In Maldives, educational policy makers are beginning to explore the value of ICT and web tools as a medium of continuous professional development for school leaders and teachers. This paper reports on insights and responses of a group of five school leaders who participated in a web based distance education course. For most of them, this was their first experience in distance education as well as eLearning within a formal University context. By giving voice to the participants, we explore and identify strategies for successful first time eLearning experiences for school leaders. These include student preparedness for academic studies as well as for eLearning, language proficiency, cultural and social dynamics of knowledge construction as well as personal attributes which lead to successful learning.