A growing number of schools across the globe have implemented design thinking (DT) as an instructional approach to increase student engagement, motivate creative thinking, and teach students to problem solve. Although offering significant opportunity to students, implementing DT can involve pushing against the traditional "grammar of schooling." Drawing on in-depth qualitative case study data, we present findings on a previously low-performing, underenrolled middle school that underwent a dramatic shift when becoming a magnet school focused on DT. We explain the intentional leadership actions that facilitated structural and cultural changes, including building a collaborative leadership structure. Interactions between the principal and the teachers led to the emergence of practices that supported innovation schoolwide. At the same time, internal and external challenges rooted in the grammar of schooling arose, requiring educators to respond to sustain the momentum for change. Implications for policy and practice are discussed.