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Despite policy changes on educational leadership in Canada, studies demonstrate a disconnect between what is covered in principal preparation programs and how principals perceive their ability to work with diverse learners. Six current school leaders in Ontario, Canada who successfully completed Ontario’s Principal Qualification Program were interviewed to understand their perceptions on the program’s ability to prepare them to lead. Each participants racial experiences and identities shaped their definitions of equity and understandings of difference. Study findings indicate critical areas of change for principal preparation: training guidelines, preparing equitable leaders, and educators’ perceptions on their preparedness to lead. CRT in Education and Applied Critical Leadership frame analysis and support the need to integrate culturally relevant practice into leadership preparation programs.