This research explored the link between generational differences in preferred organizational culture and leadership styles within elementary and secondary schools. Using a cross-sectional survey of teachers in Pennsylvania, the study found no significant correlation between generational differences and organizational culture, however it revealed a significant relationship between transformational leadership and preferred organizational culture, highlighting how leadership profoundly influences the educational environment. Additionally, a notable disparity was identified between perceived and ideal organizational culture, suggesting areas for improvement that could enhance teacher retention and satisfaction. These findings emphasize the critical role of effective leadership in addressing teacher shortages, prioritizing leadership development to better align organizational culture with the expectations of educational professionals. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]