This study expands on the findings from an NSF (GSE 0827490) funded study entitled "Pathways to Self-Efficacy and Retention of Women in Undergraduate Engineering" which investigated reasons for low representation and retention of women in STEM fields. In this paper, we report on qualitative analysis from a recent pilot study involving in-depth interviews from five engineering students in their final academic year of study and a set of five engineers interviewed within eighteen months of commencing their first full-time job in an engineering career field. All subjects previously completed several terms of cooperative education (intensive work study) within the same agency.Interestingly, all five of the newly hired engineers interviewed strongly believed that their cooperative education (co-op) experience had helped prepare them for full-time employment. Additionally, all strongly conceded that these experiences specifically helped ease the transition from student to professional. Although three out of five agreed that their college courses provided them with technical skills they could use in the engineering field, only two felt as though they had adequately developed the soft skills in college that they needed for full-time employment. Notably, all mentioned that their co-ops provided opportunities to meet and work with active role model(s) which aided in the development of self-confidence.All five of the engineering students graduating within the next academic year who were interviewed mentioned that in general co-op at least partially hindered their academic performance. They cited a positive experience with employers and the knowledge that they had likely secured a full-time job upon graduation as the reason for a decrease in academic drive. Impressively, all five students stated that their co-op experiences increased their perceived level of ability to be successful in their work roles. It is worth noting that although it was not specifically asked of them, at least three of the ten interviewees mentioned the difficulty they experienced during the transition between co-op and school. This paper will delve into the findings of this initial pilot study and will draw reasonable conclusions from the data. We also gathered information about which types of interview questions are helpful in gaining useful insights into how cooperative education impacts retention in undergraduate engineering programs and a student's transition to full-time employment following graduation.