Leadership in administration does not operate in a vacuum. Every decision comes with consequences for those tasked to make them, and foreseen career consequences, which often materialize during performance evaluations, may support or constrain administrators' leadership. This article explores how and why administrators factor in foreseen evaluation career outcomes when making leadership decisions, drawing from the qualitative investigation of 14 Canadian university decanal reappointments. The study asked 13 reappointed and one non-reappointed deans how they experienced and made sense of their reappointments. The study found that performance evaluations allow organizational agents to bypass normal role negotiation and that foreseen career consequences associated with evaluations play a role in leadership decisions. The effect of performance evaluations is contingent on personal, role, and evaluation characteristics. In the case of decanal reappointments, the short-term effect on individual leadership was modest. However, by limiting deans' effective in-role time, reappointments had an important long-term constraining effect on their consecutive and collective leadership.