The hiring of educators in medical schools (faculty who study the educational process and prepare others to become educators) has been one of the most successful educational innovations ever. Starting in 1954, through a collaboration between the Schools of Medicine and Education at the University of Buffalo, the innovation has spread to over half of the medical schools in the United States and to medical schools in several other countries. Practically every medical school and specialty now hires educators to conduct faculty development, evaluate learners, and develop or revise curricula. This article focuses on lessons learned by six-first-generation educators hired in medical education. These individuals made unique contributions that improved the process of educating and evaluating future physicians. Among their most important contributions have been the use of standardized patients, faculty development to improve instruction, and the use of clinical decision making theory. In addition, these professional educators created a home and career path for other professionals and nurtured proteges to continue the work they started. Ten lessons are reported from structured interviews using a standardized protocol. These lessons will hopefully inform current and future medical educators to help them sustain the effective collaboration between medical schools and educators.