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Unexamined and unjustified assumptions are the Achilles’ heel of development programs. In this paper, we describe an evaluation capacity building (ECB) approach designed to help community development practitioners work more effectively with assumptions through the intentional infusion of evaluative thinking (ET) into the program planning, monitoring, and evaluation process. We focus specifically on one component of our ET promotion approach involving the creation and analysis of theory of change (ToC) models. We describe our recent efforts to pilot this ET ECB approach with Catholic Relief Services (CRS) in Ethiopia and Zambia. The use of ToC models, plus the addition of ET, is a way to encourage individual and organizational learning and adaptive management that supports more reflective and responsive programming.