Design-build contractors are challenged with the task of minimizing failure risks when introducing new technical solutions or adapting technical solutions to new conditions, e.g., climate change. They seem to have a disproportional trust in suppliers and their reference cases and might not have adequate resources or methodologies for sufficient evaluation. This creates the potential for serial failures to spread in the construction industry. To mitigate this, it was suggested that a predefined risk assessment framework should be introduced with the aim of providing a prequalification and requirements for the use of the technical solution. The objectives of this paper are to develop a comprehensive risk assessment framework and to explore the framework’s potential to adequately support the design-build contractor’s decisions. The framework uses qualitative assessment, relying on expert workshops and quantitative assessments, with a focus on simulation and probabilities. Tollgates are used to communicate risk assessments to the contractor. The framework is applied to a real-life case study of construction with a CLT-structure for a Swedish design-build contractor, where exposure to precipitation during construction is a key issue. In conclusion, the chosen framework was successful in a design-build contractor context, structuring the process and identifying difficulties in achieving the functional requirements concerning moisture. Three success factors were: documentation and communication, expert involvement, and the use of tollgates. Recommendations to the design-build contractor on construction of CLT structure are to keep construction period short and to use full weather protection on site.