In recent years, there has been an increasing focus on professional learning structures for teaching and finding ways to embed this learning into the daily work of teachers. This is premised on the understanding that one-shot professional development yields little transfer or change of practice to ultimately impact student learning. But how has this shift from professional development to professional learning filtered into the world of school leadership? The author contends that the reach has been limited and that when districts are juggling limited resources, they rarely prioritize the professional learning needs of school-based administrators (principals and assistant principals). In this article, the author reflects on two years spent at the Utah Salt Lake City School District office as a principal supervisor. This article examines some of the author's learnings about ways to support principals as learners.