The paper presents the current winds of change that are blowing within the University of Botswana (UB) in pursuit of implementing elearning. This transformation was triggered by both internal and external influences in higher education.  Among others, there is need to transition towards institution-wide deployment of on-line learning strategies to enhance the educational experience. The UB commissioned an external consultancy in 2007 which among others recommended that, “the university involvement in distance learning should be confined to online learning programs...”  The UB embarked on a pilot project namely the Masters in Project Management. Unfortunately, the project failed dismally due to many factors including: “top-bottom” approach; lack of a comprehensive institutional strategic plan; the absence of situational analysis of the environment to scan the environment regarding resources; facilitator attitudes and user preparedness. The author recommends use of the Leadership, academic and student ownership and readiness (LASO) model which seemed appropriate for this endeavour because it integrates top-bottom and bottom-up initiatives which incorporate leadership with academic to promote ownership and readiness among stakeholders.