A cross-national analysis was conducted to identify contextual influences that shape policies regarding the school-to-work transition and education-work linkages. The study's theoretical framework included principles based on technical-rational perspectives and neo-institutional perspectives. The study tested the following hypotheses: (1) schools are training grounds for employment; (2) individuals' employability skills and attributes are the foundation for collective socioeconomic benefits and well-being; (3) employable individuals possess theoretical understanding of work-related processes rather than work-specific skills alone; (4) making schools accountable to businesses and communities improves individuals' academic performance; and (5) school-work relationships, once institutionalized, persist and are maintained regardless of their actual technical output or original incentives. The study relied on comparative data from U.S. grade 12-equivalent student, teacher, and principal questionnaires from the Third International Mathematics and Science Study. Simple descriptive statistics, bivariate correlations, and multilevel multivariate regression were used to analyze and predict the nested relationships between students, schools and their communities, and relevant national-level factors. The analysis established that, although school-to-work transition policies and reforms have limited influence on the technical output of school-work linkages, they are legitimizing efforts that may still benefit the systems implementing them. (The bibliography lists 13 references. Two tables of descriptive statistics are appended.) (MN)