In this paper a prompt engineering model is provided based on the Tree of Thoughts (TOT) approach that helps IS educators generate engaging and context-driven teaching case studies. The TOT model proposed in the paper includes prompt types, flow, and sequence that will generate relevant, coherent, and consistent case studies. The prompt types used in generating collaborative teaching case studies are P1. Context and Structure, P2. Collaboration Framing and Reinforcement, P3. Benchmarking, and P4. Enhancements and Feedback. An illustrative outline of a case study that is generated by ChatGPT following the TOT model is provided. The collaborative structure of the case study is defined by following the disciplined agile methodology, practices, and principles.