System and method for coaching based on workout history and/or readiness/recovery information. Improved solutions enable intelligent management of a user's personal fitness journey based on workout recommendations that closely align with the user's traits. In one exemplary embodiment, workout data for a population of different individuals is analyzed to identify groups of similarly performing individuals. Each group of individuals is analyzed to generate an expected profile that approximates the physiological and/or psychological traits of the group. An expected profile includes heuristics and/or performance metrics that enable dynamic coaching during workouts. Subsequently thereafter, users can be dynamically coached by their client device, based on the expected profile.