The COVID-19 pandemic created an unprecedented disruption to education and schooling at the end of the 2019-20 school year. Operating in a context of great uncertainty, education leaders were tasked with making key decisions with potentially far-reaching impacts on the educational and mental and physical health of students and families. Drawing on 9 cross-sectoral focus groups with school board administrators, representatives from education industry partners, and K-12 educational policy research organizations, this paper provides a historical record of the evolution of decision-making and points to promising lines of inquiry and lessons that can be learned from this moment in education.