A system and method for improving outcomes in various person-to-person goal-oriented interactions is disclosed. Specifically, the method and system enable intelligent insights and recommendations to be presented to a facilitator of the interaction via a virtual assistant user interface. When the facilitator seeks to produce a specific goal with respect to the participant, the system can be configured to automatically generate, based on a series of inputs about the participant and previous interactions, intelligent recommendations that have a high likelihood of successfully promoting the target goal in the current scenario.