Educational leadership is a field that historically has not been closely examined in the Yukon Territory. The generation of Yukon-specific theory therefore remains difficult, particularly given the historical absence of an Indigenous cultural lens through which to examine educational leadership. This is the central argument presented by this paper. Employing research from Yukon's southerly neighbour, the province of British Columbia (BC) as a basis for comparison, the manner in which educational leadership may be constructed, developed, and enacted by practitioners requires a fundamentally different approach in the Yukon, given that a number of Yukon First Nations, representing many Indigenous people, have settled land claims and established self-governing agreements with the Canadian and Yukon Territorial Governments. These factors pose specific challenges, resulting in variations and adaptations to the way that education is provided and how educational leadership may be constructed and enacted in this northern Canadian Territory.