AI Tools for Practicing Lawyers · 2026-04-01 · 37 min
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 anything that matters. Because if the AI is faking it - cherry-picking by relevance, wandering outside your folder, or missing documents entirely - that's not an AI intelligence problem. That's a visibility problem. And for lawyers, visibility is everything. This episode is a deep dive into folder access, document security, workflow design, and what it really means to close the trust gap in your practice.
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