Public school literacy leaders have complex roles and responsibilities associated with their positions, including being literacy advocates. The purpose of this qualitative study was to explore the factors that contributed to district reading supervisors? perceptions of advocacy. Participants included five district reading supervisors in the state of Virginia. Using grounded theory design, a series of three rounds of interviews with each participant yielded data related to intrinsic and extrinsic contextual factors that influenced how district reading supervisors and school-based reading professionals worked to meet literacy needs in K-12 settings. Results indicated that past experiences informed both roles and dispositions. Supervisors and reading professionals used their roles to support others in meeting students? needs. Professional and personal dispositions influenced the ways in which literacy leaders negotiated relationships with literacy stakeholders, particularly principals. These extrinsic and intrinsic factors subsequently influenced the ways in which district reading supervisors perceived and enacted advocacy. Discussion includes a substantive theory of advocacy in literacy leaders, questions warranting further study, and implications for teacher educators, school-based administrators and educational policymakers.