This article addresses issues of educational leadership in postcolonial and post-conflict environments. The focus relates to large-scale testing protocols, diversity in schools, asset-based community development, and communications technology. The article highlights the importance of context to the tenets of social justice, equitable human experience, and the right of all to have a meaningful and productive life. This article was originally presented as a keynote talk to the joint conference of the Canadian Association for the Study of Educational Administration and the Commonwealth Council for Educational Administration and Management.