Embodiments of the present invention address deficiencies of the art in respect to question and answer management in a collaborative environment, and provide a novel and non-obvious method, system and apparatus for synchronizing questions and answers in an instant messaging session. In one embodiment of the invention, a method of synchronizing questions and answers in an instant messaging session can be provided. The method can include maintaining an instant messaging session between first and second participants, identifying questions and answers in the instant messaging text, matching each of the answers to a corresponding one of the questions, and displaying the matched questions and answers supplementally to the displaying of the chat transcript, ensuring that a participant does not overlook a question where response on their part is required.