Purpose: This dissertation explores how experienced educational leaders, operating under the Every Child Succeeds Act (ESSA) and its systems of accountability, articulate and navigate tensions between their personal conceptualizations of education as an economic good and the dominant perspectives within their organizations, shaped by broader systemic demands. Theoretical Framework: The study is grounded in four perspectives of education as an economic good: education as a product, education as an investment, education as a service, and education as an identity. Each perspective includes distinct public goals, processes, outcomes of interest, and the essence of the good and measures. Methods: Using criterion-based purposive sampling, four participants from various U.S. regions were selected. Data collection involved interviews, document analysis, and reflective journaling, analyzed through the lens of the "Competing Conceptualizations of Education as an Economic Good" framework. Data Analysis: A two-step methodology guided the analysis. For the first set of research questions, the four conceptions of the theoretical framework were used as themes to code and identify both leaders' and organizations' conceptualizations. To explore how leaders navigate tensions arising from conceptual misalignment, thematic coding was applied to uncover patterns and strategies in decision-making processes. Findings: Leaders and organizations exhibited diverse but dominant conceptualizations of education, which often led to tensions described as a "push or pull." These tensions were most notable with education as a product, where measures towards educational goals are grades and test scores. Leaders employed two main strategies to address these challenges. The Trojan Horse Strategy involved outwardly aligning with organizational priorities while embedding personal values into broader goals. The Floor is Lava Strategy focused on avoiding areas of misalignment "hot spots" and prioritizing "safe zones" where personal and organizational priorities aligned. Implications: In the cases of conceptual alignment, the leader's efforts were catalyzed. Improving alignment between leaders' and organizations' conceptualizations can enhance organizational synergy and outcomes and provide valuable insights for leadership practices and policy development.