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Although there have been many calls to diversify the Ontario teacher workforce there has not been the same attention toward troubling the administrator diversity gap within publicly-funded education and its impacts on teacher hiring. Extant literature suggests that those responsible for making hiring decisions often hire candidates that resemble their own positionality. This conceptual paper is concerned with interrogating the administrator diversity gap and its impact on hiring within Ontario’s publicly-funded education system through an Applied Critical Leadership (ACL) theoretical lens. The paper will explore the current context of administrative demographics in Ontario, hiring policies that have contributed to the lack of BIPOC (Black Indigenous People of Colour) educators in permanent teaching and leadership positions, and gatekeeping mechanisms that hinder BIPOC candidates from accessing permanent teaching and leadership positions. This paper further contends that equitable hiring practices and representation cannot materialize without administrators engaging in transformative, critical self-reflective practice.