Shows / AI Tools for Practicing Lawyers
AI Tools for Practicing Lawyers
AI Tools for Practicing Lawyers delivers practical, no-nonsense guidance on how attorneys can use artificial intelligence tools in their law practices — right now.
This podcast is for practicing lawyers who want real-world answers, not hype.
Each episode focuses on clear, understandable explanations of AI tools that can help attorneys work more efficiently, communicate more effectively, and make better business decisions — without requiring technical expertise or coding knowledge.
We cover…
Episodes
- AI Tools for Practicing Lawyers
Episode 034 Jane Jetson’s Book Club and the Demise of Prompting
SHOW NOTES Students in 2026 can't imagine writing a ten-page paper without ChatGPT. Judges are split between refusing to touch AI and quietly using it to…
- AI Tools for Practicing Lawyers
Episode 033 The AI Has Left The Building
SHOW NOTES Every AI tool lawyers use was trained on the whole internet, including the good sites, the bad ones, and the ones that say the moon landing was…
- AI Tools for Practicing Lawyers
AI Builds: How Secure is Google?
SHOW NOTES Your clients' bank statements, tax returns, and credit reports may already live on Google's servers. Gmail, Drive, Docs, and now Gemini. Google…
- AI Tools for Practicing Lawyers
AI Builds: How Secure is Microsoft?
SHOW NOTES Your email is in Outlook. Your briefs are in Word. Your client files sit in SharePoint and OneDrive. Now Microsoft wants to put Copilot in the…
- AI Tools for Practicing Lawyers
Field Note: Which is More Secure, Google or Microsoft?
SHOW NOTES Google or Microsoft? Most lawyers treat that as a question about Outlook versus Gmail. It isn't. It's a question about who protects your clients'…
- AI Tools for Practicing Lawyers
Episode 032 Workflow Options: BK Fastlane
SHOW NOTES Every vendor at next year's bankruptcy conventions will say their product "uses AI." The better question is what the AI is actually allowed to do…
- AI Tools for Practicing Lawyers
Episode 031 AI and Access to Justice
SHOW NOTES Maryland has about 40,000 lawyers. Roughly half a percent of them work in civil legal aid. Add more lawyers and you still hit a ceiling, because…
- AI Tools for Practicing Lawyers
Field Note: Materials from NACBA's "Me, Myself & AI" Webinar
SHOW NOTES Every CLE season produces a stack of materials that make sense in the room and mean nothing six months later. NACBA's "Me, Myself, and AI" program…
- AI Tools for Practicing Lawyers
Episode 030 Workflow Options: Irys
SHOW NOTES Lawyers are building Claude skills, custom GPTs, and homegrown intake bots faster than ever. Most of what they're building will be obsolete in six…
- AI Tools for Practicing Lawyers
Episode 029 AI and the Rise of the Superpowered Solo
SHOW NOTES Every lawyer who's ever complained that no software vendor understands their practice has secretly wondered the same thing Tara Salinas actually did…
- AI Tools for Practicing Lawyers
Episode 028 AI Skills and the $1500 Divorce
SHOW NOTES A legal industry business professional spends her career building expertise, then watches AI automate the most valuable parts of that work. That's…
- AI Tools for Practicing Lawyers
Episode 027 Is it Safe to Go to the Rave?
SHOW NOTES A lawyer running a massive document production doesn't read every page anymore — she can't, and nobody expects her to. So when does that stop being…
- AI Tools for Practicing Lawyers
Episode 026 Volunteers and Hostages
SHOW NOTES Chad Van Horn built an AI petition review process that cut his firm's amendments by 80 percent. He also thinks AI is making lawyers dumber. Both are…
- AI Tools for Practicing Lawyers
Episode 025 Do Lawyers Need New Rules for AI? Judge Elizabeth Gunn Says ... Maybe Not
SHOW NOTES A federal bankruptcy judge just told us she doesn't personally use generative AI in her own chambers - and that's exactly why this conversation is…
- AI Tools for Practicing Lawyers
Field Note: Five Tips for Fighting Pro Se Litigants Who Use AI
SHOW NOTES An insurance company just spent $300,000 fighting a pro se litigant who had no lawyer — just ChatGPT. That number should worry every practicing…
- AI Tools for Practicing Lawyers
Episode 024 AI, Wellness and the 4th Bucket
Show Notes Lawyers wear exhaustion like a badge of honor — but what if the data on your wrist already knows you're running on empty? In this episode, Ron sits…
- AI Tools for Practicing Lawyers
Episode 023 Deepfakes and the Liar's Dividend
Has AI fundamentally changed the law of evidence, or has it just forced us to revisit principles that have always been there? That's the question at the center…
- AI Tools for Practicing Lawyers
Episode 022: The Jetsons Vacation In Florida
Show Notes How much work has to happen before AI can actually help a law firm? Everyone wants an AI-native practice, but almost nobody asks what has to be true…
- AI Tools for Practicing Lawyers
AI Builds: Gmail Digest
Most lawyers think about AI as a chat box. Ron argues that's already the old way of thinking — and the real leverage is in systems that run without you…
- AI Tools for Practicing Lawyers
Field Note: In Defense Of AI Notetakers
While AI note-takers grab the headlines, the real issue at stake in this episode is one lawyers have been dodging for decades: "Is AI notetaking actually…
- AI Tools for Practicing Lawyers
Episode 021 Law Firm AI: Custom Made Or Off The Shelf?
