This phenomenological study sought to understand principals' lived experiences of being evaluated with reliance on the principles of developmental supervision and adult learning theory. Analysis of interview data from 16 principals revealed 3 major constructs in principal evaluation: evaluation is a complex, constantly changing system; principal evaluation is a year-long continuous process; and, effective principal evaluation is transparent, planned, and aligned with personal and system goals. Principal evaluation incorporated experiential and self-directed learning, and emphasized structure, collaboration, and ownership of the process by principals. Directive informational and collaborative interpersonal approaches were favored by principals and their evaluators. The findings contribute new knowledge about the phenomenon and have implications for reconceptualization and redesign of principal evaluation processes.