Superintendents, functioning as the local school boards’ chief executive officers, play a fundamental role in improving schools. While teachers and principals have been given a prominence in students´ learning outcomes, the perspective of superintendents as instructional leaders is often forgotten. Based on a nationwide survey of Swedish school boards the study investigates the boards’ expectations of their superintendents to influence student learning outcomes. The basic research question is: How may superintendents as boundary spanners facilitate school improvement? Boundary spanning is used as a theoretical and methodological framework to explore how superintendents may facilitate the local school system to become a more tightly-coupled system and strengthen the organization´s capacity of school improvement. The study’s findings indicate that superintendents have significant opportunities to influence political decisions and school improvement. Superintendents may exert an indirect instructional leadership and thereby tighten the couplings between different hierarchical levels in the school system. In their boundary-spanning roles, superintendents are expected to prioritize managerial assignments, which is a time-consuming task. Because the superintendent is not likely to be criticized or dismissed because of poor student results, windows of opportunities opens up in their entrepreneurial role, and thus a higher likelihood of working more effectively as instructional leaders.