This paper describes the process of a combined system dynamics modeling and scenario planning approach. It empirically investigates how envisioning and probing system dynamic modeling has the potential to raise effectiveness of scenario planning for organizational learning and improved decision making. The approach is illustrated by means of a case study that was used to explore the influence of social trends on dynamic interactions between transport behavior and spatial development in Switzerland. In this case study a system dynamics model was developed that served as a communication tool for strategy development and for enhancing goal alignment between different policy sectors at the national level. A qualitative content analysis illustrates how comments from participants of group modeling workshops can be opened up as empirical indicators of stimuli for improved learning. Additionally, it gives empirical evidence that the chosen approach contributes to mitigating four drivers of unexpected decision failure as discriminated by Chermack (2004a): bounded rationality, the tendency to consider only exogenous variables, stickiness and friction of information and knowledge, and mental model with decision premises.