The reliance on information systems, Internet, and networking technology and infrastructure has made Information technology (IT) become the fundamental elements in many areas. That's why organizations that pursue success are highly anticipated to invest tremendously in attaining flawless IT implementations. In ensuring the IT spending made a wise decision, necessary steps were taken to perform vital evaluations of the IT investments beforehand. Varieties of evaluations available, with different approaches adapted to different style of organizational preferences. Nonetheless, the essential part of it is the expectations of returns or values. Once the investment has been made, the achievement of the returns and values indicates the successfulness of the IT investment spending. But not all cases of IT investments end with success stories. Many have ended contrary to what organizations have expected. Lesson learned, studies have recommended to couple the evaluation aspects with enablers of IT investment success or success factors. This paper reviews the current literature regarding the IT investment evaluation approaches and proposes an Ishikawa diagram that describes the factors that influence the success of the IT investment. In this paper, six factors of IT investments enablers are discussed which are Financial, Internal, External, Strategic, Technological, and Risk.