Why “Good Enough” AI Fails in Law and How the Last Mile Is Where Real Value Gets Created

Dec 19, 2025

What happens when AI gets powerful, but verification becomes the bottleneck? In this candid, end-of-year conversation, Clearbrief Founder & CEO Jacqueline Schafer breaks down why accuracy, sourcing, and trust - not raw model power are the real constraints on legal AI adoption today. Listeners walk away with a clear mental model for where AI actually delivers ROI in law firms and corporate legal teams, and why the “last mile” is the battleground that matters now. 

Hosted by David Cowen

Key Topics Covered:

• Why AI output that can’t be verified fast is worse than useless, and how verification time kills ROI
• The “last mile” framework: where legal workflows break down and why most tools stop too early
• How Clearbrief was built around mistake-catching before GenAI and why that design choice aged perfectly
• What customer discovery really looks like (200+ lawyer interviews, brutal feedback included)
• The shift toward insourcing: which litigation and investigation tasks stay in-house and which never will
• Why general-purpose chatbots help with drafting, but fail at delivery, defensibility, and trust
• A practical metaphor for AI adoption speed: the engine is fast, the road isn’t, and lawyers are the drivers

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💡To learn more about the future of legal innovation, visit https://cowengroup.com/

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