This article offers empirical data to explore ways that both industry mentors and academic internship coordinators support student interns in ways that optimize the workplace experience. Rich description of qualitative data from case studies and interviews shows that to optimize the internship, both the industry mentor and the academic internship coordinator ensure that the experience offers professional-level experiences while allowing students to make mistakes in the course of the learning experience. Finally, academic internship coordinators find it most effective to spend time selecting strong industry mentors, and then cultivating these relationships across years of internship interactions.