The concept of improvisation is discussed in management literature as a promising mechanism and design principle for an organization's capacity for learning, adaptability and innovation. However, a specific form of improvisation for coping with the duality of production and service has not yet been applied to the servitization of manufacturing or PSS. This paper introduces a specific form of semi-structured improvisational learning related to PSS-oriented organizations. It introduces an organizational design principle of desired and accepted improvisational actions for highly individualized customer solutions. This semi-structured form of improvisational learning separates PSS from manufacturing-oriented organizations, where improvisation is rather a phenomenon of resistive actions that trigger undesired deviations. By emphasizing the increasing importance of improvisation and improvisational learning as a desirable and acceptable principle of action, it is argued that this rather paradigmatic shift demands specific capabilities from individual actors in PSS. These individual capabilities are summarized in this paper as learning-oriented capabilities that unfold a dynamic balance of generative and adaptive learning activities in PSS. As this specific pattern of individual capabilities is less cultivated in pure manufacturing, a game-based training and learning approach is introduced which is designed to accompany individual actors during the servitization process. The game-based learning scenario focuses on the development of individual improvisational capabilities as a mediating force in the dynamic triangle of customer, production and service. In conclusion, the literature review of this paper contributes to the scientific community by framing the servitization of manufacturing with the concept of improvisation as a coping strategy for the dynamics and ambiguity in PSS. Furthermore, a training and development approach is specified that aims at equipping individual actors with capabilities of improvisation and improvisational learning as prerequisites for the operation of highly individualized PSS. This training approach is also intended to be applicable for practitioners.