It is widely known that gender bias persists in male-dominated fields. Gender bias is often defined as acts that position one prototypical social group over another (Begeny et al., 2020; Gloor et al., 2020; Roberts & Brown, 2019; Scheifele et al., 2021). It is unknown how male superintendents mentor women while established in their superintendency at public school districts in the United States. The specific problem is that gender bias is a cultural construct expressed by both men and women, and research to date does not explore men's role in positively solving gender bias challenges alongside women inside and outside the education field. The purpose of this qualitative, inductive grounded theory study is to uncover the processes by which male superintendents mentor women while established in their superintendency at public school districts in the United States since 2015. Twenty-seven superintendents were interviewed between October and November 2023 concerning their cross-gender mentorship experiences as mentors. Findings for this study included (a) male superintendents demonstrated varied awareness regarding how females experience gender bias in the leadership domain and (b) participants lacked formal mentorship training. Future research is recommended around what ways to male superintendent mentors and their female mentees perceive overt and covert biases perpetuated upon female mentees differently. Those who hire superintendents should be daring enough to make loud and intentional identity choices in their educational CEOs that represent their student populations while maintaining the highest of leadership standards. [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.]