Continuous improvement (CI) methods are growing in popularity around the world as approaches to leadership and educational change. There has been particular interest in using CI methods such as collaborative data inquiry to address racial inequities in schools. But these 'wicked' problems are, in many ways, more complex and uncertain than the kinds of problems CI methods were initially developed to address in the fields of manufacturing and healthcare. Drawing on contingency perspectives in organizational theory, we theorize that educators' level of uncertainty about the problem they are trying to address may lead them to adapt or modify CI practices. We explore this through two critical cases of school-based teams engaging in a CI process called Data Wise to address an issue of racial inequity. We find that the two schools varied in whether they viewed their problem of racial inequity as fundamentally uncertain, and these diverging understandings of the problem influenced to what extent they took a more straightforward or exploratory approach to engaging in CI. We discuss possible explanations for these findings and offer implications for scholars and educators who are working to adapt or enhance CI methods to promote educational change and better address racial inequities in schools.