While most students-as-partners case studies have focused on partnerships between students and faculty, this case study outlines a collaboration between a student-led organization and an educational development unit at the University of Virginia. We turn the lens inward and consider the challenges involved in enacting an ethos of "radical collegiality" (Fielding, 1999) in this unique partnership and our work with training student consultants. We describe the evolution of our collaboration, the programming we developed, and what we learned in the process about sharing power and expertise while negotiating the interests of our respective organizations. We describe our discovery of how deeply institutional norms and academic power structures shaped our perceptions, experiences, and habits. And, using the analytical framework of threshold concepts, we explore our rocky navigation of issues of trust, vulnerability, and role confusion as we moved towards a clearer understanding of and appreciation for the limits of our different types of expertise.