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This paper takes up the essential question of how school leaders work to introduce teachers to innovations in education. The purpose of this paper is to present findings from a qualitative comparative case study of two U.S. schools that place Design Thinking (DT) an innovative instructional approach to education at the core of their theory of action. This study examines the actions and dispositions of school leaders in supporting DT and discusses implications for educational change. Both principals recognized and communicated the values of DT, established structural supports, and addressed cultural aspects of change. However, their approaches varied in key ways that led to school wide support for DT in one setting, and waning support in another.