In this study I examined the obstacles and possibilities in using design thinking as a tool for building teacher autonomy. Design thinking, a human-centered problem-solving methodology which has been impacting the edges of educational reform for over a decade, is a potential tool for supporting school based continuous improvement. Design thinking is becoming increasingly common as a tool both for classroom learning and school improvement, but little research has been done on the impact of using design thinking as a tool for empowering teachers and helping them gain agency in improving both classroom instruction and the broader structures, policies, and procedures of a school. Data was collected over the course of three years on my experiences implementing design thinking as a leadership practice as school design practitioner. Between the fall of 2015 and the spring of 2017, I worked with teachers and staff to use design thinking to address different challenges faced by our school community. “Design sprints”—examples of design thinking-in-action—served as the basis for the analysis that is the focus of this dissertation research; the foci were: 1) Attendance intervention design; 2) Teacher led flexible scheduling; 3) The iterative design of our student conferencing systems. Three major findings emerged from my work. The first was that by learning and practicing design thinking, and more specifically, design sprints, teachers developed flexibility and adaptivity—they were willing to accept and support change efforts and the associated risks entailed in change. This second major finding, which was that teachers also developed self-efficacy and agency and were willing to take these risks in taking leadership of different aspects of the school program. Finally, this research found that while teachers did develop increasing confidence in their creative capacity, their capacity to maintain the mindsets and discipline entailed in an inquiry stance was sometimes limited both by the time allowed and pressured placed on a given design sprint.