This paper proposes a method of project management knowledge transfer in order to increase the success probability of R&D projects. Our method consists of knowledge externalization and knowledge internalization. "Structured project analysis" is a method of knowledge externalization that reviews a finished project and produces a structured project case. "Internalization workshop" is a method enabling managers to internalize the project management knowledge based on the analogical transfer approach. The method selects success and failure scenarios (future chance and risk items) from the structured project cases that have some similarities to the ongoing target project. Then, the method prompts the managers to imagine and analyze future scenarios of their target project by analogy and take action concerning them. We apply this method to an ongoing business-academia collaborative project in which Toshiba, Shimizu Corporation, and the Japan Advanced Institute of Science and Technology (JAIST) are developing an innovative healthcare information system. We qualitatively evaluate the effectiveness of the proposed knowledge transfer method and show how to fill the project management knowledge gaps among project team members drawn from business and academia.