The August issue of my Personal Strategy Compass newsletter is now available: “The Night Watchman: Converting Solitary Anxiety into Strategic Leverage.”
This issue grew out of something I started noticing in my own solitary planning blocks. Once I removed the usual operational noise and created some real white space, my analytical mind did
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
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
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
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
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
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 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 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
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
