During the 2017-2018 academic year, the authors co-supervised a building of 29 resident advisors (RAs) and approximately 1,000 undergraduate students in a large residence hall. To ensure that this community is successful each year, Housing & Residence Life (HRL) at Virginia Tech places two full-time professionals in this residence hall. This achieves two goals, the first being adequate student staff to supervisor ratio and, second, a strong presence of professional staff in the community to connect and build relationships with the students. Supervision of student employees is a core competency of the student affairs profession, according to the American College Personnel Association and national Association of Student Personnel Administrators (2015). Supervision experiences are often solitary; one entry-level professional supervising a crop of undergraduates. Yet, a co-supervisory experience may be becoming more common. A co-supervisory experience is where two entry-level professionals provide oversight and supervision jointly. In this article, the authors reflect on their co-supervisory experiences and share case studies that will make supervision both familiar and strange.