In the latest episode of The Kennedy-Mighell Report, Tom Mighell and I turned the spotlight inward to talk about the course I just finished teaching at the University of Michigan Law School called Legal Technology Literacy and Leadership. This course is considered a practical simulation class. It was built this past semester around
legalai
New Podcast Episode: The Expanding Minefield of Legal AI
By Dennis Kennedy on
The Expanding Minefield of Legal AI
I’ve been tracking a subtle but dangerous shift in the legal tech landscape. For the last few years, the entire industry has been obsessed with “hallucinations”—obvious, glaring errors like fake case citations. But as Tom Mighell and I discussed on episode 418 of The Kennedy-Mighell Report, focusing…
The Hidden Instruction Problem for Agentic AI and All Other AI
By Dennis Kennedy on
The Door in the Hallway: Agentic AI and the Illusion of Control
We used to talk a lot about the concept of a customized, bounded news feed designed to give professionals exactly what they need to know, and nothing they don’t. It was usually called the “Daily Me.”
Lately, I’ve been trying to build a…
The Competence Trap: Anatomy of a Captured Claude #Fail
By Dennis Kennedy on
The prevailing narrative I hear in the legal world is that Claude is the “most human” of the LLMs and, especially, a nuanced, sophisticated writer. When I report that the system has begun to fail my specific research protocols, the common response is a suggestion that I am simply using the wrong version and a…
The Helpfulness Trap: Anatomy of an AI Recursive Failure Loop
By Dennis Kennedy on
“Polishing the Mirror While the House Burns: Why Your AI is a Liability”
The Editor’s Introduction: A Note on the “Sliver of Silence”
You’ll be looking below at a self-autopsy performed by an AI on its own failure.
What follows is the raw, unwashed output of an LLM that found itself in an AI recursi…
Building the Stochastic Sandpit for AI
By Dennis Kennedy on
We’ve spent the last couple of years treating generative AI like a vending machine. Select a task. Insert a prompt. Retrieve a product. And to be fair, in many legal and professional contexts that’s exactly the right frame: accuracy and precision matter and “creative” output in payroll or billing codes is usually just a polished…
The End of the Magic Wand: Why 2026 Demands Resilience Prompting
By Dennis Kennedy on
For more than two years, lawyers have been told that success with generative AI depended on writing better prompts and a search for the perfect “magic wand” prompting formula. That was the wrong lesson. The real change in 2026 is not found in the model itself, but in the professional posture required to use it.
Prompting or Negotiating? A Systems Design Lesson for Legal AI
By Dennis Kennedy on
I had a long session recently with a public genAI tool that taught me something more important than the topic I started with.
The lesson was not about whether the model was “smart enough.” It was about control. At a certain point, I realized I was no longer simply prompting an LLM. I was negotiating…