The transition for new head teachers (school principals) can be a difficult and unpredictable one. This article outlines a case of a deputy (assistant principal) in the United Kingdom as he takes up his first headship. We describe some of the challenges involved and prompt readers to consider strategies that could be used and support that may be accessed to negotiate this challenging period. In particular, this illustrative case shows how the lead-in period between appointment and formal assumption of the role can be productively used. This article would be of use to readers aspiring to take on a senior leadership roles. But it would also be relevant for people working at district level and others involved in recruiting, appointing, and supporting senior leaders.