330: Why Claude Gets Dumber—and How Lawyers Can Use AI Better

In this episode, Ernie Svenson talks with Docket Drafter co-founder Tommy Eberle about what lawyers need to understand to use AI tools like Claude more effectively. They unpack why Word documents consume so many tokens, why AI performance can decline during long chats, how context windows and compaction affect results, and when to use different Claude models and thinking levels.

Tommy also explains how lawyers can use AI to organize files, automate repetitive document work, and build more efficient workflows—without needing to become programmers themselves.

Chapters

0:05 Why AI Frustrations Make Sense
3:03 From Coding To Legal AI
8:05 Making Word Agent-Friendly
16:20 Why Claude Gets Dumber
26:21 Models, Thinking, And Compaction
34:33 Files, Folders, And Better Prompting

Show Notes

The 80/20 Principle (my techlaw newsletter)
The Inner Circle (my online community for lawyers)
Tommy Eberle's LinkedIn page
Tommy's Email Address: tommy@docketdrafter.com
Docket Drafter
https://www.youtube.com/@DocketDrafter

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