Direct observation has been recognized as a pivotal strategy in medical education to enhance the assessment and development of clinical competencies. This session aims to bridge the methodology used in the ACGME Faculty Development Toolkit—Improving Assessment Using Direct Observation—with the application of lifestyle medicine competencies. By equipping faculty and clinicians with tools to implement structured direct observation, we seek to enhance the integration of lifestyle medicine into clinical practice and education. The session will feature a combination of didactic learning, interactive discussions, and hands-on activities. Participants will explore methods for structuring direct observation, providing actionable feedback, and using competency-based assessments to foster and create a shared mental model for improvement. Special attention will be given to lifestyle medicine domains such as behavioral counseling, patient-centered care, and interprofessional collaboration. Attendees will also engage in role-playing exercises to practice the skills learned and receive peer feedback. This session is tailored for educators, clinical preceptors, and healthcare professionals seeking to enhance their teaching and assessment methods while reinforcing the integration of lifestyle medicine principles into patient care.