A demographic time bomb is ticking in many school jurisdictions. Up to 70 per cent of present leaders in the private and public sectors will retire within the next five to ten years as the "baby boomers" move on. While succession planning has become a major initiative in the private sector, leadership succession in education tends to hew to old paths. Where are new educational leaders to come from? How should their succession be orchestrated? The traditional source of succession at the secondary level, the department headship, is no longer an attractive route for many teachers. Many potential leaders do not perceive the role of principal or assistant principal in a positive light. These roles are increasingly being associated with managing the standards/standardization agenda with which many professionals profoundly disagree. While it is premature to declare a leadership crisis in education, it is not too early to call on policy makers to attend to the growing need for succession planning at all levels in education. Based on an examination of change over times in four schools in Ontario, this article addresses issues of leadership succession in education and, more precisely, examines the influence of principals' succession on the principals themselves and their schools. (Contains 1 figure and 2 notes.)