Despite improvements in gender equity within higher education nationally, underrepresentation in women's leadership persists in Christian higher education. As women in leadership navigate the context of member institutions of the Council for Christian Colleges and Universities (CCCU), characteristics of evangelical culture (e.g., theological views of gender, traditional gender role expectations) may at times impede these relationships across gender; however, some evidence has suggested that women who attained a presidency within a CCCU institution have identified male advocates to be influential in their leadership journeys. The purpose of this study was to examine the experiences of men who had been identified by women presidents of CCCU institutions as having been advocates in their leadership identity development and journeys. This article explored the findings of a hermeneutic phenomenological analysis of data from interviews with 14 male participants nominated by women presidents of CCCU institutions across North America. The findings of this study centered on three themes: (a) the pursuit of theological congruence, (b) gender blind, the double bind, and being first, and (c) pragmatism and persuasion. Based on these findings, the interdependence of organizational culture, self-awareness, and the social construction of a leadership identity through reciprocal relationships was discussed. Implications for practice include recommendations for evaluating institutional contexts and personal biases, as well as cultivating reciprocal relationships between women and men.