Transferring knowledge from one part of the organization to another is an essential element of knowledge management and organizational learning activities. This study aims to facilitate knowledge transfer through human-watch interaction using a serious game. Although Smartwatch gaming, as an emerging gaming platform, is restricted by small screen size, it creates noticeable opportunities for game designers because smartwatches are attached to users most of the time. In this study, we describe the design of a smartwatch based serious game called iParallel. In this game, the users can decide on behalf of their parallel selves in the parallel worlds. The proposed solution includes a scenario authoring system that allows knowledge workers to create stories for their organization, and other workers can play these scenarios in iParallel. The study shows that a smartwatch game can facilitate organizational learning by providing knowledge workers the opportunity to experience different decisions’ outcomes.