Decision-making practices of school superintendents have previously been studied in the context of decision-making in response to a program or initiative, identifying decision-making styles, and ethical decision-making. Administrative mindfulness provides the construct to explore the cognitive mindset of superintendents as they make decisions. Prospect theory provides the conceptual framework to explore the process used by superintendents as they frame decisions, determine reference points, and evaluate options based on those reference points. The qualitative research design of this study employed semi-structured interviews as the primary method of data collection. Cross-case analysis was used to highlight variations in the data and to identify patterns within the data. Findings in the study referenced the substantial influence deferring to experts by superintendents played during their decision-making as they gathered information about a dilemma, determined their reference points, and evaluated options. Each school superintendent in the study provided definitive cognitive processes used in his decision making reflecting attributes of administrative mindfulness. When discussing a decision of regret, each subject identified an absence of at least one attribute of administrative mindfulness. Reference points, in the decision-making processes of superintendents, were discovered to be value-laden and unique to the superintendent rather than being quantifiable as situated in behavioral economics. However, reference points in both superintendent decision-making and behavioral economics provide a tool for evaluating various options and assessing risk. The study concluded that the overlay of administrative mindfulness on a school superintendent's decision-making process provides multiple opportunities to enhance decision-making. Those improvements to the decision-making processes are dependent upon the management of a superintendent's ego, a commitment to deferring to experts, and cognitive effort on the part of the superintendent to seek improvements in his decision-making practices.