Generating talking points on behalf of a user and providing the talking points to the user is provided. Talking points can help users to quickly and easily start a personalized conversation that enables participants of the conversation to make a connection, thus eliciting better communication and collaboration. Talking points can be generated based on commitments or requests identified in a previous conversation, anomalies or patterns identified in context data, or information items of interest collected from various data sources. One or more top-ranking talking points are surfaced to the user to help the user start a new conversation or to continue a previous conversation.