An electronic apparatus and a controlling method thereof are provided. The controlling method according to an embodiment includes acquiring contents and storing the contents in a memory, identifying a first section of the contents related to a first behavior by analyzing the stored contents, outputting contents of the identified first section, acquiring a user image captured while the contents of the first section is output, identifying whether the first behavior is completed by analyzing the user image, and based on identifying that the user has completed the first behavior, outputting contents of a second section, the second section being a next section of the first section.