This article describes three challenges encountered during a developmental evaluation and explains how these were addressed from the evaluators' perspective. The evaluation was conducted to support the implementation of a three-year educational technology leadership project funded by the Alberta provincial government. The developmental evaluation responded to two purposes identified by the evaluation client: inform ongoing programmatic decisions and measure change in practice. The implications for evaluation practice related to the challenges of introducing a new evaluation approach, defining the boundaries of evaluator roles, and integrating technological resources are discussed and related to the Canadian Evaluator Competencies (Canadian Evaluation Society, 2010) and the Program Evaluation Standards (Yarborough, Shulha, Hopson, & Carruthers, 2011).