SHOW NOTES Most AI pitches to law firms start with a product. This one starts with an audit — and a question about whether buying software was ever the right…
- AI Tools for Practicing Lawyers
Episode 020: Pain Points, Grok And The Homeless Summer Associate
SHOW NOTES What if the smallest law firms are actually the best positioned to win the AI era? That's the provocation Ron opens with this week — and it comes…
- AI Tools for Practicing Lawyers
Episode 019 Bankruptcy Meets The AI Revolution
Show Notes Most bankruptcy lawyers still don't know what their own firm actually makes each month. Jenny Doling built a revenue dashboard in Claude to find out…
- AI Tools for Practicing Lawyers
Episode 018: Season 2, the $75 Consult and the Frankenstein Stack
Show Notes Episode 018 | Season 2 Premiere | Guest: Jennifer Grondahl Lee Season 1 taught you how to use AI. Season 2 is going to be harder. The question isn't…
- AI Tools for Practicing Lawyers
Episode 017 Training AI to Think Like Your Practice
Show Notes What are you actually doing with AI — and does it work? Ron and Heather put their tools down long enough to talk about what they've been building…
- AI Tools for Practicing Lawyers
Episode 016: Can an AI Judge Train You Better Than the Real One?
What if you could lose your case to an AI judge tonight, so you don't lose it to a real one tomorrow? For generations, lawyers learned advocacy the hard way…
- AI Tools for Practicing Lawyers
AI Builds: Ground Zero
Are "build an AI agent in 20 minutes" ads lying to you? Ron spent way more than 12 hours trying to find out. Ron set out to build the simplest possible AI…
- AI Tools for Practicing Lawyers
Field Note: Can Apple Intelligence Pass the File Cabinet Test?
SHOW NOTES NOTE: The File Cabinet Test is used to determine whether AI can discern the contents of every file in a connected drive. The star of Apple's WWDC…
- AI Tools for Practicing Lawyers
Episode 015: The Last Flintstones Lawyer
Most conversations about AI and legal writing focus on the tools. This one focuses on the lawyers. What does a Flintstones lawyer actually do on Monday morning…
- AI Tools for Practicing Lawyers
Field Note: Tiers Of The Clown
The question everyone is asking is wrong. When lawyers debate which AI tier is "smarter," they're arguing about a label — and labels end analysis. The better…
- AI Tools for Practicing Lawyers
Episode 014: Billable Hours and the AI Native Law Firm
SHOW NOTES Is the billable hour a liability you're voluntarily handing to your clients — and is AI finally giving lawyers a way out? Rich Rodgers has been…
- AI Tools for Practicing Lawyers
Workflow Options: Claude for Legal and Strongsuit
Workflow Options: From Prompts to Presets Every lawyer who has ever stared at a blank prompt box knows the feeling. AI promised to change how legal work gets…
- AI Tools for Practicing Lawyers
Episode 013 BigLaw, Privilege and an Unexpected "Wow!" Moment
When AI becomes a privilege problem, most lawyers are still treating it like a productivity hack. Solo and small firm attorneys hear constantly that AI saves…
- AI Tools for Practicing Lawyers
Field Note: I WannAI Hold Your Hand: Learning AI From AI
The AI training market for lawyers is broken. Not because there isn't enough of it — there's more than ever. The problem is almost all of it is aimed at the…
- AI Tools for Practicing Lawyers
Episode 012 – AI CLEs, Flintstones Lawyers & the Problem With Legal AI Training
I recently participated in a live AI panel at the Maryland Bankruptcy Bar Association Spring Break Weekend — one of the major annual CLE and networking events…
- AI Tools for Practicing Lawyers
Field Note: 21 Ways AI Can Hallucinate in Your Legal Brief
In this Field Note, Ron Drescher breaks down one of the most important—and misunderstood—risks in legal AI: hallucinations. The episode begins with the recent…
- AI Tools for Practicing Lawyers
Field Note: How BigLaw Associates Are Actually Using AI in Legal Drafting
This Field Note is a direct companion to the episode “21 Ways AI Can Hallucinate in Your Legal Brief.” If that episode showed how AI fails, this one shows how…
- AI Tools for Practicing Lawyers
