The purpose of this study was to understand and clarify how the interactions of two important leaders, the superintendent and the principal, influence principal decision-making. Little is known about the superintendent and principal relationship and how that relationship influences site level decision-making, and ultimately influences student achievement. This study employed a phenomenological investigation with a specific type of phenomenology used, critical incident technique. The study was conducted using a variety of interview questions in which the perceptions of middle school principals were gathered. These responses were used to describe their experiences of superintendent and principal relationships and how those relationships influence principal decision-making at the school site. The questions asked the participants for responses that revealed their opinions about the relationship they have with their superintendent and how their decision-making practices were impacted by that relationship. Data collected for this study were categorized and analyzed through the lens of four significant factors that have great potential to influence the superintendent and principal relationship: trust, empowerment, vision, and communication. The major findings in this study were organized through the lens of each of these four factors, followed by two additional themes that warrant further consideration. By examining the four specific factors that are known to have the greatest influence on principal and superintendent relationships: trust, empowerment, vision, and communication, this study contributed to the educational literature on how superintendents can provide effective leadership to enhance the superintendent-principal relationship and promote positive principal decision-making.