This case study, framed within a school–university partnership, highlights the tensions inherent to employing design-based approaches for educational change. The case illustrates core tensions between an abductive, open-ended, design-based approach to change versus more traditional (deductive/inductive) approaches to managing change in schools. The design process serves as a way to break away from the traditional “grammar of schooling” (Tyack & Tobin) in a system unaccustomed to radical change. The case highlights the challenges of maintaining fidelity to the design process within a range of logistical and resources constraints, such as the time available to participants to engage in the process, and the difficulty of rapidly prototyping a new school model within an existing educational ecosystem. In the teaching notes, we recommend a theoretical lens and set of questions for educational leaders to reflect on as they consider approaches to educational change in their own settings.