Planning a trip on public transport is an important step that can be time-consuming and nerve-wracking. Finding the right connection is not always simple, especially since personal preferences influence the selection of the most suitable route. Finding the most suitable route passenger's mobility preferences need to be known by the journey planning system. However, collecting these individually mobility preferences is a time-consuming process. Our contribution applies the contextual inquiring method determining what mobility preferences are most important. Based on these findings, we introduce a prototyping approach automatically determining four of the most important mobility preferences. The detected parameters are used to enrich user's future trip requests, assisting passengers to have pleasant and stress-free journeys from door to door.