple | Spotify | LTN 

#550: Beyond Content: How AI is Changing Law Firm Marketing, with Gyi Tsakalakis and Conrad Saam Apple | Spotify | LTN 

#549: A Journey into Video Marketing, with Temi Siyanbade Apple | Spotify | LTN 

#515: Simple Marketing Hacks Lawyers Swear By, with Gyi Tsakalakis Apple | Spotify | LTN

 

Links from the episode:

https://stage.guide  

 

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 

02:05 – Why Thoughtful Gestures Strengthen Professional Relationships 

05:10 – Meet Megan Senese 

06:25 – Why Business Development Feels So Hard for Lawyers 

07:10 – How to Make Networking Feel Natural 

09:20 – Why Copying Other Firms’ Marketing Doesn’t Work 

10:15 – Turning Personal Interests into Business Development 

12:30 – Simple Ways to Nurture Professional Relationships 

14:00 – Staying Top of Mind Without Being Salesy 

15:10 – How Long It Actually Takes to Build Client Relationships 

16:05 – How to Ask for Business Without Feeling Awkward 

18:05 – Why Listening Creates Better Pitch Opportunities 

20:00 – Staying Curious About New Tools and Technology 

23:00 – Closing Thoughts

AI is more than just another tool for lawyers. It may fundamentally change how law firms make money. In episode #607 of the Lawyerist Podcast, Stephanie Everett talks with legal industry analyst Jordan Furlong about the shifting economics of law practice and what happens as AI begins doing work lawyers once billed for. 

Jordan explains why the traditional law firm model built on billable hours and human effort is starting to break down as legal workflows become automated. Together, they explore how AI may shift lawyers away from producing legal work and toward supervising systems, validating outcomes, and delivering the one thing machines cannot easily replicate: judgment under uncertainty. 

The future of law practice may depend less on expertise and more on qualities machines struggle to replicate such as judgment, character, and the ability to guide clients through uncertainty. The conversation also explores why hourly billing may no longer make sense in an AI-driven world, how firms can rethink pricing around outcomes and client experience, and why smaller firms may adapt more quickly. 

If the billable hour fades and AI begins handling the routine “widgets” of legal work, the real question becomes what a lawyer’s value is now, and how firms should prepare for what comes next. 

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

#601 – Beyond Chatbots: Using Agentic AI in Law Firm Intake, with Matt Spiegel Apple | Spotify | LTN 

#590 – Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN 

#587 – Future-Proofing Your Firm in the Age of AI, with Jack Newton Apple | Spotify | LTN 

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

Links from the episode: 

https://jordanfurlong.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 

01:45 – Why Everyone Is Talking About AI in Law 

04:20 – Meet Jordan Furlong 

06:40 – The Real Disruption AI Brings to Law Firms 

09:30 – The Economics Behind the Billable Hour 

12:50 – What Happens When Software Does the Work 

16:05 – The Shift from Expertise to Judgment 

19:20 – What Lawyers Still Do Better Than AI 

22:40 – Client Value in an AI-Driven Profession 

26:00 – Why Smaller Firms May Have an Advantage 

29:10 – What This Means for New Lawyers 

32:45 – Preparing for the Next Version of Law Practice 

36:10 – Closing Thoughts