This chapter discusses the problematic assessment of integrated transport plans in a Cost-Benefit Analysis (CBA), resulting in many process-related issues: the use of the CBA as a final assessment and communication deficits and distrust between plan owners and evaluators. It then explores two research studies that aimed to tackle this issue. First, a CBA Dialogue was constructed based on insights from communicative planning and organizational learning literature with five interventions that might trigger the necessary mechanisms for comprehensive communication. Second, this CBA Dialogue was applied in an experiential case study in two sequential cases to better understand if and how it might improve communication and trust between plan owners and evaluators. The experiential case study, with two sequential cases, was necessary for this transition and narrowed the gap between theory and practice, improving the application of theoretical interventions in practice by making them more context-specific.