In this article, Annick Janson and Robin Janson introduce research from the Microsoft New Zealand's Partners in Learning Programme by documenting the impact of digital learning objects (DLOs) on educational practice. Janson and Janson describe the impact of DLOs on the teaching practice of a primary school in New Zealand, tracing the effects of the project from individual teachers and classrooms to the institution as a whole. The authors focus their findings through the prism of educational leadership development, exploring how changes in teaching practice can be accelerated by illustrating what types of changes are needed in schools at the organizational level. Fundamental to this transformation, they argue, is overcoming the challenges currently faced by school principals. Janson and Janson discuss their development of a DLO designed to assist principals in educational leadership development.