A computing system executes an instant message session between one or more users of the one or more collaborative tools. The computer system further examines information from instant messages in a message window of the instant message session. In addition, the computer system identifies keyword data of the examined information of the instant messages. The computer system queries a first repository for related content data that matches the keyword data. The computer system also generates one or more contextual search results based on the match. The computer system further transmits the generated one or more contextual search results for display on the one or more collaboration tools. The computer system further stores the keyword data and the contextual search results of the keyword data in a collaboration archive of a database, and automatically updates the contextual search results during instant message sessions.