Hong Kong society has put family-friendly workplace policies under serious discussion, but the investigation of the views of employers remains insufficient. Adopting the structure-agency paradigm, this study used survey data to examine how structural constraints in business and the subjective world of individual employers influence their support to paid family leave. We found that industry categories were significantly associated with employers’ support but not the size of their enterprises. Employers’ personal stereotypes of family caregivers and their awareness of relevant laws did not exert significant independent effects on their policy support, but the significant interaction of the two suggested that employers with knowledge of regulations were less likely to formulate attitudes towards paid family leave based on their own stereotypes. Policy practices therefore need to consider the rationality of employers in the local contexts of Hong Kong, and aim to integrate legal education with de-stigmatisation of family caregivers in advocacy programs.