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Systemic disruptions and uncertainties resulting from the prolonged COVID-19 pandemic have put extraordinary pressure on system-level educational leadership worldwide. Despite often being seen as drivers of thinking and change, system leaders had few, if any, precedents to draw from on how to lead effectively through such crises. This paper examines Ontario secondary school teachers’ (N = 17) perspectives on system-level educational leadership during the initial weeks of the COVID-19 pandemic and considers how these perspectives can inform future approaches to leading school systems through such uncertainty and disruption. Drawing on prolonged semi-structured interviews, six leverage points for systemic change are discussed: actors and elements, feedback, relationships and power, structures and roles, goals, and the overarching paradigm for teaching and learning.