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Adaptability is an important capacity for teachers’ effective functioning at work. We examined teachers’ adaptability and its links to three salient workplace experiences: teachers’ perceptions of autonomy support (PAS), well-being, and organizational commitment. We also examined two salient student outcomes: students’ achievement and their classroom-level PAS. With a sample of 115 high school mathematics teachers (and students from their classrooms), we conducted path analysis. Findings showed that teachers’ adaptability was positively associated with their PAS, well-being, and commitment. A significant direct association was found between teachers’ well-being and students’ achievement, and between teachers’ organizational commitment and students’ PAS. Indirect effects were also evident. The findings have implications for better understanding teachers’ responses to the inherently changing demands of their work.