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Although the organizational context has been identified as an important factor contributing to the success or failure of leadership training initiatives, exploration of the interaction between differing contextual perceptions in relation to the transfer of leadership training is lacking. Building on Oc’s framework on context and leadership, we examine how the degree of perceptual alignment of leader and teams on two contextual factors, formalization and employee orientation, were related to followers’ ratings of transformational leadership after a leadership training in the forest industry (n = 37 leaders). Polynomial regression with response surface analysis revealed that agreement between leaders and their teams on formalization and employee orientation predicted improvements in transformational leadership but only up to a certain point. At high levels of formalization agreement negatively impacted leaders’ development of transformational leadership, and at high levels of employee orientation the positive impact of agreement flattened out. Leaders who rated formalization and employee orientation higher than their teams increased their transformational leadership to a lesser extent as rated by their followers. Our findings extend the framework developed by Oc and offer a new perspective on the complex interplay between leader, follower, and contextual factors that all matter for successful leadership training transfer.