As senior student affairs administrators (SSAAs) seek to lead effectively in higher education, some SSAAs consider spiritual resources to enhance leadership practice. Yet, empirical literature on the intersection of spirituality and leadership in higher education is relatively absent and needs to be deepened and broadened. The purpose of this study was to examine the intersection of spirituality and leadership among SSAAs. Guided by a constructivist epistemology, this grounded theory included the following research questions: (1) what can be learned about how spirituality influences the leadership practices of SSAAs when the intersection of spiritual and leadership development is considered; (2) what are the critical influences on the process by which spirituality informs the leadership practices of SSAAs; (3) how, if at all, do the spiritually-guided leadership practices of the SSAAs in this study influence the organizational environments of their institutions; (4) how, if at all, are the spiritually-guided and value-laden leadership practices of the SSAAs in this study challenged by the socio-cultural environment of the academy pertaining to values, spirituality, and religiosity? Data sources included two interviews with a sample of 14 SSAAs. The grounded theory, "Walking the Labyrinth: The Process of Leading with a Spiritual Orientation among Senior Student Affairs Administrators," emerged from the data analysis. One core category and four key categories emerged from data analysis. The core category, "leading with a spiritual orientation," describes the pervasive nature of spirituality within the leadership process, and the relationships between spirituality, values, and leadership, which form a "core" that facilitates congruency in decision-making for spiritually-oriented SSAAs. The first key category, "sustaining a spiritual outlook," describes how spiritually-oriented SSAAs develop a spiritual outlook on life and apply this outlook to their leadership. The next two key categories describe characteristics of leading with a spiritual orientation: "catalyzing spirituality to maximize leadership capacity" and "prioritizing people in leadership practice." The last key category, "'managing your identity': navigating the academy's socio-cultural environment" describes the context for the process of leading with a spiritual orientation. This grounded theory has implications for future research and theory development, for SSAAs, and for student affairs practice. [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/en-US/products/dissertations/individuals.shtml.]