Lawyerist Podcast

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:   

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. 

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. 

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. 

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 

Standing out in a crowded legal market requires more than competence. It requires intentional client experience. In episode 606 of the Lawyerist Podcast, Zack Glaser talks with Patrick Patino about redefining professionalism and building a law firm people actually want to work with. 

Patrick shares how he walked away from a successful bankruptcy practice to experiment with a more human-centered model focused on connection, accessibility, and community. They examine why most firms look and feel the same, how experience shapes client loyalty, and why fear-based marketing quietly undermines trust. 

If you are questioning the traditional law firm playbook, this episode offers concrete ways to attract better clients, clarify your positioning, and design a firm that fits both your values and your market. 

Links from the episode:

https://podcasts.apple.com/us/podcast/the-newfangled-lawyer/id1699645225

Listen to our previous episodes on Client Experience & Law Firm Differentiation. 

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 – Discipline Is Boring Until Results Show Up 

07:05 – Meet Patrick Patino 

09:30 – Rethinking Professionalism 

11:15 – High Five Legal and the Bankruptcy Experiment 

13:30 – Fear Based Marketing vs. Levity 

16:10 – Meeting Clients Where They Are 

18:45 – Community Over Sales Pitches 

20:50 – The Copycat Law Firm Problem 

23:30 – Experience Is the Differentiator 

26:05 – The Crumbl Cookie Model of Law 

28:40 – Scaling Culture with the Pod Model 

31:15 – Talking With Clients, Not At Them 

34:00 – Collaboration Over Control 

36:20 – Define Your Ideal Client for Real 

38:45 – Solo and Small Firm Advantage 

41:20 – What It Means to Be Newfangled 

In episode 604 of Lawyerist Podcast, Stephanie Everett sits down with Andy Hays to explore the shift from solo practitioner to true business owner. After nearly two decades of firm ownership, Andy shares why he recently rebranded to remove his personal name from the firm, a strategic move designed to reduce dependency on him and strengthen the firm’s future. 

They discuss delegation, hiring before you feel fully ready, automating repetitive processes, and setting clear expectations for team performance. The conversation also dives into accountability, leadership growth, and how small operational improvements compound over time. 

If you are ready to move beyond founder dependence and build a firm designed for scalability, resilience, and long-term value, this episode offers practical frameworks and real-world insight to help you get there. 

Listen to our previous episodes on Scaling & Building a Sellable Firm. 

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 

03:50 – Standards, KPIs & Hard Conversations 

07:30 – Meet Andy 

08:45 – Lessons from 18 Years in Practice 

10:15 – Removing Your Name from the Firm 

12:45 – Building a Firm You Can Sell 

15:30 – Automation & Low Hanging Fruit 

17:00 – Accountability & Team Meetings 

19:25 – The “I’ll Just Do It Myself” Trap 

21:15 – Hiring Strategically 

23:30 – Expanding the Physical Office 

25:40 – Closing Thoughts 

In episode 604 of Lawyerist Podcast, discover how addressing alcohol and mental health can unlock greater clarity, confidence, and long-term success in your legal career. Stephanie Everett sits down with IP attorney and recovery coach Melissa Silverstein to talk about alcohol, achievement, and the hidden pressures inside the legal profession. 

Melissa shares her personal journey from high-achieving “functioning” lawyer to long-term sobriety, and explains why so many attorneys struggle silently while still appearing successful on the outside. Together, they explore law firm drinking culture, client expectations, stigma around asking for help, and why recovery does not have to mean labels or all-or-nothing thinking. 

If you’ve ever felt burned out, anxious, or not quite like your best self, this episode offers practical insight, reassurance, and a path toward building a healthier, more sustainable legal career without shame. 

Listen to our previous episodes on Lawyer Well Being & Recovery. 

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 – Intro & Conference Recap 

08:30 – Melissa’s Story 

10:00 – Achievement as a Mask 

12:10 – Rethinking Abstinence 

14:30 – Harm Reduction & Personal Choice 

15:50 – Warning Signs in Law Practice 

16:30 – The Role of the Bar 

17:50 – Leadership & Language 

20:00 – Rethinking Firm Events 

23:10 – Career Growth After Recovery 

26:00 – De-Stigmatizing Help 

29:00 – Closing Thoughts 

In episode 603 of Lawyerist Podcast, Zack Glaser sits down with Karin Conroy to examine how AI is changing the rules of law firm marketing and what that means for lawyers who want to stand out for the right reasons.  

Karin explains why expertise, not automation, is what rises to the top in an AI filtered world. As large language models reshape how potential clients search for answers, shortcuts like keyword stuffing and mass produced content are quickly losing their impact. What stands out instead is real authority built through credibility, third party validation, media appearances, and consistent messaging across platforms. 

The conversation also challenges the idea that your website is your first impression. In today’s landscape, visibility often starts elsewhere. Zack and Karin unpack how referral systems support a larger authority strategy and what it truly means to move from building, to stabilizing, to growing your marketing in a deliberate and sustainable way. 

Listen to our previous episodes with Karin:  

Links from the episode: 

https://conroycreativecounsel.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 – Meet Karin Conroy
02:30 – AI, Agents & The Content Explosion
04:15 – The M Dash as a Trust Tell
07:00 – Why Google Isn’t the Front Door Anymore
09:00 – Knowledge Panels & Online Authority
12:30 – You Can’t Fake Expertise
15:00 – Stop Chasing SEO Tricks
17:30 – Authority Through Media & PR
21:00 – Who Needs a Media Kit
23:00 – Referrals Are a Marketing Strategy
25:00 – Build Before You Scale
28:00 – AI Rewards Real Experts
32:30 – Closing Thoughts 

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. 

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. 

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