Supervision, as this author discovered, is about building relationships with groups and individuals, as well as implementing policies and practices to create clear expectations. These policies, practices, expectations, and relationships should give rise to a work environment that encourages creativity, learning, and personal growth. In this chapter, the author reflects on her personal experience as a first-time supervisor and shares the challenges with which she was confronted and the learning that resulted from her efforts. She describes the role mid-level supervisors played in supporting her performance, learning, and skills as an early-career student affairs professional.