As markets are getting more dynamic and complex, there is the need to focus on alignment and adaptability simultaneously within an entire business unit, either on an individual or team level. Besides that, to respond quickly to changes on the market and specific requirements, the implementation of a more flexible organization form is vital to stay competitive and survive on the volatile external market. This can be reached by implementing self-organizing teams that are empowered and handling customer projects on their own. This thesis has the aim to identify important influencing factors and the organizational context factors for the development and collaboration of contextual ambidextrous self-organizing teams. Besides that, important HR practices and the role of the top management within such flexible organizations are found and discussed. In this thesis, the results were obtained by conducting qualitative interviews within a medium-sized organization, which is operating within the industry of multimedia and internet. The interviews were conducted within this organization, as they changed their structures from a classic top-down hierarchy to two self-managing teams that are handling the customer projects on their own in small project teams. The findings show that important influencing factors for the successful collaboration and development of contextual ambidextrous self-organizing teams are the following ones: organizational factors (structure and culture), team factors, individual factors, external factors and human resource practices. Additionally, the role of the top management is on the one hand to ensure efficiency by handling performance management, giving the overall strategic direction and making clear boundaries for decision-making. On the other hand, the management has to support the project teams whenever they need help and building trust to them, to foster flexibility and creativity. Are these influencing factors there within an organization, then contextual ambidextrous self-organizing teams can high perform and contribute to the success of the whole organization.