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Like artisans in a professional guild, we evaluators create tools to suit our ever evolving practice. The tools we use as evaluators are the primary artifacts of our profession, reflect our practice and embody an amalgamation of paradigms and assumptions. With the increasing shifts in evaluation purposes from judging program worth to understanding how programs work, the evaluator’s role is changing to that of facilitating stakeholders in a learning process. This involves clarifying purposes and choices, as well as unearthing critical assumptions. In such a role, evaluators become major tool-users and begin to innovate with small refinements or produce completely new tools to fit a specific challenge or context. We interrogate the form and function of 12 tools used by evaluators when working with complex evaluands and complex contexts. The form is described in terms of traditional qualitative techniques and particular characteristics of the elements, use and presentation of each tool. Then the function of each tool is analyzed with respect to articulating assumptions and affecting the agency of evaluators and stakeholders in complex contexts.