Though they can be traced back to different roots, both smart design and smart systems have to do with the recent developments of artificial intelligence. There are two major questions related to them: (i) What way are smart design and smart systems enabled by artificial narrow, general, or super intelligence? and (ii) How can smart design be used in the realization of smart systems? and How can smart systems contribute to smart designing? A difficulty is that there are no exact definitions for these novel concepts in the literature. The endeavor to analyze the current situation and to answer the above questions stimulated an exploratory research whose first findings are summarized in this paper. Its first part elaborates on a plausible interpretation of the concept of smartness and provides an overview of the characteristics of smart design as a creative problem solving methodology supported by artificial intelligence. The second part exposes the paradigmatic features and system engineering issues of smart systems, which are equipped with application-specific synthetic system knowledge and reasoning mechanisms. The third part presents and elaborates on a conceptual model of AI-based couplings of smart design and smart systems. The couplings may manifest in various concrete forms in real life that are referred to as “connectors” in this paper. The principal types of connectors are exemplified and discussed. It has been found that smart design tends to manifest as a methodology of blue-printing smart systems and that smart systems will be intellectualized the enablers of implementation of smart design. Understanding the affordances of and creating proper connectors between smart design and smart systems need further explorative research.