Virtual reality (VR) has been widely investigated for measuring and enhancing human physical performance. However, the assessment of human cognitive performance still relies on traditional pen-and-paper tests which are time-consuming, costly, and prone to biased results. We present an exploratory study investigating possible VR approaches to efficiently and reliably measure the cognitive performance of older adults in residential care facilities. Based on a review of established analog tests for assessing cognitive capabilities, three VR experts conceived related concepts for VR applications. In subsequent expert interviews, five neuropsychologists and care specialists validated concepts and provided additional insights into general requirements as well as possible success factors and barriers of VR-based assessment of cognitive capabilities. Although we found that direct transfer of established analog tests to VR is difficult and not effective, simulation of everyday situations proved to be promising. Specifically, assessments targeting orientation and navigation in everyday contexts could be enhanced through VR applications.