Efficiently exploiting existing business while simultaneously exploring new opportunities can generate tensions for actors who find themselves at the crossroads. It is the case of exploration entities’ managers, who have to pursue a long term exploration mission, while being often evaluated through short term exploitation-oriented corporate governance rules. Based on four longitudinal studies of exploration entities, we shed light on the middle management practices and roles undertook by the entities’ managers in order to overcome this tension: promotion, conformism, transformation, decoupling. Our results illustrate how these roles are linked to the dynamic of the exploration entities over time, and how they facilitate or refrain the organizational ambidexterity.