A tenured respected principal learns that supervisory relationships with staff are only one side of the leadership coin. The other side turns up when a new assistant superintendent is assigned as his supervisor. Problems are imminent when the supervisor seems ready to usurp the principal's traditional decision-making authority. The principal, as the subordinate in this scenario, ponders the role of loyalty and team play versus the political implications of supervisory conflict and pressure from a parent interest group. Questions guide current and aspiring principals to reflect and consider the facets of establishing a relationship with a new supervisor and resolving practice-related conflicts. Activities are designed for reflecting on the pitfalls and possibilities open to a principal under pressure from the supervisor, band parents, reallocated resources, and his own struggle with fair and appropriate treatment of a valued teacher he has known throughout his high school career.