The viability of any system depends upon its decision-making and ability to adapt to change. Superintendents, serving as the CFO of their school system, must be able to make ethically sound and fiscally responsible decisions that will ensure the success of their organization. This thesis examined leadership roles and responsibilities of Vermont superintendents undergoing school consolidation and governance changes in their districts. Specifically, the study explored the involvement of stakeholders throughout the merger and budgeting process; the role of leadership at multiple levels; the politics and values behind decisions; and the contextual differences between communities and stakeholders as influencing consolidation and fiscal planning. The interpretative phenomenological study utilized one-on-one semi-structured interviews with participants to collect data, and through the incorporation of the Theory of Bounded Rationality, sought to address a gap in the literature related to the intersecting variables that impact school leaders' decisions. Five themes emerged from the analysis of the data, which revealed that superintendents were able to successfully navigate mergers and build unified budgets through the development of deliberate structures in their unique contexts. Recommendations for current and future school leaders committed to guiding their communities through consolidation, as well as suggestions for future research, are also offered.