Abstract: Video-Reflection is a common approach to realize reflection in the field of executive coaching for professional development, which presents a video recording of the coaching session to a coachee in order to make the coachee reflectively think about oneself. However, it requires a great deal of time to watch the full length of the video and is highly dependent on the skills of the coach. We expect that the quality and efficiency of video-reflection can be improved with the support of computers. In this paper, we introduce INWARD, a computational tool that leverages human behavior analysis and video-based interaction techniques. The results of a user study involving 20 coaching sessions with five coaches indicate that INWARD enables efficient video-reflection and, by leveraging meta-reflection, realizes the ameliorated outcome of executive coaching. Moreover, discussions based on comments from the participants support the effectiveness of INWARD and suggest further possibilities of computer-supported approaches.