When analyzing the education process, and especially in technical disciplines such as engineering, the student orientation phase is one of the most important initiatives. The way in which students recognize, experience, and find meaning in the orientation activities is capable of orientating the subsequent development of student-oriented information and advice. This paper presents the research results from a three-year study at the University of Florence, followed along with more than 580 students enrolled in the Mechanical and Management Engineering undergraduate programs. To gather greater insight into students’ previous experiences, decision-making processes, information searching patterns, and participation in institutional orientation experiences, a comprehensive questionnaire was designed. The results indicate how critical intrinsic motivation and individual interest in engineering, plus expectations about employment prospects, were in shaping students’ academic decisions. There is evidence of changing trends in students’ motivation when compared across the years, and the increasing significance of family in academic selection. In addition to identifying suggestions for improving online based information, incorporating alumni narrative experiences, and reinforcing relationships between schools and universities, this study demonstrates the capacity of perceptions analyses to enhance orientation practices. These insights may help organizations to develop stronger and more versatile orientation programs.