Purpose: This paper aims to provide an overview of the Organization Learning and Learning Organization concepts obtaining the perspectives of Professor Mary M. Crossan and presents an evolution of her immense contribution to the field over the past two decades. Design/methodology/approach: A conversation with thought-leader, Professor Mary M. Crossan. Findings: How different "character configurations" and "processes" enhance organization learning across levels in the organization. Originality/value: The discussion with Professor Mary M. Crossan reveals her take on the evolution of the organizational learning framework and the significant role of the "Leader's Character" in shaping organizational learning. Exploring this evolution provides the context and impetus to researchers and practice leaders to verify.