This paper discusses usability issues in the design of hierarchical menu systems in terms of the user's interpretation of the interface signs, or the menus. Focusing on the exploration of a particular functional item in the menu hierarchy, novice users' interactions with a computerized system are examined from the perspective of communicative breakdowns at first, and then the menu structure is evaluated through the information scent analysis. The former analysis investigates differences between the designer and the users in the basic assumptions for signifying or interpreting the interface signs, (i.e., menu texts and their organization for listing), especially on the 'peripheral' functions of the product. The latter analysis investigates the distribution of information scent in a menu list in order to obtain new quantitative clues for the assessment of whether the menu design is compatible with the users' naturalistic decision strategy or not.