Collaborative evaluation brings community stakeholders and evaluators together with the opportunity to provide significant meaning to their work. In a community change initiative, collaborative evaluation also affords the opportunity to build community capacity. This article provides a framework for how collaborative evaluation can help achieve the goals of a community change initiative. The manuscript then explores one process dimension of collaborative evaluation — control over technical decision making — and explicates five dilemmas in its navigation. A case study is provided to illustrate the five dilemmas and to offer strategies for overcoming the pitfalls involved in the process of control over technical decision making. The article concludes with two primary lessons learned for evaluators trying to navigate the control over technical decision-making dilemmas in collaborative evaluation.