Collective learning has been advocated to be at the source for innovation, particularly as serendipity seems historically to have been the driving force not only behind innovation, but also behind scientific discovery and artistic creation. Informal learning is well known to represent the most significant learning effects in humans, far better than its complement: formal learning with predefined objectives. We have designed an approach—ViewpointS—based on a digital medium—the ViewpointS Web Application—that enables and enhances the processes for sharing knowledge within a group and is equipped with metrics aimed at assessing collective and informal learning. In this article, we introduce by giving a brief state of the art about collective and informal learning, then outline our approach and medium, and finally, present and exploit a real-life experiment aimed at evaluating the ViewpointS approach and metrics.