Engineering education has a retention problem resulting in the largest proportion of students leaving the major during their second year. Most frequently citing poor academic performance stemming from a combination of course difficulty, poor teaching, and a lack of a sense of belonging, the second year has shown itself to be an important focal point for intervention efforts aimed at addressing these concerns. While university sponsored support efforts have been developed, the fact remains that oftentimes students elect not to attend, thus posing the question of whether or not the onus is on the students or the programs to engage the other. In an effort to connect these two parties regardless of circumstance, a video-based virtual mentoring intervention was developed and tested as a means to offer the benefits of in-person mentoring without the social inhibitors that prevent students from attending. This paper discusses both the development of a virtual mentoring tool as well as some initial findings regarding students' viewing preferences and outcomes of this type of interaction.