Work-shadowing is an under-researched aspect of leadership development. This paper places workshadowing in the broader context of responses to the challenges of managing leadership succession in schools, drawing on an evaluation of a pilot shadowing programme for aspiring primary headteachers. The paper identifies a number of key themes in prospective heads' experience, namely those of transition, capability and identity. It shows how a shadowing programme can address these if appropriate "rules of engagement" are established and if processes are put in place that enable the shadowees to "frame" their experience in relation to both the rationale for the day-to-day interactions of headship and the broader structural and cultural contexts within which headship takes place.