The literature on Information Technology (IT) investment decisions argues that organizations decide to invest given the expectation of an adequate combination with other internal resources will develop non-imitable organizational characteristics. However, it seems to be much more ease to state than accomplish. Some emblematic non-success cases of implementation involving organizations proficient in the IT best practices stimulate a more careful analysis on the real mechanisms behind this achievement. In this article, we present the results of a multiple embedded case study research conducted in organizations knowledgeable in managing IT to generate business value and discuss why some organizations achieve results better than others do. Our analysis indicates that IT investment decisions effectiveness, in fact, is related to the ability of managers to identify previous economic inefficiencies in business dynamics and mitigate them by applying the TI, something that is not achieved by using the current techniques.