This paper examines how a leadership preparation program, organized around a university-school district partnership in a small rural school division, attempted to facilitate improvements in Data-Based Decision Making (DBDM) and assessment literacy. The study used an inductive qualitative design which sought to capture the lived experiences and perspectives of research participants. This study highlights that building the capacity for data-based decision making and formative assessment is complex, involving building both individual and institutional knowledge in these areas, as well as strengthening the organizational supports needed to more effectively utilizing data to improve the instructional core.