Document Type
Article
Publication Date
2026
Abstract
The use of artificial intelligence (AI) chatbots is exploding. Adolescents increasingly prefer interactions with AI companions over peers. Adults rely on these systems for health planning, therapy, administrative assistance, nutrition guidance, and even simulated “romantic relationships.” Individuals and institutions are adopting AI tools at a pace that far exceeds the development of governance frameworks.
I developed Toby for use in my first-year Lawyering: Problem-Solving and Dispute Resolution (“Lawyering”) course to expose students to the dynamics of negotiating against an opposing counsel with a difficult personality—a type of adversary all too common in legal practice, yet difficult to prepare for. Toby is a negotiation chatbot designed, trained, and fine-tuned using materials developed specifically for my Lawyering course.
Toby functions as a practice tool, enabling students to build negotiation skills within the structured environment of a simulation. Critically, Toby operates according to the same legal tactics, strategies, and professional norms that I teach in class. These include core negotiation concepts such as anchoring, justification, specificity, and information bargaining. Toby is intentionally programmed to be difficult and uncooperative, thereby requiring students to respond in real time and to refine their ability to reach agreement and advocate zealously for their client—skills that are otherwise challenging to develop in the abstract.
Despite the promise that Toby and similar AI-assistants offer in both pedagogical and professional settings, their use gives rise to foreseeable problems, persistent governance challenges, and unresolved normative concerns. These include generation errors, the risk of overreliance, disclosure questions, opportunities for misuse, persistent concerns about analytical rigor and the appropriateness of AI in legal education. This Article considers foundational issues of AI governance through the specific case study of Toby, focusing on how real design choices expose predictable failure points and suggest possible responses.
At the outset, it is important to note that Toby, a bot used in the classroom as part of a role-playing exercise, represents a particularly favorable pedagogical application of AI in legal education. The use of Toby as a case study is intentional. It serves as a limited illustration of how AI tools may be deployed constructively in classroom settings. The example is intended to encourage instructors who remain skeptical of AI in legal education to consider controlled and creative ways to experiment with such tools when engaging with students.
Recommended Citation
Renee Henson,
My Negotiation Chatbot Toby and Pedagogical Governance, 32 Journal of Science & Technology 57
(2026).
Available at: https://scholarship.law.missouri.edu/facpubs/1385