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Abstract With emerging innovations in artificial intelligence (AI) poised to substantially impact medical practice, interest in training current and future physicians about the technology is growing. Alongside comes the question of what, precisely, should medical students be taught. While competencies for the clinical usage of AI are broadly similar to those for any other novel technology, there are qualitative differences of critical importance to concerns regarding explainability, health equity, and data security. Drawing on experiences at the University of Toronto Faculty of Medicine and MIT Critical Data’s “datathons”, the authors advocate for a dual-focused approach: combining robust data science-focused additions to baseline health research curricula and extracurricular programs to cultivate leadership in this space.