What happens to the implementation trajectory of a specific policy as it is shaped by multiple stakeholder understandings and competing policy influences in the school environment? The specific case in focus is the new government policy in South Africa on Whole School Evaluation (WSE). This policy requires that schools conduct internal self-evaluations, which will be followed by external evaluations and the implementation of school development plans for the purpose of bringing about school improvement. The purpose of this study is to explain how different stakeholders (education planners, teachers, and principals) understand and enact WSE policy within the school environment given the competing policy demands in the South African context. My study is unique for three reasons. First, I wish to cancel out explanations for possible policy failure that can be attributed to a lack of commitment to the new WSE. I will be seeking to understand how policy is implemented in contexts where there is a readiness to receive and manage change. Second, I will compare rival stakeholder understandings and trace the influence of these competing understandings on the implementation process and outcomes within the South African school context and, third, investigate how one policy is understood and acted-on, given the competing demands of related policies on schools and the practitioners working in the sampled schools. The specific research questions that guided this investigation are the following: 1. How do various stakeholders in the school environment understand WSE policy? 2. How do schools implement WSE policy given the presence of other evaluation related policies in the same school environment? Data was collected over a period of one year using a multi-method approach. Multiple methods of data collection included using in-depth, semi-structured interviews (both individual and focused group sessions) with stakeholders, observations of critical incidents in the policy implementation process, document analysis, photographs, teacher diaries, field notes, free writing schedules and structured questionnaires. The main findings from the study are the following: -- that when implementers are faced with multiple competing policies their implementation stance is determined by what is considered to be practical, immediate and known -- that for policies to have the desired impact there has to be a high degree of “coherence” among the different policies as well as “coherence” within individual policy frameworks. Furthermore, a combined and well-co-ordinated approach to multiple policy implementation is necessary for the policies to have the desired impact -- that for policies have the desired impact there has to be a high degree of “coherence” within the minds/understanding of practitioners -- that stakeholders who have negative experiences of a particular policy issue remain skeptical about the value of similar policies. Stakeholders draw on these experiences to guide their future actions -- that school-site conceptions of evaluations are constantly developed and changed as a result of multitudinous “forces of influence” -- that homogenous culture, bureaucratic responsiveness and hierarchical organization together compose a positive response to official policy -- that the course of policy implementation is influenced both negatively and positively by variables operating within and outside the school context. Finally the insights gained from this study hold practical as well as theoretical significance. Not only does it offer planning insights for the North West province in relation to WSE implementation, but is also serves to unpack the “black box” of policy implementation. It deepens our understanding of the problems faced with implementing planned change in transforming contexts even in cases where there is a receptiveness to change.