If professional learning leaders are looking for a clear path lined with models of best program evaluation practices, they will become tangled in the weeds. After working for several decades to help professional learning leaders and their teams improve programs and evaluations, the author has observed several habits of mind and work that can make a significant difference in the quality of evaluations. Based on the author's observations, this article describes 10 stepping stones for leaders growing curious or anxious about undertaking solid evaluation practices.