This thesis presents my responses to questions posed by four professors with whom I studied while completing my coursework in the Organizational Master’s Degree program at the University of Pennsylvania. My paper will present various perspectives on learning organizations – organizations characterized by a capability to adapt to changes in environment. All questions posed by each professor impact learning organizations in some manner. Dr. Stankard’s questions focus on the roadblocks organizations face when transforming to learning organizations. Dr. Kaminstein’s questions center on how organizations can become less individualistic and more team-centered. Dr. Wilkinsky queried how developmental coaching might be used to increase organizational performance. Finally, Dr. Russo asked how to address the misalignment that occurs when the leader-manager’s coaching model is not the same as the larger organization. This project has allowed me to investigate and reflect on potential key drivers of organizational learning. I have learned that a multitude of individual and organizational complexities – internal and external – affect and determine if organizations learn and whether learning is sustained. To successfully navigate those complexities through planned interventions is a core tenet of organizational development and the hallmark of a true learning organization.