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Dr. Curtis Cole is the Chief Information Officer (CIO) for Weill Cornell Medicine. He also practices Internal Medicine at Weill Cornell and New York Presbyterian Hospital, and is an Associate Professor of Clinical Medicine and Healthcare Policy & Research. Here, Dr. Cole discusses the role of CIO in a medical college and the perspective that brings to technology initiatives and the implications of teaching “digital natives” about digital technology, then considers lessons that we can take from past experience as opportunities appear as a result of new healthcare information technologies.