This article shares the findings of a qualitative case study examining the experiences of teacher leaders as they engaged as teacher evaluators alongside school principals. Data collection included observations and interviews with four teacher leaders and three school principals to answer these research questions: (1) What TDEM structures have supported instructional improvement within ESD? (2) How have teacher leaders navigated the implementation of the TDEM? (3) How do teacher leaders support and evaluate career teachers within the TDEM? Findings from this study contribute to what is known about the ways that engaging teacher leaders in the teacher evaluation process can positively influence the meaning and purpose of evaluation for teachers.