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Leadership style is one of the most important factors determining a school’s success, with Transformational Leadership being regarded as the most effective approach. However, little is known about whether teachers and principals perceive leadership qualities the same way. Based on quantitative research model this study examined teachers’ perceptions of the leadership styles of school principals and examined school principals’ perceptions of their own leadership styles. The purpose of the study was to determine whether there were discrepancies in perception between teachers and principals concerning the principals’ approaches to leadership. The research sample consisted of 451 teacher and 340 principals at public schools in Jordan, who were administered a questionnaire. Based on their responses, the study found that there are significant discrepancies between teachers’ perceptions of their principals’ leadership styles and the principals’ perceptions on their own leadership styles in a variety of domains. Individualized Consideration, Inspirational Motivation, Intellectual Stimulation, Idealized Influence, and Contingent Reward are among the traits most marked by discrepancies between teacher and principal perceptions. Ultimately, the study determined that principals view themselves as embodying a Transformational Leadership style whereas teachers perceive principals exhibiting traits associated more with Transactional Leadership.