AI Tools for Practicing Lawyers

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 — and then kept going, building analyzer skills for pay stubs, tax returns, bank statements, and Chapter 13 objections that her staff now runs without her. If a nationally recognized bankruptcy attorney and NACBA's incoming presid...

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 whether to adopt AI anymore — it's whether your firm's knowledge is organized enough for AI to actually use. When almost every hand in a room full of lawyers goes up to confirm they're using AI, the era of "should I...

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 with them. This isn't a roundup of tools you might try. It's an inside look at two practitioners who have spent serious hours creating AI-powered workflows for their own legal and legal-adjacent businesses — and what those proje...

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: draft the brief, argue the motion, get knocked down by the judge, learn why you were wrong. Litigation partner Chris Ryan built a different path. BenchSim AI lets lawyers upload their brief and opposing counsel's brief, then argue o...

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 legal workflow — a motion to extend time to file bankruptcy schedules — and discovered that "easy" and "AI-assisted" don't always mean the same thing. In this episode: Why Ron decided to test AI workflow-build...

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 2026? Apple Intelligence. Apple announced how Apple Intelligence is being incorporated into Siri. This prompts us to ask: Can Apple Intelligence finally make workflow automation accessible to ordinary lawyers? In this episode: Why Apple&a...

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 after they've finally decided to move? What does a Simpsons lawyer do when they discover their favorite tool isn't safe for client data? And what happens when the question isn't whether to adopt AI — but whether you'll s...

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 question isn't which tier is best . It's what capabilities am I actually buying , and whether those capabilities match the task in front of you. Ron's File Cabinet Test experiments proved this the hard way: Enter...

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 building AI-native legal tools since before most lawyers knew what a large language model was. He's a practicing startup attorney, a four-time founder, and the creator of Start Legal — an AI platform designed to give founders a runnin...

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...