This article emanated from a narrative inquiry into the stories of three Virginia gifted education coordinators whose years in service coincided with years of improved equitable representation in their gifted programs. By analyzing their experiences, the article sheds light on the organizational barriers they encountered. Organizational barriers developed from the system of relationships between district stakeholders and the subcomponents of the organization, creating an environment in which underrepresentation could flourish. Findings suggest the need for systemic solutions. Professional learning is implicated for all district leaders. For gifted education coordinators, professional learning experiences should strengthen their ability to discuss issues related to racism while helping them manage the multiple relationships complicit in underrepresentation. Recommendations for research and district reform are also suggested.