Despite many decades of school reform efforts aimed at improving educational outcomes through accountability measures focused on academic performance, systemic change in America’s schools and substantial improvements in student preparation to participate in a complex, global society have not been realized. The state of Kansas is attempting to change this through the Kansans Can School Redesign Project (KCSRP). The purpose of this qualitative case study was to examine the perspectives of key stakeholders on how a midwestern middle school undergoing redesign is engaging in the process of changing its system based on the school’s redesign goals and principles. A theory of organizational learning underpinned the study and provided insight into how participants viewed their school’s capacity to learn to implement a change process to pursue new practices associated with KCSRP. The study’s conclusions included looking at the findings through the lens of Peter Senge’s disciplines of a learning organization. The implications of the study include considerations for school leaders and policymakers considering systemic change initiatives along with considerations for future research.