Have you ever wondered why certain leaders are more popular than the others among their workers or followers? What really influences one’s leadership style? Does personality trait of an individual influence their leadership style in anyway? Well, these are the questions that this study conducted in Pune city among the English medium school administrators strives to answer. The purpose of this study was to identify the personality types and leadership styles of the administrators of four selected English schools in Pune city, India. Then derive a relationship between their leadership style and their personality type. It also determines the ways in which the school teachers classify their respective administrators leading style. Rating scale, questionnaire, interview and observation were used as the instruments for this study. After the analysis of the collected data, the conclusions confirmed that the personality type of a leader does influence his or her leadership style.