Despite many years of implementations, issues surrounding the success or failure of information systems are still shrouded in mystery. In a quest to improve business outcomes from such systems an IS analyst should have a key role to play. Organizational IS can be seen as a composition of indi-vidual and organizational learning processes, and as such is in a constant state of change. Knowledge as an individual sense-making process is a shifting sand of lessons learnt, experiential practices, active reflection and is therefore historically unique. Even when the balance of individual com-petencies, skills and attributes would seem to have been sufficient for the task at hand failure can still result from the combination of factors within that particular project. Organizational sense-making activities suffer from irrationalities of action, skilled incompetence’s and a plethora of organizational defence mechanisms. Within the information systems field, contextual analysis is an initiative focused on addressing issues of organizational information systems. Such systems are 'community' initiated, where system development or change activity is mentored by the analyst through the developmental mechanism of continual learning and communication.