The use of simulation in graduate medical education affords unique opportunities for increasing the quality of a resident’s educational experiences. Additionally, simulation poses a set of challenges that must be met to realize the full potential on learning and assessment practices. This article presents a methodology for creating simulation scenarios and accompanying measurement tools that are systematically linked in a direct and explicit manner to the Accreditation Council for Graduate Medical Education (ACGME) core competencies. This method, the Simulation Module for Assessment of Resident’s Targeted Event Responses (SMARTER), is an 8 step process that addresses the critical challenges of performance measurement in simulations and the need to document Accreditation Council for Graduate Medical Education core competency based learning outcomes. The SMARTER methodology is discussed in detail and 3 examples of scenario content and measurement tools generated with the SMARTER approach are provided. Additionally, results from an initial evaluation of the practicability and utility of the SMARTER measurement tools are discussed.