This document is offered as a resource for academic institutions--especially independent colleges and universities--that intend to hire and support "pioneering" presidents. To start with a simple definition: by "pioneering" CIC means presidents who are the first people to bring specific, sometimes but not necessarily visible, and institutionally relevant identities to the role. This is not meant to be an exhaustive statement of the challenges that pioneering presidents face, nor a definitive guide to hiring and supporting such leaders. Think of it as a toolkit: a collection of hard-won, practical advice from presidents and board chairs who have already blazed new trails. The toolkit includes advice about defining the role of a new president, especially one who breaks the traditional mold at a given institution; the hiring process itself; the announcement of a pioneering president; preparing the campus and, if necessary, piloting a new campus culture; onboarding procedures; support during the first year of a new presidency; and ongoing support from the board of trustees and other stakeholders. The resource also includes a series of guiding questions that board chairs, trustees, pioneering presidents, and others might want to ask at every step, from the first inclination to hire a pioneer through their inaugural year as president and beyond.