A method, system and computer program product for assisting users of a chat session to participate in the chat session. Messages of an instant message (IM) chat history are analyzed to determine the communication content. The key points of the IM chat history are then identified from the analysis, which are summarized. A first level of a hierarchical template corresponding to the determined communication content is identified, where the template corresponds to a general classification of the topic of the determined communication content. The template includes a recommended list of items to be discussed in the chat session that relates to the communication content. The template is loaded and then populated with information obtained from the analysis of the IM chat session, such as a summary of the identified key points of the IM chat history. The populated template will then be presented to the users of the chat session.