The paper focuses on investigating some of the challenges of teaching interaction design. This analysis is based on two pillars: a series of learning theories that can be used to inform the paper topic and a set of interviews with design practitioners who were previously enrolled in a third level education program aimed to prepare them for this profession. The findings suggest that both teaching and practicing design require good coaching, practical experience together with a thorough understanding that can occur through reflecting on experience, and not at least access to community of practice that can enable successful communication, both with the coacher and the peers.