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

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

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Jaksot(333)

333: Why AI feels more like email than the web

333: Why AI feels more like email than the web

In this episode, Ernie Svenson talks with Greg Siskind, who has practiced immigration law for 35 years and wrote a book about marketing on the internet back in 1996, when that was a peculiar thing for...

29 Syys 46min

332: The role your firm needs but can't name

332: The role your firm needs but can't name

A few weeks ago, one of Sarah Persich's clients dropped an AI agent into their Slack workspace. Sarah gave it the criteria her client's intake team is supposed to follow on calls — build rapport, hand...

15 Syys 37min

331: When AI Starts to Look Like Judgment (with Carolyn Elefant)

331: When AI Starts to Look Like Judgment (with Carolyn Elefant)

Carolyn Elefant has been practicing law for thirty-five years and writing about solo practice for almost as long. In this episode she and Ernie get into how AI is changing litigation — not in theory, ...

1 Syys 38min

329: Introduction to Claude and Its Potential

329: Introduction to Claude and Its Potential

Most lawyers using Claude are only scratching the surface of what it can do. In this episode, Ernie Svenson talks with former litigator and software founder Nick Chapleau about using Claude as more th...

21 Heinä 38min

328: The Golf Lesson That Changed How I Teach AI

328: The Golf Lesson That Changed How I Teach AI

Most AI training for lawyers is shiny-object stuff — nine prompts, the "ultimate playbook" — and that's exactly why none of it sticks. My old golf instructor figured this out decades ago, and he taugh...

23 Kesä 10min

327: How a Seasoned Litigator Became an AI Power User

327: How a Seasoned Litigator Became an AI Power User

*]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20s...

26 Touko 38min

326: Perplexity for Lawyers: AI Research With Sources

326: Perplexity for Lawyers: AI Research With Sources

In this episode, we cover Perplexity—what it is, how it works, and why it deserves attention from solo and small firm lawyers. Ernie explains how Perplexity differs from traditional Google research by...

12 Touko 8min

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