This study was conducted to determine the relationship between and among the leadership style of the principal, teachers’ job satisfaction and teachers’ retention in private institutions of the three selected private schools in the third congressional district of Davao City. The research instruments administered in this study were the Multi-Factor Leadership Questionnaire, Job Satisfaction Survey, and the Measure of Intent to Stay questionnaires. The descriptive correlational method was used in this study and the data were gathered using the questionnaires administered to the respondents. Based on the findings, it revealed that the principal’s leadership style had less significant drive to the critical decisions of the teachers on their job satisfaction and on their intention to stay in the private institutions. Not surprisingly, teachers take advantage of the relationship built among co-teachers and make use of their talents and time to support a desired conducive environment, in order to be effective in their teaching.