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This paper presents the initial results of a study of the evolution of students' knowledge of software engineering from the beginning to the end of a master's degree curriculum in software engineering. Students were presented with a problem involving the initiation of a complex new project at the beginning of the program and again at the end of the program's formal coursework. After considering the problem each time, students were asked what questions they had as the senior software engineer, which software engineering processes need to be put into place, and to enumerate any other issues they saw. Statistical analysis indicates that their enumeration of software processes in the post condition is very significantly richer than in the pre condition. They also gave significantly more responses about requirements, design, and engineering management in the post condition. Qualitative analysis suggests that the students' questions in these areas were also more sophisticated in the post condition, suggesting, in accordance with the theory of "transfer as preparation for future learning," that they are moving along a trajectory towards expertise.