The purpose of this study was to examine the behavior and philosophical leadership characteristics of Millennial school district superintendents The following research questions guided the study: (1) What work environment characteristics do Millennial superintendents desire that lead to job satisfaction?; (2) What differences are there between Millennials' preferred work environment characteristics and previous generations' preferred work environments?; and (3) What suggestions and concerns do Millennial superintendents, board presidents, and administrative teams have about Millennial superintendent leadership behaviors? These research questions were examined through data collection consisting of interviews and focus groups. Interviews were conducted with four Iowa Millennial superintendents and their respective board presidents. Focus groups were conducted with the Millennial superintendents' administrative team members. The research concluded that Millennial superintendents in this study had a positive influence on the use of technology in their school districts, require support for their desire for work-life balance, and are making a shift in workplace norms and behaviors, but are able to adapt to the current system and board expectations. Furthermore, this study provided recommendations for school districts who hire or have hired Millennial superintendents and also details recommendations for future research. This study contributed to the body of research focusing on Millennials, public school superintendents, and K-12 educational 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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]