Why AI Won't Fix Your Broken Workflow with John Grant

The Client Side of Legal AI with Hilary Bowman

Hilary Bowman built Querious to solve the most frustrating moment in legal practice - when something unexpected comes up in a client meeting and the lawyer has to say "let me research and follow up." After more than a decade as a healthcare attorney at law firms and in-house at enterprises like IBM, she founded Querious to sit inside attorney-client conversations on Zoom, Teams, or phone and surface issues, questions, and follow-ups in real time. In this conversation, she flips the usual AI for lawyers script and asks what these tools actually do for clients - why most clients want a relationship partner instead of a black box, why timely follow-ups beat fancy portals, and how language tools finally let lawyers meet clients where they are. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/hilarybowman/ [https://www.linkedin.com/in/hilarybowman/] https://www.querious.ai/ [https://www.querious.ai/] 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free:  [https://www.spellbook.legal/newsletter]https://www.spellbook.legal/newsletter [https://www.spellbook.legal/newsletter] 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free:  [https://www.spellbook.legal]https://www.spellbook.legal [https://www.spellbook.legal] 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:50 - Meet Hilary 2:03 - What Querious does in a client meeting 2:45 - From healthcare law to founding a startup 4:10 - What clients actually want from a lawyer 5:21 - The lawyer as relationship partner and traffic cop 6:55 - The black box problem of hourly billing 7:30 - Bridging asymmetries between lawyer and client 8:03 - Why law can't have a Domino's Pizza tracker 10:36 - The most powerful LLM unlock for clients 12:38 - Where AI ends and creative lawyering begins 14:22 - Change costs and tool adoption 15:55 - Speed to value: narrowing the scope 17:45 - Building feedback loops with clients 20:18 - One thing to implement on Monday 22:15 - Connect with Hilary

Why AI Won't Fix Your Broken Workflow with John Grant

AI tools won't solve your overwhelm if your processes are the problem. John Grant is a fourth-generation lawyer turned workflow consultant. He spent a decade in tech before practicing law, and another eleven years helping firms fix how work actually moves. In this conversation, he breaks down the "magical thinking" behind AI adoption, why the real bottleneck is almost never where lawyers think it is, and how speeding up the wrong step actually makes everything worse. He also explains the concepts of "definition of done" and "definition of ready," why legal has an immature relationship with quality assurance, and what courts are already seeing as AI-assisted filings flood systems that aren't built to handle them. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/johnegrant/ [https://www.linkedin.com/in/johnegrant/] https://agileattorney.com [https://agileattorney.com]  [https://greenlinelegal.com]https://greenlinelegal.com [https://greenlinelegal.com] 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free:  [https://www.spellbook.legal/newsletter]https://www.spellbook.legal/newsletter [https://www.spellbook.legal/newsletter] 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free:  [https://www.spellbook.legal]https://www.spellbook.legal [https://www.spellbook.legal] 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:42 - Meet John Grant 2:13 - What is Greenline? 3:18 - AI hasn't reduced work 4:30 - The optimism bias and the planning fallacy 6:00 - AI and the last mile problem 7:09 - Output vs. productivity: the developer study 8:06 - Effort is not value 9:21 - Reimagining what value actually means 10:00 - There's only one bottleneck 11:16 - Why improving the wrong step makes things worse 12:10 - AI-assisted pro se filings are flooding courts 13:45 - More but worse vs. less but better 14:00 - Where bottlenecks actually form in legal 15:27 - Legal's immature relationship with quality assurance 16:15 - Quality control is chosen friction 17:21 - Definition of done and definition of ready 18:06 - Failure demand and rework 19:29 - Lawyering is a caregiving profession 22:39 - The board game analogy: multiple ways to lose 23:32 - The Agile Attorney 101 podcast series 25:04 - Takeaway: AI won't solve overwhelm without design 25:38 - Connect with John

