Leadership style plays an essential role on personality trait in educational systems. In this paper, we present a study among 180 school principals in city of Khomeinishahr, located in province of Esfahan, Iran. The study selects a sample of 123 principals and examines ten hypotheses including the effects of personality trait neuroticism, extroversion, resilience, participative, conscientiousness on leadership style. The study examined the effects of two groups of leadership, namely transactional leadership and Laissez-fair leadership styles on five personality traits. The results have shown that there were some meaningful relationship between transactional leadership and personality trait extraversion, resilience, participative and consciousness but there was not meaningful relationship between transactional leadership and personality trait neuroticism. In addition, while there were meaningful and positive relationship between Laissez-fair leadership style and personality trait extraversion as well as being resilience, our survey did not find any meaningful relationship between Laissez-fair leadership style and personality trait neuroticism, extraversion and being consciousness.