The purpose of this qualitative interpretative phenomenological analysis study was to examine the experiential perspectives and perceptions on how leadership styles and values of millennial principals impact the school environment, specifically looking at interactions with culture and climate. Trait Theory and Generation Cohort Theory were used as the theoretical frameworks. The sample included six millennial leaders who all worked as public-school principals, preK-12, across different school districts in the Midwest. In-depth semi-structured interviews, both in person and via phone, were conducted to unveil each principal's unique and connected experience as a millennial principal. The major findings are organized by the following themes: natural leadership, self-disclosure, one room schoolhouse, jack of all trades and personal connectedness. The results of this study provide insight and implications for school and district communities including parents/guardians, teachers/staff, and district leadership. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]