In the last two decades, Ethiopia has seen a proliferation of community-level development projects that are either led or funded by international entities; however, it is the local arms (e.g., country offices (COs)) who are often responsible for the implementation of the development projects. I argue that these COs are the middlemen in the local-global development interface as they work directly with the community while also adhering to standards and policies set by their international overseers. In the Ethiopian education sector, these foreign entities can be leading anything from tutoring services and after-school programs to full-blown alternative education centers. Educational leadership as a field of scholarship has focused primarily on, (1) within-country educational leadership hierarchies, and (2) public or private (first and second sector) education. In this study, I characterize and explore educational leadership that, (1) transpires transnationally (where the leadership hierarchy crosses national boundaries), and (2) occurs in the third sector (specifically, within international nongovernmental organizations (INGOs)). Drawing on Michael Burawoy's extended case method, I use ethnographic techniques to investigate educational leadership within country offices of three INGOs in Ethiopia to explore ways the global community shapes and is shaped by the local education for development efforts it deploys. I find that the CO leadership practice is plagued with challenges, such as feeling disconnected from both their local and their global associates, government- and community-level corruption, lack of confidence in speaking English, and headquarters (HQs) that are both physically and culturally distant from Ethiopia. The CO staff's Ethiopian identity played a significant role in their experience, as it did mine in the research process. The CO staff found power in their local knowledge. They used their native tongue to create boundaries from the HQ when they needed, their cultural competency to find informal channels of communication through which to translate HQ demands to local practitioners better, and their rapport with communities to discreetly bend and break the rules. The INGOs provided resourced, smaller-scale, flexible alternatives to supplement the public sector but in doing so, at times threatened, instead of strengthening, it. Different issues become salient for INGO programming experiences in Addis Ababa versus its surrounding rural areas. The outskirts of Addis Ababa, however, often mirrored rural communities more closely than the inner city. COs are transnational educational leaders working beyond the boundaries of schools, creating linkages with the local and the global but also between the public and third sector; however, the much more substantial structures of power asymmetry at the global and national level have significant impacts on their experiences. I discuss implications for educational leadership, international development broadly, and policies to guide local-global partnerships in education for development. I also explore my reflexive process and experience in the research process as well as its methodological implications. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]