Working environments are becoming more and more automated. Therefore, operators must be able to monitor the automated processes accurately and efficiently. Since the German Aerospace Centre’s Department of Aviation and Space Psychology is responsible for selecting pilots and air traffic control personnel, our objective for future selections is to distinguish between operators monitoring well and those monitoring poorly. By identifying accurate monitoring behaviour we are able to adapt selection profiles to future ability requirements. In order to identify good monitoring behaviour, we developed a tool which simulates the tasks of pilots and controllers within a dynamic air traffic flow. Participants either have to monitor the automatic process or manually control the dynamic traffic. Monitoring behaviour is measured by recording eye movement parameters and performance during the manual control phase is assessed. Additionally, the effect of complacency potential as a moderator of both monitoring behaviour and manual controlling behaviour was examined. Although technology-related complacency was found to have no effect, tolerance of ambiguity indeed were found to have an effect on manual controlling behaviour. Additionally the subjects’ conscientiousness moderated the effect of monitoring behaviour on manual controlling behaviour.