Operating theatres experience dynamic situations that result from unanticipated developments in scheduled cases, arrival of emergency cases and the scheduling decisions made during the day by the operating room coordinator (ORC). The task of the ORC is to ensure that operating rooms (ORs) finish on time and that all scheduled cases as well as the emergency cases are completed. At the end of each day, however, ORs may finish too early or too late because cases have experienced delays or been canceled. Delays or cancelations add to the patient’s inherent anxiety associated with surgery and engenders anger and frustration. They have been shown to be an important determinant of patient dissatisfaction across the continuum of preoperative-operative-postoperative care. Recent research (Stepaniak et al. (2009) Anesth Analg 108:1249–1256) addresses how the risk attitude of an ORC affects the quality of the scheduling decision making. In this chapter you will learn about the interaction between the personality of both a human and an artificial OR scheduler, learn about the effects on the decision the OR scheduler makes and the quality of the resulting OR schedule. Therefore, we formalize risk attitudes in heuristics developed to solve the real-time scheduling problems ORCs face during the day.