This research identifies and establishes the most common and persistent obstacles faced by organisations in the development and implementation of knowledge management (KM) strategies, and strategic benefits that are realised. This study discloses a conundrum in the pattern in the maturity level of the KM initiative and simultaneous obstacles faced by the organisation at these maturity levels. This paper provides a background to the study, analysis of survey results, discussion and conclusion. Survey responses indicate both major themes and those that are lesser reported. The most common and ubiquitous challenge an organisation faces in the present time is the widespread lack of understanding of what KM is. Of only slightly lesser importance to that are obstacles within the organisational culture to effective implementation of KM, ‘commitment to cause’ and absence of formalised knowledge processes are major themes. Discussion further sheds light on the strategic benefits realised and attributed to KM. This research study findings may guide in examining theory and practice in the preparation and implementation of knowledge management initiatives.