Errors will inevitably occur when one is involved in decision making tasks with complex, illdefined problems. Qualitative research on this topic has illuminated the complex nature of problems faced by many leaders and organizations as they make decisions. Although this research has answered many questions about the nature of errors, empirical research on errors among leaders remains scarce. To further explore this topic, 170 undergraduates were assigned to one of five work conditions and asked to read three cases with initiating structure problems and three cases with consideration problems while taking on the role of the CEO in the scenario.Errors committed by leaders were examined to answer questions about how work conditions influence errors committed. Additionally, how these errors influence performance outcomes was also examined. Results indicated that work conditions paired with errors made by leaders influenced levels of performance. Under certain conditions, most notably process overload, errors led to negative performance. We also discuss the implications of these findings for understanding the influence of work conditions on errors committed and their combined influence on performance outcomes.