Small and Medium-sized Enterprises (SMEs) are being faced with rapid changes in their business environments due to evolution of technologies and innovation in societal eco-systems. Particularly, dynamic interactions between such environments and enterprise activities have become significant, so technology planning, which is a process of identifying appropriate directions regarding product and technology development, has received much attention to cope with such dynamics proactively. However, SMEs typically have limits in performing independent, strategical and systematical technology planning activities due to the lack of human, material and financial resources. This paper proposes the development of a product roadmapping method so that SMEs carry out efficient technology planning activities with interconnections of external business environments. The present work provides product roadmap templates that directly accommodate the influence of business environments on the product’s system and its associated super/sub-systems with the use of external environment analysis techniques including TRIZ methodology, PEST and 5Forces analysis. These templates are useful to efficiently forecast the directions of product’s development and evolution, which arise from changes in external environments. Consequently, the present work enables SMEs to flexibly cope with the era of the next R&D generation, which pursues value creation through mutual interconnection between business environments and technology development.