Though women are overrepresented in education as classroom teachers, they continue to be underrepresented in decision-making leadership positions in education administration (Bynum, 2016; Coleman, 2003; Fuller, 2013; Grogan & Shakeshaft, 2011; Moorosi, 2018; Robinson et al., 2017; Torrance et al., 2017). The cause of the low representation of women in decision making has been attributed to a wide range of reasons spanning from ingrained patriarchal mindsets, societal biases, lack of professional networks, misconceptions of women in leadership, and the lack of leadership opportunities. Other causes of gender inequality in educational leadership are linked to a lack of a systematic mentorship ecology and infrastructure within institutions. Instead, there are hegemonic structures of White males in power who mentor other White males to continue the cycle (Robinson et al., 2017; Shakeshaft, 1989). It is a challenge in the Catholic church because traditional beliefs rooted in conservative Biblical interpretation may support and reinforce male domination in leadership contexts. The steady shift of society’s values and understanding of women, however, has revealed the growing acceptance of women as leaders in other industries beyond education, which contributes to a deeper understanding of leadership styles and how leadership can be androgynous. This study analyzed the experiences of current assistant superintendents or superintendents in a Catholic diocese. Experiences ranged from participants’ early days as teachers, administrators, and assistant superintendents or superintendents. This phenomenological study explored participants’ lived experiences with faith, spirituality challenges and barriers, and navigating relationships and accomplishing goals through transformational leadership.