In this integrative literature review, we synthesize the scant literature from the last 40 years of educational research on how school principals make difficult decisions. Reviewing 15 peer-reviewed articles, articles were coded for the methods used and their substantive findings. We review sampling techniques, the types of problems and methods used to elicit and capture decision-making performance, and the statistical and qualitative analyses conducted. The substantive findings cover five main themes: a decision-making model, differences between novices and experts, personal characteristics, decision-making skills, and general findings about the overall construct. The article concludes with directions for a research agenda.