The principals’ personality and their leader behavior have been identified as a critical determinant of development of a school. Effective principals’ leader behavior for enhancing effectiveness of management warrants further exploration. The current study explores the relationship between the personalities of principals and their leader behavior. Based on the path-goal theory, the present research examines how leaders’ personality influences their leadership (directive leader behavior, supportive leader behavior, participative leader behavior, and achievement oriented behavior). The findings from 36 principals across 36 schools indicate that the principal’s personality trait of agreeableness will influence the directive leader behavior; additionally, the principal’s personality trait of conscientiousness will affect the participative leader behavior. Implications for practitioners are also discussed.