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Although the demand for IT outsourcing (ITO) has increased recently because of the recent recession, concerns about business discontinuity in the transition phase cause companies to hesitate to adopt ITO. Therefore, a guideline to improve the prospects is needed. However, studies on the success factors of the transition phase in ITO are lacking. In this study, we develop an expert hierarchical value map (HVM) of the success of the transition phase in ITO by using cognition scientific methodologies. We empirically verify how success factors affect the success of the transition phase. Specifically, we derive an HVM of main stakeholders by using in-depth interviews and approaches, such as repertory grid technique (RGT) and laddering, based on means–end chain theory. We validate the success factors empirically through a bipolar analysis of RGT. Finally, we determine the most important cluster of success factors through cluster analysis.