The impression one might receive from reading many of the most popular books on leadership or management is that these activities take place in a vacuum. “When situation X occurs, try doing Y. If that’s not successful, consider doing Z as a fallback solution.” It sounds very systematic, almost formulaic—and utterly unlike what we actually experience as academic leaders. Perhaps the single most appropriate way to describe much of the work administrators do in higher education today is “messy.” Choosing between two equally deserving candidates for limited research funding is messy. Deciding not to renew a probationary faculty member’s contract is messy. Resolving the endless quarrels and conflicts that seem to afflict nearly every program we supervise is messy. And all those situations become infinitely messier when you approach them weighed down with the baggage of personal relationships.