This exploratory study highlights certain differences in the way an expert and a novice engineer used their analyzing and generating skills while solving a fairly ill-structured design problem. The expert tends to use more inferences and elaboration when solving the design problem and the novice tend to use analysis that is focused on the functional relationship between the parts of the designed component. This difference might be attributable to the mental models or analogies that they generate. The mental representations used by the expert not only allowed him to go beyond merely predicting the performance of his conceptualization, but to also improve his solution by adding additional details that the novice, who because of his limited experience, was unable to add. The findings from this study would suggest that a proper grasp of systems concept is necessary to raise the problems solving ability of students to be reflective of experts. How components interrelate with each other and to the entire system, whether it be a simple or a complex system, are important for students to understand in order to increase their ability to generate conceptual solutions and solve functional issues. (Contains 4 figures and 3 tables.)