AI in Midsize Law Firms: Client Pressure, Privilege Risk, and What Actually Works

Three first-time guests join me to talk about AI showing up in mid-size to small law practices, whether lawyers are ready for it or not. Russell Taber, Greg Teufel, and Tom Thompson dig into the disruption that occurs when clients bring AI-drafted work to their lawyers to help with the case, the unsettled question this creates with privilege waiver, and whether firm size changes how a practice adopts new technology. Buster the dog makes an appearance too, because staying human matters. Guest Introduction Russell Taber is a litigation partner at Riley and Jacobson in Nashville. Greg Teufel is the founding partner of OGC Law in Pittsburgh. Tom Thompson practices with Blaney and Thompson in Chicago and serves as CEO of Test My Witness. Key Takeaways Clients are showing up with AI already in the mix, whether their lawyers want that or not. Greg sees it on the transactional side with contract review tools and on the litigation side with drafted complaints, and both he and Tom described spending real time explaining why the output wasn't usable. The privilege question around AI use is still unsettled. Russell pointed to the Hepner case out of the Southern District of New York, where a judge found that AI use waived work product protection, and noted that more recent cases have gone the other way. Nobody on the panel had a clean answer for this yet. Firm size changes the calculus on tool adoption. Bigger firms can spread the cost of an AI platform across enough clients to justify it. Smaller firms need tools priced and scoped for a single use case, and every guest agreed that a platform trying to do everything for everybody usually ends up too expensive and too broad to be worth it. Keyword search is still doing most of the heavy lifting in eDiscovery. I asked directly whether people were still relying on keywords over predictive coding or newer tools, and the answer from all three guests was yes, even now. The biggest wins mentioned by the panel were narrow and practical. Greg pointed to AI-powered search. Russell mentioned using AI to listen to oral argument outlines while running. Tom talked about Test My Witness improving how his clients perform under cross-examination, based on results he's seen firsthand over the past year and a half. Chapter Markers 00:00:00 Introduction and guest panel: Russell Taber, Greg Tufo, and Tom Thompson 00:04:00 Are clients bringing AI-generated work into their cases 00:07:14 Why clients trust AI the same way they trust WebMD 00:11:17 Engagement letters, cost warnings, and privilege waiver risk 00:12:42 The Hepner case and whether AI use waives work product 00:14:09 Does firm size change how law firms adopt technology 00:15:36 AI tools at a five-attorney firm versus a larger one 00:17:31 The risk of investing in AI tools that disappear in a year 00:18:46 Carl on the early struggles of training AI into Test My Witness 00:20:57 Why younger lawyers are sometimes the most resistant to AI 00:22:49 Keyword search versus predictive coding, still going strong 00:27:10 What vendors could do to earn more trust from smaller firms 00:28:49 The case for free trials on real cases instead of demo data 00:30:57 Startup funding pressure and what it does to pricing 00:33:11 Final round: the AI tool that has helped each guest the most 00:36:06 An idea for using emotional AI to connect with prospects 00:38:37 Buster the dog and closing remarks Keywords AI in law firms, generative AI legal, midsize law firm technology, eDiscovery, legal AI adoption, AI hallucinations, work product privilege, predictive coding, keyword search eDiscovery, AI contract review, legal tech pricing, small firm AI tools, Test My Witness, witness preparation, AI-powered legal research, litigation technology, client AI use, legal AI ethics, ESI Bytes podcast, Russell Taber, Greg Tufo, Tom Thompson