As a growing entity within higher education organizational structures, enrollment managers (EMs) are primarily tasked with projecting, recruiting, and retaining the student population of their campuses. Enrollment managers are expected by institutional presidents as well as through industry standards to make data-driven planning decisions to reach their goals. However, despite the availability of data, some enrollment managers revealed a different reality from traditional, rational decision-making models. This study explored the factors that contributed to or influenced the decision-making process of six enrollment managers working in either two- or four-year public colleges and universities located in the Midwestern United States. Interviews, including a word association exercise, documents and artifacts of tools utilized to make enrollment management decisions, and observational field notes were gathered and analyzed in this qualitative study grounded in constructionism.