A key challenge for districts is creating a pipeline of principals who are prepared to serve as instructional leaders. The assistant principal position is often used as a training ground for new principals. Yet little is known about how to design and implement on-the-job training opportunities that prepare assistant principals to serve as principals. During this webinar, KIPP—a charter management organization—discusses lessons learned from its experience preparing assistant principals as principals through job-embedded training. To accommodate its rapid growth in recent years, the KIPP charter network has developed strategies for developing assistant principals into instructional leaders. In the webinar, leaders from KIPP discuss: (1) on-the-job activities to develop the instructional leadership skills of assistant principals; (2) steps that principals can take to model instructional leadership and provide feedback to assistant principals; and (3) supports for principals who are developing the leadership skills of assistant principals.