Leadership is a challenging task and leading well requires interpersonal skills that inspire those they lead to follow them. The aim of this grounded theory study is to explore the experiences of educational leaders who thoughtfully engage in trust-building and express vulnerability in their leadership practices. This study explored how six principals at kindergarten through 12th grade schools experience trust and vulnerability as building leaders. Three research questions guided this study: how do leaders experience trust, how do leaders generate trust, and how do leaders experience vulnerability. In this study, we begin by understanding the background to the problem and introduce the literature that provided a framework for this study. This study begins with an in-depth analysis of the history of trust research followed by how researchers have defined trust. Following the trust definitions, the literature explores the implications of trust in education and concludes with an overview of data on vulnerability in leadership and vulnerability in education. This grounded theory study was designed to explore vulnerability as means of improving trust is a topic that has not been extensively explored in education. While researchers understand the value of generating trust, not much is understood about the experience of vulnerability in education. Grounded theory provides an opportunity to explore novice topics to explore unknown theories. Grounded theory also provides the researcher with an opportunity to follow the research and explore what unfolds in data collection. By following the data as it emerges the researcher is able to further investigate themes that may be left behind in a traditional qualitative or quantitative study. Following the methods, data is presented from this study and concludes with implications and areas that require future research. The findings for this dissertation include trust as a significant influencer of Relational Trust theory and empathic leadership practices. I also present data that demonstrates the significance of expressing vulnerability as an educational leader. Much research has been conducted on the topic of trust, but little is known about how leaders experience trust, leaders looking to facilitate trust in their practice may benefit from understanding how other leaders experience trust and vulnerability in their role as 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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]