A computing apparatus uses an interactive user assessment test to identify and/or assess the need and skills of the user as part of an enrollment process for the user to register for the services of the system that provides real time communications connections between users and advisers. The advisers provide coaching services over real time communications connections provided via the system. A recommendation engine is configured to use the assessment results to recommend advisers for the user based on the need and skills of the user, as well as the real time availability of the advisers to provide the coaching services.