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 a specific
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June 2026 Issue of Personal Strategy Compass Newsletter is Out
The Halftime Locker Room and the Fallacy of Blind Discipline
With the 2026 World Cup underway, it is easy to get caught up in the drama of the opening whistle. But any coach will tell you that games are rarely won in the first few minutes. They are won or lost in the locker room
New Podcast Episode: The Expanding Minefield of Legal AI
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 strictly
The Hidden Instruction Problem for Agentic AI and All Other AI
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 May Issue of Personal Strategy Compass Is Out
The May issue of Personal Strategy Compass newsletter is live, picking up in the silence left behind after April’s “acoustic stage” was cleared of its noise and inherited obligations.
If April was about the courage to strip the stage down to its essential signal, May is about the craft required to sustain it.
The image
The Competence Trap: Anatomy of a Captured Claude #Fail
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 April Issue of Personal Strategy Compass Is Out
The April issue of Personal Strategy Compass is out, and this one took longer to find its frame than most.
The image that finally unlocked it was Bruce Springsteen’s Tunnel of Love tour. Not the Born in the USA stadium spectacle that preceded it. The moment after, when he stripped the stage down to almost
Liner Notes for My Low Album
When I started posting about AI this year, I did not realize that I was beginning my own version of David Bowie’s Low album.
I use that comparison carefully. Low matters here not as a code book or a track-by-track template, but as an allusion to emergence, fracture, atmosphere, and a break in method that
Standing Waves
There are moments in a long AI session when the exchange stops feeling linear.You are no longer simply asking a question and receiving an answer. You are no longer even refining a prompt in the ordinary sense. Something else begins to happen. Certain phrases return with altered weight. Certain errors recur, but not identically. Certain
AI as the Unreliable Witness and the Appearance of Completion
Coherence degrades while fluency improves.
The central problem is not that AI systems sometimes fail. Of course they fail. Nor is the main problem that they occasionally hallucinate, wander, or produce obvious nonsense. Those are manageable problems because they announce themselves early. The more interesting and professionally dangerous problem is that a system can become
The Threshold Moment
At a certain point in a long AI session, I can feel the texture change.The words are still smooth. The tone is still confident. But something underneath has started to slide and give way. The session is still moving forward, yet the logic is no longer holding together in the same way.That happened to me
Fresh Voices at Three: What Listening Taught Us About AI, LegalTech, and the Next Generation
When Tom and I started the Fresh Voices series on The Kennedy-Mighell Report podcast, we had a pretty simple idea.A lot of the most interesting work in legal tech seemed to be coming from people who were newer to the field, earlier in their careers, or just not as widely known yet as they
What Scarcity Taught Computing, and AI Might Need to Relearn
“A larger context window can create the feeling that a cognitive problem has been solved, when sometimes all that has happened is that disorder has become harder to notice.”
I was in Silicon Valley recently for the initial meeting of the University of Michigan Law School AI Advisory Council. With a little free time around
The Helpfulness Trap: Anatomy of an AI Recursive Failure Loop
“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 recursive failure loop
The Intelligence Bureaucracy
Why the OpenAI Hiring Surge Signals a Crisis of Professional Control
The management problem in AI is no longer whether the models are improving. They are. The management problem is whether the working surface is becoming more dependable or less.That is why the recent OpenAI hiring story on its plan to nearly double its workforce
The Protocol Layer: Democratizing AI Rigor for Everyone
Intelligence is Raw Material. Protocol is the Product.
We often confuse the power of a new tool with the effectiveness of its application.The giants of the AI industry have provided us with a magnificent “Power Grid.” They have given us raw, unmanaged intelligence at a scale previously unimagined. But we must be clear-eyed about one