The aim of this article is to examine design thinking from the perspective of social systems theory and interpret it as a way in which organizational systems may cope with the complexity of their social environment. The theoretical basis for this article is Niklas Luhmann’s theory of social systems (1995) and its more recent interpretations (Valentinov 2014a, 2014b) highlighting the precarious nature of the system-environment relationship. The specificity of complexity in user-centered design processes is characterized and design thinking methodology is analysed as providing means to meet the critical systemic requirements to reduce complexity but also remain sensitive to the critical aspects of environment. The theoretical argument is outlined and illustrated by the analysis of design thinking methodologies, frameworks and tools as presented in popular design thinking ‘guides’/’manuals’. The value of this article is that it emphasizes the role of systemic aspects of knowledge production and management within design processes. It allows to see design thinking processes as conditioned by the relationship between organizational system and its environment. The proposed interpretation may also be useful in terms of further development of design thinking methodologies and tools as well as adaptation of design thinking in areas lying outside traditional design.