It has been a challenge to assess communication and professional values Milestones in emergency medicine (EM) residents using standardized methods, as mandated by the Accreditation Council for Graduate Medical Education (ACGME). This paper outlines an innovative method of assessing these Milestones using an established instructional method. EM faculty mapped the communication and professional values Milestones to an existing communication and interpersonal skills scale. We identified six communication-focused scenarios: death notification; informed consent; medical non-compliance; medical error; treatment refusal; and advanced directives. In a pilot, 18 EM residents completed these six standardized patient (SP) encounters. Our experience suggests SP encounters can support standardized direct observation of residents’ achievement of ACGME Milestones. Further effort can be made to create a tailored, behaviorally-anchored tool that uses the Milestones as the conceptual framework.