As Indigenous peoples employed at a university who are working to Indigenize it from within, in this article, we share our experiences, discuss some of our challenges, and show how we draw meaning and strength from Indigenous stories to ground us in our approach. We use Indigenous, anti-oppressive, anti-racist and decolonizing theories, Indigenous standpoints, embodied experiences, and emotive responses to make explicit the lived work realities of Indigenous people in mainstream universities. Through a dialogic approach, we trace one pathway for explicating Indigenous transgressive leadership in Canadian universities. In our discussion, we situate Indigenizing work as "willful work" (Ahmed, 2014). We call for a "strategic willfulness" as a constructive orientation, for Indigenous leaders to embrace, as we continue to confront the colonial, hetero-patriarchal and whitestream nature of Canadian universities. Most importantly, we underscore the need for Indigenous leaders involved in Indigenizing work in the university to draw from Indigenous epistemological and relational ethics in their leadership work, and to be strategically willful, interruptive and transgressive.