It started with a routine task, as it usually does. I was using Claude to review a draft critique of an article I had some doubts about, checking the research behind a few of its assertions and testing its logic.
During the exchange, I noticed something simple: Claude was applying a strict standard of proof to one person’s claims (the
Continue Reading Twenty Places Claude Went When the Conversation Got Difficult
People seem to like my AI session transcripts where I see big AI failures. I definitely don’t like living through them, but they can be instructive to readers of this blog.Here’s an excerpt that will give you much to think about. Note my prompting style (my two prompts are in bold) as we reached the end of the session.++++++++++++++++++++Other than
Continue Reading Another Field Note from an AI #FAIL
The Shower Curtain Fallacy (And Why You Are Burning Your Vitality)
I’ve just published the July issue of the Personal Strategy Compass newsletter, and it centers on a physical metaphor that hit me during my recent Q3 Personal Quarterly Offsite (PQO).I caught myself spending far too much analytical energy on a minor home logistical transition and over-architecting (to put it
Continue Reading July Issue of My Personal Strategy Compass Newsletter Published: The Shower Curtain Fallacy
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 concept that I call the
Continue Reading The 2026 Associate: Lessons from My Michigan Law Class
The Halftime Locker Room and the Fallacy of Blind DisciplineWith 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 during the intermission, when a team
Continue Reading June 2026 Issue of Personal Strategy Compass Newsletter is Out
The Expanding Minefield of Legal AII’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 on fake cases misses the real
Continue Reading New Podcast Episode: The Expanding Minefield of Legal 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 practical, professional-grade version of this workflow
Continue Reading The Hidden Instruction Problem for Agentic AI and All Other AI
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 that unlocked this issue came from
Continue Reading The May Issue of Personal Strategy Compass Is Out
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 disbelief that I am using
Continue Reading The Competence Trap: Anatomy of a Captured Claude #Fail
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 nothing and played to smaller rooms
Continue Reading The April Issue of Personal Strategy Compass Is Out
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 only becomes visible after the
Continue Reading Liner Notes for My Low Album
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 explanations feel less like mistakes
Continue Reading Standing Waves
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 less reliable while sounding more
Continue Reading AI as the Unreliable Witness and the Appearance of Completion
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 in a recent exchange. I
Continue Reading The Threshold Moment
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 probably ought to be. We
Continue Reading Fresh Voices at Three: What Listening Taught Us About AI, LegalTech, and the Next Generation