This research study employed qualitative methodology, and the form of inquiry used was portraiture. Portraiture is rooted in the methodology of qualitative inquiry known as phenomenology; however, portraiture is distinct in that it intentionally includes diverse audiences through a fusion of art and science, while encapsulating the connection between sensory experiences and aesthetic values, bringing to light the beautiful portraits that convey rich and captivating stories (Lawrence-Lightfoot, 2016). The study explored the perceptions of Latina females in executive leadership cabinets and how building trust or mistrust potentially hinders female ascension into top superintendent leadership roles. The insights and perspective of female executive cabinet members in this study will inform future scholars interested in the interconnectivity of leadership, trust, gender, and the antecedents of trust. The superintendent's executive cabinet included assistant superintendents and executive-level directors. Participants were selected from school districts of varying sizes in the South Texas region. Map of South Texas with Cities and Counties (2020) identifies South Texas as regions south of San Antonio, Texas, including San Antonio. Therefore, four Latina executive cabinet members from school districts south of San Antonio, including San Antonio, were selected to participate in this study. Semi-structured interviews were the primary method of data collection, and photo-elicitation (Collier, 1957) was used to invoke conversation during the interview process to examine the social relationship between the superintendent and the executive cabinet through exploring perceptions of trust-building behaviors through interviews with Latina members of executive teams. For this study, the interviews were approached through a Latina feminist approach which allowed for authentic conversations, known as platicas, to celebrate and support the Latina population, extend both the researcher and the participants epistemology, and build trusting relationships as a process for change (Fierros & Delgado Delgado Bernal, 2016; Guajardo & Guajardo, 2013). The perceptions gleaned from these Latina female cabinet members' interview data were themed relative to various extant seminal trust theories as well as more recent studies examining which characteristics are common among the participants, while also being contextualized in the research literature on females and the superintendency. Those key themes included: (a) unreliability as an obstacle to trust, (b) teamwork, (c) concern for others, (d) developing relationships, and (e) transparency. [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.]