A computing system for managing a multi-modal communication session in an enterprise is disclosed. The computing system includes a monitoring module for monitoring activities associated with the multi-modal communication session between a customer and an agent, wherein the customer and the agent communicate over a first communication modality. The system further includes an analysis module for analyzing the activities to initiate communication between the customer and the agent over a second communication modality within the multi-modal communication session, wherein the communication over the second communication modality operates along with the communication over the first communication modality. The system further includes a notification module for generating notifications for notifying information associated with the first communication modality, the second communication modality, or a combination thereof to a supervisor.