There are inherently authoritarian and hierarchical assumptions, expectations, and processes of education embedded within our learning institutions which complicate and often confound educators' efforts to create collaborative environments for learning. Education leaders face the well-known challenge of adhering to mandated curricula and assessments while adapting to ever-changing best practices. This chapter explores the transformative potential of integrating improvisation and theatre games into educator, administrator, and school leadership training. The authors present a perspective of improvisation as an often-overlooked philosophy and practice for educators with the capacity to reconnect them with foundational values for education and learning rooted in building relationships through co-creational problem-solving and play. Drawing upon the work of Viola Spolin, this chapter presents an overview of improvisation as a philosophy and practice with direct connection and implications for realizing essential educational theories that have come to define the P-20 landscape.