AI Tools for Practicing Lawyers

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 done — but a single chatbox isn't a workflow. The legal AI world is splitting in two: enterprise ecosystems building choreographed plugin infrastructure, and vertical tools purpose-built for specific practice areas. The real question isn...

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 time. What they hear far less often is that the AI tool they chose — and more specifically, the tier they're using — may have just waived their client's privilege. This episode forces that conversation. If you're putting client...

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 wrong lawyer. LinkedIn is full of Jetsons lawyers talking to other Jetsons lawyers, while the majority of practitioners are still trying to figure out how to create a PDF. So if the training doesn't meet you where you are, what...

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 for Maryland bankruptcy lawyers. The panel featured retired federal judge Paul Grimm as moderator, along with Patti Jefferson, Nancy Rapoport, and Ron Drescher. But this episode is not simply a replay or recap of the panel. Instead, we use t...

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 Sullivan & Cromwell filing admitting AI-generated errors, with a close look at the now-famous Schedule A . While most commentary has focused on fake citations and misquotes, Ron highlights the more subtle—and more dangerous—types of hall...

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 lawyers are adapting anyway. Drawing from a real-world Reddit thread with dozens of BigLaw associates, this episode breaks down the actual workflows lawyers are using today —not theory, not vendor demos, and not CLE talking points. What emer...

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 Heather talk to Colorado bankruptcy attorney Matt McCune , a 25-year practitioner who isn’t just talking about AI—he’s rebuilding his law practice around it. Matt shares how AI is transforming the entire structure of a law firm and why the lawyer...

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 writing? In this Workflow Options minisode, Ron Drescher explores Foundation AI, a company focused on one of the oldest and most frustrating business problems in history: incoming document chaos . Ron revisits his Four Buckets of a Law Firm...

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 Heather Gardner tackle one of the most common questions lawyers are asking right now: I’m ready to try AI, but I don’t want to pay an arm and a leg—and I don’t want to get into trouble. The conversation starts with the premium end of the mark...

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 emergency brief reportedly contained multiple citation and quotation errors that opposing counsel exposed first. The lesson is not that one firm slipped—it’s that polished AI output can create false confidence in any lawyer, especially w...

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 upcoming AI for Lawyer Moms workshop —why she created it, who it’s for, and how AI is uniquely positioned to help lawyers working in the “crevices” of their day. From there, we shift into a timely discussion of Management Service Organiza...

In this kickoff “Workflow Options” episode, Ron Drescher takes a closer look at Ivory Mind, an AI document assistant designed to help professionals quickly understand and organize their materials. At first glance, Ivory Mind didn’t seem to fit the frameworks Ron has been developing on the show—like the Three-Legged Stool and Folder Mania tests. But after a deeper look, a different question emerged...

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 in Jeffries v. Harsco . He breaks the process into a simple three-legged stool : choosing the right vendor , properly configuring the tool , and handling the lawyer-side workflow and documentation needed to make AI use in discovery more defe...

AI can dramatically improve discovery work — summarizing productions, organizing documents, spotting patterns, building timelines, and making massive email chains usable. But most lawyers still lack a clear, defensible framework for using AI on discovery materials. In this episode, Ron and Heather break down a recent Kansas federal court opinion and explain why it may become one of the most import...

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 48-document Chapter 13 case file. The results were all over the place. Ron introduces the "File Cabinet Test": a threshold check that tells you whether an AI tool is actually seeing what you're giving it, before you trust it with a...

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 — including the moment he nearly relied on hallucinated legal citations in a client memo. This is not just a confession. It’s a practical warning for lawyers tempted to use consumer AI tools for legal research, drafting, and filings without...

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 Legal Ethics , to explore how lawyers can use AI responsibly — and why so many are getting into trouble doing it wrong. From hallucinated cases to ethical missteps, the conversation dives into the growing “trust gap” between large firms wit...

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 bar exam with IRAC. But when it comes to AI, most of us were never given a framework for how to communicate with it. In this episode, we introduce RTCF (Role, Task, Context, Format) —a simple, flexible structure that helps lawyers get better,...

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 tools aren’t new platforms you need to learn at all? In this episode of AI Tools for Practicing Lawyers , Ron Drescher and Heather Gardner talk about how AI is already built into the tools lawyers use every day — from email and Zoom to Google W...

New AI tools for lawyers seem to appear every week — intake tools, research tools, document tools, and client communication tools. The pace can feel overwhelming. In this episode, Ron and Heather step back from the “latest tool” conversation and ask a more useful question: Where do AI tools fit inside a law firm’s systems? Instead of cataloging products, Ron introduces a simple framework for evalu...

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 legal workflows. In this episode, Ron and Heather take a 30,000-foot view of the “Big Three” AI tools for lawyers: ChatGPT, Gemini, and Claude. Are they really different? Does it matter which one you use? And how do you avoid the well-publicize...

In this episode, Ron Drescher discusses the overwhelming influx of AI tools available for lawyers and emphasizes the importance of integrating these tools into existing systems rather than getting lost in the multitude of options. He categorizes lawyers into three levels of engagement with AI—Flintstones, Simpsons, and Jetsons—and provides tailored advice for each group on how to approach the delu...

Welcome to the inaugural episode of AI Tools for Practicing Lawyers . In this first episode, we explain what artificial intelligence actually means for lawyers today — separating practical tools from hype, speculation, and fear. This podcast is designed for practicing attorneys who want clear, real-world guidance on how AI can be used responsibly and effectively in a law practice right now — witho...