While counselors do gain knowledge on advocacy in their educational program, little is known about how school counselors communicate and advocate in their relationships with principals. The purpose of this study was to seek clarity on how school counselors describe their experience in their relationships with school principals as they communicate and implement self-advocacy. The research question for this study is, how do urban area counselors describe their experiences with communication and self-advocacy with principals? The methodology utilized is a generic qualitative inquiry, with the interviews taking place via the Zoom platform. The sample for the study consisted of 11 urban area K-12 certified school counselors with active memberships with a professional school counseling association. Data was collected by interviewing all 11 participants. Participants responded to semi-structured interview questions to provide knowledge of their experiences. To analyze the data, inductive thematic data analysis was applied with open and axial coding processes. The focus was on understanding how school counselors communicate through advocacy efforts. Two main themes emerged: communication is authentic and open and self-advocacy must be strategic. Three subthemes also emerged from the data: being heard/supportive open relationships, setting of boundaries, and utilizing a plan of action. School counselors reported a description of their experiences in communication and implementing self-advocacy efforts in their relationships with school principals and provided applicable information for the field of counselor education and supervision. Recommendations for future research involve a mixed method approach of generic qualitative and quantitative inquiries looking closely at the practicum and internship supervisory experiences of self-advocacy strategies of school counselors. [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.]