Purpose: The purpose of this paper is to investigate whether principals can have an impact on organizational learning (OL). The authors use a cultural perspective, based both in the emerging literature from positive psychology and the relatively well-developed research tradition in studying the nature and impacts of OL to address four questions: (first), is principal's cognitive trust in teachers' professional capacities related to knowledge sharing/OL among teachers?; (second), is principal's trust in teachers' professional capacities related to teachers' reports of being in a caring school setting (relational trust)?; (third), is principal caring related to knowledge sharing/OL among teachers?; and (fourth), is principal trust particularly important in school contexts with low income students? Design/Methodology/Approach: An existing database that includes principal and teacher surveys in 116 schools in the USA provides the basis for examining the four questions. Optimized scaling techniques were used to develop measures of principal trust in teachers' professional capacities, teachers' perception of principal caring, an indicator of academic support for students that includes a social justice of equity emphasis, and capacity for OL. The demographic characteristics of the student body and school size were used as possible moderating variables. The data were subject to both regression and path analysis. Findings: Principal trust was directly related to teachers' perceptions of principal caring, and indirectly related to OL. The measure of academic support for students had the strongest direct effect on OL. While the percentage of non-white students and school size had some relationship to OL, they do not change the overall results. The model, which supports the role that principals play in fostering both equity and OL is sustained when the authors examine student achievement. Research Limitations/ Implications: The limitations of the study stem largely from the nature of the sample and measures, which are confined to 116 schools in the USA, and a secondary analysis of a cross-sectional survey database. Because understanding the dynamics of a relationship-based/positive leadership perspective require detailed qualitative studies and longitudinal data, the results are presented as suggestive of issues that should be studied further. Originality/Value: Both trust and OL have been extensively studied both in education and other settings. However, few studies have simultaneously examined leadership, different types of trust and OL and none have done so in the context of positive psychology. The contribution of this analysis is thus empirical (extending the boundaries of what is known using concepts that are familiar) and theoretical (beginning the development of a theory of positive leadership that incorporates multiple factors associated with healthy and productive school environments).