With the advancement of technologies related to ‘Internet of Things’, we are moving towards environments characterised by full integration and se-mantics. Various environments are often summarized with terms such as ‘Smart City’, ‘Smart Home’, ‘Smart Buildings’ or ‘Smart Commerce’. In the meantime, technologies and standards for interoperability have been developed. However, to realise the full potential one remaining challenge is the design, integration and interoperability of many elements into a smart environment. In order to address this challenge, researchers have proposed concepts for Information Systems De-sign and Enterprise Architectures. By inspecting interaction challenges -in par-ticular activities in which Humans are involved- during the design process, we endeavour in this paper to identify key challenges for designing smart environ-ments. In order to address the challenges we propose a conversational approach that supports the main design phases and allows professionals to interact during the design phases for smart environments.