A system for providing coaching includes a system that creates a user-specific coach to assist a user in achieving one or more goals, such as, e.g., a financial goal. The coach is generated based on one or more traits of the user to increase the likelihood that the user will relate and respond to communications from the coach in a manner that enables the user to achieve his/her goal. The traits used by the system to create the coach can include traits input directly by a user, as well as user traits deduced by the system by monitoring various types of user behavior, including the user's usage of computing devices, habits, etc. The system also adapts the coaching provided by the coach in response to trends noted by the coaching system as the system is used by the user as well as others.