This study explores school district leaders' strategies for managing the intersecting challenges of ambiguity, befuddlement, and contestation produced by the COVID-19 pandemic. Drawing on interview data from district leaders in the United States, the analysis is framed in existing research regarding how public administrators navigate competing values when making choices that have implications for 'how ought we to be?' in a given situation. We find that district leaders employed two strategies to manage these conflicts: (1) trying to focus on the expressed or inferred needs of political factions rather than the core disagreement and using personal and relational capital to manage disappointment and compromise; and (2) shifting the focus of leadership goals within the context of their original vision and core values. This study provides insight into both how educational leaders sort through value conflicts and the organisational implications of those processes.