This study examined the relationships among the roles of college deans and conflict and ambiguity in deans' work. Challenges deans perceived as imminent in the future were also studied. The sample included 1,370 deans from 360 universities. They were asked about their roles, conflicts and ambiguities they faced, and possible challenges for the future. The responses show that deans are inevitably confronted with situations that require them to engage in roles that conflict with priorities that remain unfocused. They tended to identify challenges for the future as parallel to their current roles, suggesting that conflict and ambiguity will carry forward. The deanship as it exists today is enigmatic, and a major question centers on whether to fix the deans or the deanship. Professional development and training in time management may "fix the dean," but larger issues remain with colleges and universities that suggest that it may be time to fix the deanship through institutional responses that define priorities clearly. Shared leadership is a possible approach that may relieve some of the time pressures on academic deans. (Contains 5 tables and 41 references.) (SLD)