This study aims to examine the relationship between school principals' 21st century skills and their strategic leadership according to teachers' opinions. In this quantitative research, a descriptive model that describes the situation was used. The study was conducted in Ankara, and 424 teachers joined the study. To get data from teachers, two scales were used: 21st Century Educational Administrators' Skills Scale and Strategic Leadership Scale. In order to determine the level of school principals' 21st century skills and their strategic leadership, descriptive analysis was used as well as Pearson Correlation Analysis and Regression analysis. There were significant positive relationships between all dimensions of educational administrators' 21st century skills and strategic leadership behaviors. Besides, education managers' 21st century skills were found to be a significant predictor of their strategic leadership behaviors. As a result of the research, it was revealed that information literacy, technology literacy, accountability, leadership and responsibility were significant predictors of managerial leadership behavior. School administrators need to increase their levels of knowledge literacy, technological literacy, accountability, leadership, and responsibility skills in order to improve their managerial leadership behaviors.