In this insightful article, Richard Busby, M.S., explores the valuable lessons learned from assisting a struggling student and the broader implications for learning leaders. Through a compelling narrative, Busby emphasizes the importance of understanding learners' struggles, engaging in meaningful dialogue to identify specific obstacles, and developing targeted solutions. He introduces key themes: the necessity of learners articulating their challenges, the critical role of leaders in facilitating these discussions, and the risk of implementing poor solutions without precise problem identification. Busby also delves into the complexities of instructional systems, the significance of content complexity and pace of change, and the need for adaptive learning systems that accommodate diverse learners. By asking fundamental questions and challenging established paradigms, this article provides a comprehensive framework for enhancing educational outcomes and preparing students for future success.