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 “2026 Associate.” My goal wasn’t to teach students how to use specific software tools. Instead, we looked at how the next generation of lawyers will navigate an environment where AI is already the default, embedded reality.

Once again, I was reminded during the term that technology literacy is barely a footnote in traditional law school Professional Responsibility classes. This remains true despite its critical importance in practicing law today. I wanted to push these students to think past basic tech competence, which is just the baseline ethical requirement under ABA Model Rule 1.1 anyway. We focused on true technology literacy. That means understanding the strategic interplay of people, process, and technology from many angles so a lawyer can spot when an AI tool gets surface details right but completely misses what a client actually needs.

All throughout the course, we looked at issues from multiple perspectives, especially the client perspective. A true highlight of the class was bringing in JoAnn Stonier, the former Chief Data Officer of Mastercard. She spoke directly to the students about her expectations from outside counsel, what genuinely impresses her when working with associates, and the absolute necessity of understanding the client’s operational goals.

The core of our practical work culminated in the final paper. I required the students to turn in an AI-generated first draft, their final human-refined version, a redline comparison, and a short reflection on the assignment. The students all noted a fascinating initial reaction. When the AI first delivered the text, it looked almost finished. Then, they looked closer. They quickly realized that their own voice and style were entirely missing. Some of them said that they didn’t realize that they had their own voices and styles until they saw them missing in the AI drafts. The machine’s points were generic, vague, and semantically flattened. It made them want to rewrite the entire document.

The real revelation came through their final reflections, all of which were longer than I had asked for in the assignment. The students realized that traditional redlining and track changes are completely inadequate for AI-human text collaboration. Instead of showing clear, professional judgment, the redlines generated huge, illegible masses of marked-up material that were harder to decipher than just reading the two versions side-by-side. The traditional redline simply cannot capture the actual workflow of a human lawyer fixing a machine baseline. In fact, the written reflection itself became the true audit trail in a way that redlines never could.

I was also surprised by how organically the students adopted “red teaming” for their final papers. What started as an obscure strategic method that only the military veterans in the class had ever heard of quickly became the ultimate tool of choice for everyone. They began using adversarial prompts to force the AI to ruthlessly critique its own work before they even started editing.

Ultimately, I was incredibly impressed with these students, their work, and their sheer potential. Their personal reflections offered far more practical insight than a hundred standard industry white papers. The real story here was watching their profound perspective shift. They arrived on day one fearing that AI would completely eliminate their jobs. They left with a deep, confident understanding of exactly what the role of a human lawyer is and will likely be in the future. I have strongly urged all of them to publish their final papers, and I hope you start seeing some of their work out in the legal world very soon.

These are the 2026 Associates that I would want to hire if I had a law firm. Even more, these are the in-house counsel I would want to hire directly on graduation into a corporate law department.

You can (and should) listen to the full episode and learn more about the class here.

What are you doing to move your own team past ceremonial AI adoption and toward AI and technology literacy? How is your firm currently testing for true “technology literacy” during the onboarding process rather than just checking a box for baseline software competence?

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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