Measuring information technology (IT) investment payoff is difficult. This is because most of IT benefits are qualitative, indirect, and diffuse. To actually measure IT investment payoffs, tangible and intangible benefits factors as well as risks factors must be identified and evaluated. This research studies ten major evaluation methods, and available models that fall under each method, showing their advantages and disadvantages in handling the above difficulties. A road map to guide the decision maker in choosing the most appropriate methodology in his/her evaluation process is provided.