Episode 011 From Dabbling to Deployment: How Lawyers Actually Use AI
There comes a moment for every lawyer using AI when experimentation turns into real-world application. That’s where the real opportunities begin. Ron and…
- AI Tools for Practicing Lawyers
Workflow Options: Foundation AI
Most legal AI conversations focus on drafting, research, discovery, and analysis. But what if some of the most valuable AI for law firms has nothing to do with…
- AI Tools for Practicing Lawyers
Episode 010 No Harvey FOMO: AI On A Budget
What’s the cheapest way for a lawyer to start using AI without creating expensive ethical, security, or sanctions problems? In Episode 010, Ron Drescher and…
- AI Tools for Practicing Lawyers
Field Note: Even Biglaw Gets The AI Hallucination Blues
Even elite firms can get burned by AI hallucinations. In this field note, Ron Drescher breaks down the recent Sullivan & Cromwell filing controversy, where an…
- AI Tools for Practicing Lawyers
Episode 009 Lawyer Moms (and Dads) and the 7-Minute AI Solution
In this episode, we’re joined by Carolyn Elefant, a longtime advocate for solo and small firm lawyers and the founder of MyShingle.com. We start with Carolyn’s…
- AI Tools for Practicing Lawyers
Workflow Options: Ivory Mind
In this kickoff “Workflow Options” episode, Ron Drescher takes a closer look at Ivory Mind, an AI document assistant designed to help professionals quickly…
- AI Tools for Practicing Lawyers
Episode 008 AI Discovery: A Safer, Defensible Way to Use AI in Discovery Work
AI can dramatically improve discovery work — summarizing productions, organizing documents, spotting patterns, building timelines, and making massive email…
- AI Tools for Practicing Lawyers
Field Note: Building the Stool — How to Implement the AI Discovery Standards
In this companion Field Note to Episode 008, Ron walks through the practical steps lawyers can take to implement the emerging AI discovery standards discussed…
- AI Tools for Practicing Lawyers
Episode 007: Folder Mania — When AI Comes to You
Every AI tool claims it can read your folders. We actually tested that claim — across ChatGPT, Claude, Gemini, and Microsoft Copilot — using a real-world…
- AI Tools for Practicing Lawyers
Field Notes: Confession of an AI Hallucinator
SHOW NOTES Confessions of an AI Hallucinator: Why Verification Isn’t Enough In this Field Note episode, Ron shares a candid story from his early use of ChatGPT…
- AI Tools for Practicing Lawyers
Episode 006 – 729 Hallucinated Cases Later… Lawyers Still Don’t Get AI
In this episode, Ron Drescher and Heather Gardner are joined by Professor Nancy Rapoport, co-author of A Short & Happy Guide to Artificial Intelligence and…
- AI Tools for Practicing Lawyers
Episode 005– How Lawyers Should Talk to AI
Using a simple framework to get better results from ChatGPT, Copilot, and other AI tools Lawyers already know how to structure thinking—we learned it for the…
- AI Tools for Practicing Lawyers
Episode 004 – AI In Tools You're Already Using
AI is everywhere right now — conferences, articles, LinkedIn posts — and many lawyers are getting tired of hearing about it. But what if the most useful AI…
- AI Tools for Practicing Lawyers
Episode 003 – AI Specialists: Where Do They Fit in Your Law Practice?
New AI tools for lawyers seem to appear every week — intake tools, research tools, document tools, and client communication tools. The pace can feel…
- AI Tools for Practicing Lawyers
Episode 002 - Primary Care AI Tools For Lawyers: ChatGPT, Gemini, Claude
A practical, non-hype discussion of ChatGPT, Gemini, and Claude for lawyers—how they’re similar, where they differ, and how to use them responsibly in real…
- AI Tools for Practicing Lawyers
Field Notes: Why Lawyers Should Stop Chasing AI Tools
In this episode, Ron Drescher discusses the overwhelming influx of AI tools available for lawyers and emphasizes the importance of integrating these tools into…
- AI Tools for Practicing Lawyers
Episode 001 – What Practicing Lawyers Need to Know About AI Right Now
Welcome to the inaugural episode of AI Tools for Practicing Lawyers. In this first episode, we explain what artificial intelligence actually means for lawyers…