Recent federal and state mandates have tasked school systems to move beyond principal evaluation as a bureaucratic function and to re-imagine it as a critical component to improve principal performance and compel school renewal. This qualitative study investigated the district leaders' and principals' perceptions of the performance evaluation process and criteria by which the effectiveness of principals was judged in a small, urban, New England school district. In an effort to assist the New England School District to create a more authentic principal evaluation process, district document analysis, literature review, interview transcripts and survey data were used to make recommendations to district leaders regarding four major themes including fairness, feedback, process and critical aspects. The themes were discussed in the context of schools as complex systems, where trust and distributive leadership drive school renewal. Emerging from the study of principal and superintendent perceptions of the process and criteria for evaluation, recommendations include: make principal evaluation an ongoing process; schedule time in each building; clearly identify criteria and supportive evidence; standardize rubrics and evaluation instrument; use evaluation instrument and feedback mechanisms that recognizes complexity of the principalship; provide meaningful feedback; and base summative evaluation on goals for personal-professional improvement and growth. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]