Graduate medical education has undergone a dramatic evolution from a time-based process to a competency-based system, aiming to produce a physician workforce to further the quadruple aim in healthcare while embracing innovation in clinical medicine and residency education. Resident evaluation in a competency-based system is grounded on workplace assessment of a resident in the authentic clinical environments in which day-to-day resident education occurs. The Accreditation Council for Graduate Medical Education (ACGME) has created a framework for workplace assessment of resident performance using the ACGME milestones. The Individual Learning Plan (ILP) is a personalized roadmap that outlines each FM resident’s learning objectives and goals based on ACGME competencies. As residency leaders, it is our task to determine if residents are prepared to independently practice medicine without direct supervision. A robust residency evaluation is at the core of evaluating and attesting that residents have met the requirements needed for program promotion.