Brainteaser interview questions such as “Estimate how many windows are in New York” are just one example of aggressive interviewer behaviour that lacks evidence for validity and is unsettling to job applicants. This research attempts to shed light on the motives behind such behaviour by examining the relation between dark‐side traits and the perceived appropriateness of brainteaser interview questions. A representative sample of working adults (n = 736) was presented with a list of interview questions that were either traditional (e.g., “Are you a good listener?”), behavioural (e.g., “Tell me about a time when you failed”), or brainteaser in nature. Results of a multiple regression, controlling for interviewing experience and sex, showed that narcissism and sadism explained the likelihood of using brainteasers in an interview. A subsequent bifactor analysis showed that these dark traits shared a callousness general factor. A second longitudinal study of employed adults with hiring experience demonstrated that perspective‐taking partially mediated the relationship between this general factor and the perceived helpfulness and abusiveness of brainteaser interview questions. These results suggest that a callous indifference and a lack of perspective‐taking may underlie abusive behaviour in the employment interview.