Critical success factors and how they influence successful implementation of technological innovations have received significant attention in extant literature. Comparatively fewer attempts have been made to define the yardstick for determining the outcome and the magnitude of “enablers” of the implementation process of technological innovations. The empirical aim is addressed through survey and case study of comparable number of IT projects. The knowledge acquired from the empirical and theoretical investigations is used to develop an “interactive framework” aimed at creating an understanding of the things an organisation does to enable innovation, the “enablers”, and what an organisation achieves, the “results”. The prerequisites are defined in an assessment context to interact with the most profound “disenablers” from our findings (failure of senior management to lead; technology has outpaced the sophistication of the user community to properly utilise the tools, particularly in the sense of enterprise deployment; delivery of less functionality that originally planned; integrator cost out of control, etc.) and thereby discover the need for leadership and involvement. Furthermore, the interactive framework provides the tools required to get senior management properly engaged in the initiative and thereby significantly raise the potential for success.