The paper reports the main results and conclusions of the analysis of 8 dialogues between 1 expert and 8 novice users of Word. The analysis of the expert's requests for contextual information together with her explicit references to, and implicit use of the various types of contexts indicate that the the types of contextual information she exploits most are the progress of the current task execution, the software current state and the novice's current intention. Her help strategy, which differs greatly from standard didactic computer aided instruction approaches, encourages novices to adopt a "learning by doing" strategy through helping them to achieve the tasks which motivate their use of the software. This strategy relies mostly, for defining the informational content of help messages, on the short-term context and on a dynamic model of the novice's activities and goals, rather than on an individual (dynamic) or generic (static) cognitive user model.