The inception of a new head marks a challenging transition for the independent school community. Though little has been written on it, numerous programs exist to help heads prepare for and assume headship. In contrast, scant attention has been given to the transition of the spouses and children of heads. However, two other kinds of "first families" face similar challenges: congregational clergy and college presidents. The literature regarding the families of these professionals closely parallels the information gleaned from interviews and discussions with independent school families. This article examines: (1) Why trustees ought to attend to the needs of the first family. (2) The environment into which the head enters as well as the kind of person who is drawn to headship and the nature of the job. (3) It articulates the challenges of being the first family. (4) It examines how boards can ensure a good match between the needs of the first family and the school.(5) Finally, it delineates the steps that boards can take to ensure a smooth transition for the "first family."