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, but in the cases she's handling right now.

Carolyn walks through experiments she's run and posted publicly, including having AI draft the judge's opinion from both briefs before she wrote her reply, and hiding instructions inside a brief to see which AI tools would follow them. One tool refused. One followed them. The third declined the part it considered unethical and went along with the part it considered harmless — which is the interesting one, because it looks a lot like judgment.

They also cover which tools she reaches for and when, why she pays for the business version instead of the free one, where a lawyer should start if all of this feels overwhelming, and her upcoming 'Bellwether AI Litigator' conference on September 17 and 18.

Chapters
0:05 Episode Overview
1:45 Smith.ai Sponsor
2:30 A Small Firm That Fights Big Energy
7:09 Her First AI Experiments
10:46 Making AI Write the Judge's Opinion
12:59 The Prompt Injection Test
14:44 When AI Starts to Look Like Judgment
17:38 Connecting Claude to Email, Files, and Court Listener
25:02 Where a Lawyer Should Start
27:02 Free vs. Paid, and What Happens in Discovery
28:35 The Bellwether Litigator Conference

Resource Links

• The Bellweather AI Litigator Conference info
• Early Bird Registration (special price)
• Carolyn's LinkedIn profile (follow her from here)
• The 80/20 Principle (my techlaw newsletter)
• The Inner Circle (my online community for lawyers)

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