Are AI Notetakers Ethical for Lawyers? with Wendy Meadows & Michael Eisenberg

In this episode, Mike walks through the New York City Bar's recent opinion on using AI to record, transcribe, and summarize client conversations, and boils it down to four duties you probably already follow. Then mediator Wendy Meadows shares her full workflow, including Fathom for capture, Clio for document production, Spellbook for quality control, and how it turned a two-hour MOU into a 20-minute job. Michael Eisenberg breaks down consent rules, one-party vs. two-party states, and why none of this is actually new. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter [https://www.spellbook.legal/newsletter] 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal [https://www.spellbook.legal] https://www.linkedin.com/company/spellbookai/posts/?feedView=all [https://www.linkedin.com/company/spellbookai/posts/?feedView=all] https://www.linkedin.com/in/mikewhelanjr/ [https://www.linkedin.com/in/mikewhelanjr/] https://www.linkedin.com/in/scottas/ [https://www.linkedin.com/in/scottas/] 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:46 - The New York City Bar opinion (Formal Opinion 20256) 2:45 - Risk 1: Consent and one-party vs. two-party states 4:48 - Risk 2: Confidentiality and ABA Rule 1.6(c) 6:06 - Risk 3: What if the client records the call? 8:46 - Why these rules aren't new 9:05 - Wendy's practice: mediator on Zoom all day 10:00 - Turn off the defaults 10:51 - Using it like an associate 12:27 - Drafting direct examination from a transcript 13:08 - Spellbook as the quality control layer 14:48 - Predicting the future: insights in context 16:01 - Why the good outweighs the bad 16:37 - Connect with Wendy and Michael

How a Business Lawyer Reviews a 56-Page Contract with AI with Chris Brown

Contract review is tedious, but missing something can be expensive. In this episode, Chris Brown of Pixel Law shares his screen as he reviews a 56-page Asset Purchase Agreement using Spellbook. See how effective AI tools can help you: - Surface unknown risks, - Draft clauses like indemnification and delivery terms, and - Update you on substantive legal issues within a contract. Chris also shares how he uses Spellbook for a "second opinion," and why he believes AI will change the practice of law. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/thepixellawyer/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:37 - What contract review looked like before AI 1:52 - The document: a 56-page asset purchase agreement 2:11 - High-level risk overview 4:18 - Diving into indemnification 8:25 - Non-compete analysis and Florida law 10:46 - Breaking down the purchase price 15:08 - Reps and warranties review (35 issues in 9 pages) 17:52 - Running the same prompt twice for a second opinion 18:24 - Closing deliveries and what's missing 22:08 - Catching missing terms across the document 24:44 - Compare to Market feature 28:35 - What stood out most from the process 29:51 - When to trust AI vs. your own judgment 31:00 - How to get started with AI tools 32:09 - Wrap up

Is Your Client's AI Chat Discoverable? with Leslie Bender & Craig Linton

What happens if your client asks ChatGPT for advice about their case? Is that discoverable? Is it your fault if you didn't warn them it might be? Leslie Bender and Craig Linton join the show to unpack two cases: Heppner and Warner v Gilbarco, that seem to reach opposite conclusions as judges try to draw lines around privilege, work product, and AI in an area where the rules haven't caught up to the tools. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲: Spotify: https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq [https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq] Apple: https://podcasts.apple.com/us/podcast/ai-in-practice/id1846506529 [https://podcasts.apple.com/us/podcast/ai-in-practice/id1846506529] 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁𝘀: https://www.linkedin.com/in/lescbender/ [https://www.linkedin.com/in/lescbender/] https://www.linkedin.com/in/craigalinton/ [https://www.linkedin.com/in/craigalinton/] 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter [https://www.spellbook.legal/newsletter] 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal [https://www.spellbook.legal] https://www.linkedin.com/company/spellbookai/posts/?feedView=all [https://www.linkedin.com/company/spellbookai/posts/?feedView=all] https://www.linkedin.com/in/mikewhelanjr/ [https://www.linkedin.com/in/mikewhelanjr/] https://www.linkedin.com/in/scottas/ [https://www.linkedin.com/in/scottas/] 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:49 - Meet Leslie Bender 2:31 - Meet Craig Linton 3:31 - Attorney-client privilege and work product 101 5:54 - Clients have always gone rogue with case info 8:00 - The Heppner case: a CEO, AI, and a 31-point memo 11:21 - Does it matter if the lawyer directed it? 13:00 - Warner v Gilbarco: the pro se counterpoint 16:08 - What discoverability means for pro se litigants 19:21 - Assume your AI self-help is discoverable 21:37 - The engagement letter hack 23:19 - Should we encourage or discourage client AI use? 25:06 - Lawyers as AI consumers: is Claude enough? 28:10 - Reasonable privacy expectations vs. the fine print 30:49 - Three predictions for the next 10 years 33:06 - Connect with Leslie and Craig