Niche markets are essential for commercialization of radical new innovations. In a niche market, the innovation is protected while gaining maturity till finally being able to compete with the incumbent technology in the mass market. Along the way towards large-scale diffusion, firms can apply niche strategies as a deliberate and temporary choice to cope with internal and/or external factors that have become barriers hampering diffusion. Although it seems clear that certain barriers can be overcome by certain niche strategies, a clear means of assessing technology diffusion in view of those factors such to be able to identify circumstances that allow/require to adopt another niche strategy to continue to diffuse, remains underexplored. Accordingly, this research defines a set of indicators to assess contextual and contemporary factors potentially hampering diffusion of a radical innovation throughout the diffusion period. This set of indicators can then function as a trigger for commercial firms to rationally revisit their niche strategies according to the ever-changing internal/external environment during the often erratic path of technology diffusion, such to pursue large-scale diffusion. A case study will be conducted by analysing two urban farming organizations in the Netherlands, with urban farming being a yet-to-diffuse radical innovation aiming for fresh and sustainable food supply in urban areas. A non-static conceptual model and method of use are constituted that includes factors, indicators and triggers to rationally assess the business environment on diffusion hampering factors/barriers, and to select niche strategies accordingly.