In an approach, a processor monitors messaging data between a plurality of users from a first collaboration application. A processor identifies an unanswered message within the first messaging data. A processor, subsequent to identifying the unanswered message, identifies that the plurality of users attends a collaborative session. A processor captures a second messaging data of the collaborative session. A processor determines that the second messaging data contains subject matter that meets a threshold of similarity to the unanswered message. A processor annotates the unanswered message.