Education
Bailey enrolled in Oxford University in history, eventually changing to art history, and eventually receiving a doctorate of philosophy in art history from Oxford. He was awarded a fellowship to the Getty Museum"s paintings department in 1983 that he found so significant that he decided to pursue museum work instead of academic work. He later went on to enroll in Columbia University"s Center for Curatorial Leadership, which Bailey credits with shifting his aspirations from the curatorial to the directorial.
The Center exposed him to his first formal training in management techniques, and exposed him to the idea that active curators with skills in management, finance, strategy, and diplomacy could play important roles in the future of their institutions.
Near the end of his program at the center, Bailey held at a residency at the Louvre, closely observing its director, Henri Loyrette. Bailey credits his experiences at Columbia"s Center of Curatorial Leadership with his decision to change career paths towards a directorial one, especially his experiences in shadowing Loyrette.