This qualitative study investigates how different types of work experience shape principal sense-making of new teacher evaluation policies and systems. The U.S. state of Michigan is a timely state to study this phenomenon as Michigan has experienced significant changes to its teacher evaluation policy and system, tasking principals with making sense of these changes. Data come from 12 public elementary school principals and includes interviews (N = 36), observations of principal evaluative practices (N = 24), and additional teacher evaluation documents. Three primary findings emerged after an analysis of the data: years of experience as a principal, years of experience at one school, and years of experience as a teacher shape how principals make sense of and ultimately enact teacher evaluation policies and systems. Implications for policy and practice are discussed.