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Policy making within government is influenced by the leadership practices of those working within public administration. Through a case study approach, this study examines the perceptions of educational leadership practices of 14 former senior government staff who contributed to Student Success policy making in the Ontario Ministry of Education between 2003 and 2018. Using key government documents and informant interviews, this study is analyzed through Ontario’s Policy and Delivery Roadmap. Participants noted that meeting the needs of students as well as supporting a political agenda resulted in conflicting tensions, highlighting the importance of managing expectations, risk taking and perseverance to achieve shared goals. This study contributes to the limited knowledge base in public service educational leadership in government.