Choosing the Right Legal Tech in the Age of AI, with Scott Clasen

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

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.  #603 – Turn Expertise into Clients: Building Authority That AI Recognizes, with Karin Conroy Apple | Spotify | LTN  #600 – Designing a Law Firm You Actually Want to Run, with Stephanie Everett Apple | Spotify | LTN  #575 – From Overwhelmed Lawyer to Strategic Law Firm Owner, with Chad Fox Apple | Spotify | LTN  #559 – The Imitation Trap: Lessons from 15 Years of Top Law Firm Websites, with Conroy Creative Counsel 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 – 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.  #306: Getting to Know & Love Your Numbers, with Bernadette Harris Apple | Spotify | LTN  #583: From Survival to Strategy: Scaling Your Law Firm Finances, with Bernadette Harris Apple | Spotify | LTN  #588: Practice Smarter, Not Harder: 411 Tips for Modern Lawyers, with Jordan Couch 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  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.  469: Lawyers in Crisis: Navigating Addiction and Mental Healthy, with Brian Cuban Apple | Spotify | LTN  #477 Controlling Alcohol with Annie Grace Apple | Spotify | LTN  #506: Managing Stress & Avoiding Burnout, with Emily Nagoski Apple | Spotify | LTN  #533 The Alcohol Experiment, with Annie Grace Apple | Spotify | LTN  #535 Lawyer Burnout: 5 Hidden Signs You’re About to Crash, with Natasha Evans 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 – 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:   #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   #584: How to Stay Human in the Age of AI-driven Law Firm Marketing, with Creative Conroy Apple | Spotify | LTN      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 Conroy02:30 – AI, Agents & The Content Explosion04:15 – The M Dash as a Trust Tell07:00 – Why Google Isn’t the Front Door Anymore09:00 – Knowledge Panels & Online Authority12:30 – You Can’t Fake Expertise15:00 – Stop Chasing SEO Tricks17:30 – Authority Through Media & PR21:00 – Who Needs a Media Kit23:00 – Referrals Are a Marketing Strategy25:00 – Build Before You Scale28:00 – AI Rewards Real Experts32:30 – 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.  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