Elements of game play, such as usage statistics, scores, levels, challenges, achievements, competition, and the like, are incorporated into a productivity application to assist in motivating users to learn features of the productivity application. A recommendation system is utilized to assist users in determining what features of the application to learn next. Help content that is associated with the productivity application can also be tied to the features that are currently being learned and used by the user such that the linked help content is readily available. Users may compare their scores and compete with other persons that are also participating in the game play learning system.