The success of newly recruited medical school department chairs has become increasingly important for achievement of organizational goals. An effective onboarding program for these chairs can greatly facilitate early success, as well as satisfaction of the new hire with the position and the school. Onboarding programs can include traditional orientation items such as payroll signup and parking details, but should focus heavily on sharing organizational structure, culture, and how things get done. The goals of onboarding will be well served by implementation of three roles in the process. An Orientation Navigator can assist the new chair in the orientation phase, completing new employee documents and navigating the day-to-day challenges of working at the location. A Peer Mentor, generally a sitting chair, serves as both “buddy” and mentor, providing moral support as well as ensuring that the new chair gains an understanding of the people and processes important for getting things done. A Transition Mentor serves over a longer term as a sounding board and coach outside the peer group, assisting in a variety of ways to promote the chair’s growth, development, and success as a leader. Finally, any onboarding process is significantly compromised without the active participation of the dean, meeting regularly with the chair to clarify expectations, promote assimilation, and solve problems. Successful onboarding begins with a mindfulness of the needs of the newly hired chair, and a well-designed and well-implemented plan will have wide-ranging benefits for the chair and the organization.