A gap often exists between adult leadership learning and development practice. This gap seems particularly pronounced when considering training through a collective, practice, and constructionist theoretical lens. Leadership developers need to address this gap in their teaching methods if they are to support learning capable of responding to Complex Adaptive System (CAS) challenges. Drawing from a case-in-point (CIP) train-the-trainer experience hosted by the Kansas Leadership Center (KLC) this study will help trainers understand how primary and keying frames can be used to analyze how facilitators train trainers to use collective sensemaking for adult leadership learning. The case-in-point leadership development method is capable of moving adult leadership learners to make more systemic interpretations of leadership challenges and collectively interrogate cultural assumptions and identity.