Legislative attempts to enforce systematic program evaluation in schools in the United States since the adoption of the 1965 Elementary and Secondary Education Act (ESEA) have had limited success. Due to challenges unique to the professional culture and climate of schools, implementation of mandatory evaluations has been met with varying degrees of resistance. This study seeks to understand some of the obstacles impeding the implementation of systematic program evaluation in today’s schools. While schools within a system may seem the same—in appearance, formal structure, and processes—differences do exist. One difference is the organizational climate of schools or the distinguishable internal characteristics that influence the behavior of its members (Hoy, 2011). The present study seeks to understand whether there is a relationship between the organizational climate of a district and the perceptions and attitudes of school principals and teachers with regard to program evaluation. An online survey was administered to principals and teachers of four Massachusetts districts. This survey included newly developed items assessing principal and teacher efficacy, awareness, and attitudes toward program evaluation. Additionally, the Organizational Climate Index (OCI), developed by Hoy (2002), assessed the openness and health of school relations through the measurement of aspects of climate at the institutional, principal, teacher, and student level. Analysis of survey data revealed all four districts fell into the below average range for Collegial Leadership (CL) and the above average range for Institutional Vulnerability (IV). Multivariate Analysis of Variance (MANOVA) results suggest a strong main effect of district. Pearson correlation coefficients suggest a positive correlation between teacher confidence in school program evaluation and Collegial Leadership (CL), a moderate positive correlation between teacher self-efficacy (data analysis and supporting school goals) and Professional Teacher Behavior (PTB), and a moderate negative correlation between teacher confidence of school program evaluation and Institutional Vulnerability (IV). Definitions provided by survey respondents regarding what program evaluation is, reveals that teachers (n=46) demonstrate weak understanding of program evaluation while administrators (n=5) demonstrate moderate understanding of program evaluation. Findings from this study may be used to inform both evaluators’ and educators’ professional development and practice, increase the utility of evaluations, and increase accountability and student achievement.