Critical thinking has long been recognized as an essential cognitive skill for academic success and lifelong well-being. However, schools continue to face challenges in effectively promoting and teaching critical thinking skills across all student populations. This study explores these challenges and investigates strategies for fostering critical thinking in all students, beginning with the attitudes, willingness, and expectations of principals and teachers. Specifically, it examines how teachers’ current and future expectations of their students’ critical thinking abilities relate to teachers’ self-efficacy in teaching critical thinking, teachers’ and principals’ growth mindsets towards students’ critical thinking abilities and willingness to promote critical thinking, as well as principals’ current and future expectations for their students’ critical thinking skills. To analyze these relationships, a series of regression analyses and Hierarchical Linear Models were conducted on a sample of 366 teachers and 32 principals in Broward public elementary schools. Findings revealed that teachers’ self-efficacy and growth mindsets were significantly associated with their current and future expectations, although not with their willingness to promote critical thinking. Among principals’ factors, only principals' current expectations showed a significant association with teachers' current expectations. These findings suggest that fostering positive attitudes among teachers may be a practical and effective approach to enhancing their expectations for student development in critical thinking. Nonetheless, given the importance of principals’ attitudes highlighted in other studies, further research is warranted to explore the role of principals in promoting critical thinking in greater depth.