Prior research has highlighted strong benefits from having a collaborative environment within schools. However, there has been limited research regarding factors that can promote a collaborative relationship between two key professionals within the school environment: school administrators and school psychologists. The first purpose of this study was to examine the nature of collaboration between school psychologists and school administrators. The second purpose was to explore ways to facilitate and improve this interprofessional collaboration within the school to promote safe, equitable, and supportive school climates and positive student outcomes. Using a qualitative research method, we collected and analyzed data from three focus groups: school psychologists, school administrators, and a combined group of school psychologists and school administrators, all working in New York City and nearby suburban, public culturally and linguistically diverse school settings. We developed an interview guide disseminated to the participants before the focus group meetings which were held via conference call and recorded. Discussions were transcribed and analyzed using content analysis. Four raters coded the data and reached consensus on major themes. The findings suggest that quality collaboration between school psychologists and school administrators is infrequent and often haphazard and it should instead be intentional and purposeful. The study uncovered prerequisites for and challenges to effective collaboration, leading to recommendations for intervention in school practice and in preparation programs with a goal of enhancing school climate and student outcomes.