This case presents how the leadership team and faculty of a small, independent school used design thinking to respond to a competitive marketplace and desire for enrollment growth in the middle grades. The new middle school head came in with a mandate for substantial change and sought to engage all stakeholders in a process of redesign and program renewal. The case describes how leaders involved the school community in the Design Thinking protocol to solve intangible design problems. It explores leadership challenges presented by this approach, including strategies to address these challenges.