Techniques are provided for ranking the entities that are identified in a document based on an estimated likelihood that a user will actually make use of the annotations. According to one disclosed approach, usage data that indicates how users interact with annotations contained in documents presented to the users is collected. Based on the usage data, weights are generated for features of a feature vector. The weights are then used to modify feature scores of entities, and the modified feature scores are used to determine how to annotate documents. Specifically, a set of entities are identified within a document. A ranking for the identified entities is determined based, at least in part, on (a) feature vector scores for each of the identified entities, and (b) the weights generated for the features of the feature vector. The document is then annotated based, at least in part, on the ranking.