This chapter consists of three sections on becoming a medical school dean. It is written through the lens of three Latina/o/x/e, Hispanic, or of Spanish Origin+ (LHS+)-identified deans in three individuals in different stages of their careers with different experiences. Dr. Jose Manuel de la Rosa was the founding dean for a new medical school and served in the role of campus leadership for over 30 years. Dr. Olga Rodríguez de Arzola is a female Hispanic dean of a medical school in Puerto Rico, founded in 1977, and has been in the role for more than 13 years. Dr. Pedro José Greer Jr. is the designated founding dean for the new Roseman School of Medicine in Nevada. The first section describes the motivations for those who wish to be the dean, describes some traditional and nontraditional trajectories into the dean’s office, and includes the role of the dean in the school of medicine, the pathways to the dean position, and the skills required for the dean. It delineates some formal dean training opportunities, discusses the advantages and disadvantages of each one, and finally discusses how to capitalize on informal training opportunities. Some personal reflection exercises are included to facilitate participation. The second section discusses how a Latino leadership style is different from traditional leadership and might be specifically advantageous to bring a revolution in the medical education environment. The third and final section includes three personal stories from a former dean, a current dean, and a designated dean to be. The chapter is certainly not designed to be the authoritative guide to being a medical school dean as much has been written on this topic, but in keeping with the objective of this book simply delineates some thoughts to consider on a personal level before seeking this career route.