A contact center agent coaching tool may employ systems and methods comprising receiving a communication involving a participant, analyzing the communication in at least near real-time relative to a receipt of the communication using a computer-based communications analytics facility for at least one of a language characteristic, a non-word symbol, or an acoustic characteristic, analyzing the communication in at least near real-time relative to the receipt of the communication using a contextual analysis to obtain a context, determining at least one of a category or a score associated with an aspect of the communication using the at least one language characteristic, non-word symbol, acoustic characteristic, or the context, and triggering a coaching tool to be presented to the participant based on at least one of the category or the score.