One important element of globalization is the dissemination of western educational ideals and organizational frameworks through educational development projects. While postcolonial theory has long offered a useful critique of this expansion, it is less clear about how educational development that eschews neo-imperialist tendencies might proceed. This problem poses a question that requires philosophical reflection. However, much of comparative and international development education ignores philosophical modes of inquiry. Moreover, as Libbrecht (2007) argues, philosophy all too often sees itself as synonymous with the Euro-American intellectual tradition, thus ignoring indigenous educational thought that might more appropriately guide local educational development. Drawing on John Dewey's (1938) call for deeper and more inclusive plans of operations in response to social conflicts and Jurgen Habermas (2008) call for "reciprocal learning processes" and "cooperative acts of translation," we will attempt to reach beyond our individual philosophical borders to explore the necessity and possibilities of comparative philosophy of education by sharing three examples of our current efforts to apply philosophical analysis to international educational development. These examples will articulate and embody the necessity and the challenges of applying philosophical analysis to educational development work. (Contains 4 notes.)