James MacGregor Burns (1978) stated that leadership was one of the least understood phenomena in the world even though it was one of the most studied. This lack of understanding was even more prevalent when high school leadership development was examined. At present, a knowledge deficit exists between research and practice, as individuals responsible for training the next generation in leadership lack a comprehensive understanding of contemporary leadership theories (Newman et al., 2019). This study uses a phenomenological approach to find the commonalities or the essence, as Van Manen (2016) described of the high school experiences of seven community leaders in Midwestern City. Midwestern City is a mid-sized city with a major university in the central United States. These community leaders were chosen from varied backgrounds, interests, and careers to find experiences that were perceived to be impactful to a diverse group of leaders. This study's findings indicated that during high school these community leaders had a diverse group of friends, were identified as leaders by adults, and focused on interpersonal skills. From these commonalities, it was evident that the leaders' experiences most closely aligned with the newer relationally driven leadership theories than with the individualistic leadership theories developed prior to the 1950s. These findings will be useful to guide sponsors, coaches, college professors, administration, and district office personnel in their efforts to enhance the effectiveness of leadership training programs. Consequently, there is a need for further investigation into the impact of leadership training provided to educators on the development of student leaders. [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.]