Systematic interviews to technicians in charge of urban drainage were undertaken to assess the distribution of nature-based solutions (NBSs) for hydraulic risk mitigation in the Veneto region (Italy) and to investigate interventions that are priorities to address the challenges of urban growth and hydraulic risk. Specifically, this paper investigated stakeholders’ preference for green and gray infrastructure and for some NBSs in particular among those more frequently adopted, where they are predominantly implemented, and why. The results were interpreted in the context of significant geomorphological, socioeconomic, and regulatory parameters and how they relate to NBS implementation. The survey demonstrated that, among technical experts in one of Italy’s most developed regions, there may be a certain skepticism about the effectiveness of NBSs in counteracting the hydraulic risk of flooding, the close interrelation between political decisions in favour of NBS and the constrains of national and regional legislation, and the willingness to involve the population in the decision-making process. Further investigation showed that what (de)motivates the use of NBSs may be a partial disconnection between the academic, technical, and administrative sectors.