Department of Defense (DoD) program managers’ ability to make effective decisions is critical to a program’s performance. This qualitative study of two DoD program managers shed light into their decision-making processes in complex and chaotic programmatic environments. Additionally, this study specifically focuses on four aggregate categories—leadership, attitude, bureaucracy, and reputation. These categories have profound influences on the program manager’s ability to process information, make sense of a situation, and make decisions accordingly. By understanding how program managers perceive reality when facing challenges, we could potentially introduce necessary changes, adopt proven practices, and redirect resources toward efforts that would help program managers make more effective decisions.