Episode 034 Jane Jetson’s Book Club and the Demise of Prompting
Everyone says AI needs a human in the loop, but nobody explains why human judgment is actually better than a machine trained on more data than any lawyer will ever see. Maura Grossman, the researcher who proved machine learning could beat lawyers at document review, explains why culture, morals, and wisdom stay human, why harsh sanctions haven't stopped hallucinations, and why generative AI's hyped advantage in e-discovery disappears under a fair test. Then Heather declares prompting dead, and Ron and Maura push back.
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Show Notes
Students in 2026 can't imagine writing a ten-page paper without ChatGPT. Judges are split between refusing to touch AI and quietly using it to draft. Lawyers keep filing hallucinated citations despite years of headlines and sanctions. Maura Grossman, the lawyer and computer scientist who helped prove machine learning could outperform human document review, joins Ron and Heather to separate what AI does well from what has to stay human. Is human judgment actually wiser than AI judgment, or is it just a bigger pile of data?
In this episode:
- The state of the bench in October 2026: a "wild west" of judges who refuse AI, judges who use it freely, and almost no uniform guidance
- Why judicial resistance to AI is mostly fear, and how an hour of hands-on training changes it
- Heather's challenge: lawyers miscited cases for generations, so shouldn't the standard focus on the final work product rather than how it was produced?
- Whether pro se litigants deserve more slack than licensed attorneys for hallucinated citations
- Why harsh sanctions haven't reduced hallucinations, and a judge who solved one with a simple warning
- The "sandwich approach": the judge thinks first, AI helps in the middle, the judge decides at the end
- The live debate over whether prompting is dead, and why "just talking to your AI" is still prompting
- Maura and Gordon Cormack's research showing generative AI's claimed edge over older machine learning in e-discovery largely disappears in an apples-to-apples comparison
- Why human judgment matters: alignment, culture, morals, and Bostrom's paperclip problem
- What happens to mentorship and learning when AI does the research a junior lawyer used to do
We also discuss:
- A law student who admitted he never read a single case in three years, summarizing everything through ChatGPT
- Maura's classroom fix: a personal journal where AI use is prohibited
- Clients who arrive convinced by ChatGPT that their case is worth a million dollars
- The lawsuit alleging ChatGPT told a litigant she was being snowed by her lawyer
- Whether AI companies should compensate authors and artists whose work trained their models
- Practice Signals: a new solo litigator who wants to add contract drafting with zero transactional experience
Key Takeaway
Maura's closing advice cuts through most of the noise: the problem should drive the solution. Don't buy AI because the firm down the street has it. Find the pain point in your own practice, then find the tool that fixes it. And whatever tool you pick, it can't do the thinking a judge or lawyer is paid to do. That stays with you, at the start and at the end.
This season the show shifted from Flintstones, Simpsons, and Jetsons to users and builders, and this episode lands on both. Users need to know enough to verify what the tool hands them. Builders need to remember that a beautifully engineered workflow doesn't make them competent in an area of law they've never practiced. Jane Jetson may think prompts are so March 2026. Maura's research says the jury is still out.
Mentioned in This Episode
- Maura R. Grossman, Research Professor, School of Computer Science, University of Waterloo; Adjunct Professor, Osgoode Hall Law School; Visiting Professor, Duke Law School
- The Judicious Judge's Guide to Generative Artificial Intelligence and Large Language Models (forthcoming)
- "Utopia or Dystopia" paper on self-represented litigants and AI
- Grossman and Grimm general-principles paper, Sedona Conference Journal (2025)
- Grossman and Cormack, 2011 study on technology-assisted review in e-discovery
- Judge Paul Grimm (Podcast Episode 023 Deepfakes and the Liar's Dividend)
- Gordon Cormack, University of Waterloo
- Judges Maritza Braswell (Colorado), Scott Schlegel (Louisiana), and Xavier Rodriguez (Texas) and their judges-only AI group
- Federal Judicial Center AI toolkit for federal judges
- National Center for State Courts and Thomson Reuters Institute
- Georgia Bench and Bar Conference
- MIT research on brain engagement when writing with LLMs
- Nick Bostrom's paperclip maximizer thought experiment
- Federal Rule of Civil Procedure 11
- Nippon Life lawsuit against OpenAI
- ChatGPT, Claude, Gemini, Vertex AI, Google Cloud, Microsoft
- Harvey, Legora
- Westlaw, Lexis
- Reddit
