This paper explores the student achievement-related decision-making processes of eight school principals in Ontario, Canada. First, we describe Ontario's public education system with respect to neo-liberalism and student achievement. Next, we review general approaches to reducing the achievement gap as it pertains to matters of race. We then show how these eight Ontario school leaders make decisions to reduce the achievement gap within their respective schools. This decision-making process is influenced by considerations such as economic conditions, learning styles and school-based or individual solutions. While it is acknowledged that principals do not operate in isolation, our study focuses on the high level of responsibility principals are vested with in order to provide leadership for student outcomes, while taking other factors into account within the decision-making process.