Background: Many powered wheelchair users find their medical condition and their ability to drive the wheelchair will change over time. In order to maintain their independent mobility, the powered chair will require adjustment over time to suit the user's needs, thus regular input from healthcare professionals is required. These limited resources can result in the user having to wait weeks for appointments, resulting in the user losing independent mobility, consequently affecting their quality of life and that of their family and carers. In order to provide an adaptive assistive driving system, a range of features need to be identified which are suitable for initial system setup and can automatically provide data for re-calibration over the long term. Methods: A questionnaire was designed to collect information from powered wheelchair users with regard to their symptoms and how they changed over time. Another group of volunteer participants were asked to drive a test platform and complete a course which represented manoeuvring in a very confined space as quickly as possible. Two of those participants were also monitored over a longer period in their normal home daily environment. Features, thought to be suitable, were examined using pattern recognition classifiers to determine their suitability for identifying the changing user input over time. Results: The results are not designed to provide absolute insight into the individual user behaviour, as no ground truth of their ability has been determined, they do nevertheless demonstrate the utility of the measured features to provide evidence of the users’ changing ability over time whilst driving a powered wheelchair. Conclusions: Determining the driving features and adjustable elements provides the initial step towards developing an adaptable assistive technology for the user when the ground truths of the individual and their machine have been learned by a smart pattern recognition system.