Markers that describe a user's actions are monitored in order to determine his or her level of proficiency with a user interface. A proficiency level is determined based on the markers. The proficiency level is adjusted periodically or in response to trigger events, to provide updated proficiency level information as the user becomes more experienced. One or more user interface features are automatically configured according to the detected proficiency level, so that the user is presented with an interface that is appropriate for his or her level of proficiency.