Episode 012 – AI CLEs, Flintstones Lawyers & the Problem With Legal AI Training
Ron Drescher, Heather Gardner, and Kathryn Boling reflect on a live AI CLE panel presented at the 2026 Maryland Bankruptcy Bar Association Spring Break Weekend. The discussion explores why legal AI education remains so difficult, how Flintstones, Simpsons, and Jetsons lawyers experience AI differently, and what law firms should actually focus on before adopting new AI tools.
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Show Notes
I recently participated in a live AI panel at the Maryland Bankruptcy Bar Association Spring Break Weekend — one of the major annual CLE and networking events for Maryland bankruptcy lawyers.
The panel featured retired federal judge Paul Grimm as moderator, along with Patti Jefferson, Nancy Rapoport, and Ron Drescher. But this episode is not simply a replay or recap of the panel.
Instead, we use the experience to explore a much bigger question:
Is the legal profession actually teaching AI effectively?
In this episode:
Why AI CLE panels may struggle to teach lawyers at vastly different technology levels
The continuing evolution of the Flintstones / Simpsons / Jetsons framework
Why some lawyers may never need to become “Jetsons-level” AI users
Patti Jefferson’s live AI demonstration using the Red Lobster bankruptcy confirmation order
The rise of agents and workflow automation beyond traditional prompting
Nancy Rapoport’s warnings about hallucinations, supervision, and professional responsibility
Why “hallucination verification” may erase much of AI’s promised time savings
A comparison between AI hallucinations in law versus medicine
Why many firms remain stuck at “sub-Flintstones” technology levels
How to identify the pain points inside your law firm before adopting AI
Why your firm should conduct a “Tech Stack Audit”
We also discuss:
Dropbox and document organization for high-volume bankruptcy practices
The growing divide between consumer AI and enterprise AI
Why “ChatGPT” is no longer a meaningful description without understanding the underlying plan and governance structure
The importance of the “Three-Legged Stool” for safe legal AI deployment:
Vendor protections
Proper configuration
Human supervision
Download: Tech Stack Audit Spreadsheet
This episode includes a downloadable spreadsheet template designed to help lawyers:
identify all software subscriptions,
calculate monthly and annual costs,
evaluate what they are actually getting from their tech stack,
and determine where they fall on the Flintstones / Simpsons / Jetsons spectrum.
If you complete the spreadsheet and would like us to discuss it anonymously (or publicly) on a future episode, send it to:
We’d love to see how lawyers are actually building — or struggling to build — their AI and technology infrastructure.
Mentioned in This Episode
ChatGPT
Claude
Gemini
Harvey
IvoryMind
Google Workspace
Dropbox
Clio
Foundation AI
Key Takeaway
Most legal AI education still treats lawyers as if they are all at the same level of technological fluency.
But Flintstones lawyers, Simpsons lawyers, and Jetsons lawyers may not even be attending the same CLE — even if they are sitting in the same ballroom.
