This article explores paradoxes that emerge in the mentoring of highly-educated, female, foreign-born job-seekers in Finland. Theoretically, the study is linked to the growing body of research scrutinising the integration or discrimination of migrants in working life. It analyses cultural practices and ideas that are visible and affect the mentoring interaction. On a more practical level, the paper determines how the mentors and mentees experience the mentoring, and how intercultural mentoring could be improved in order to promote mentees’ employment. The article is based on ethnography and 11 semi-structured interviews. Two major paradoxes and their links to cultural meanings were identified: the over-emphasised focus on Finnish language (the language paradox), and the myth of the strong Finnish woman (the support paradox). These can be seen as having aspects of both cultural awareness and situation-specific awareness. Using situation-specific awareness, some mentors understood the best way forward was to break the rules of the mentoring programme and not to use Finnish in all communication. This enabled a more equal setting for professional discussions. In some rare cases, when the mentors did not use situation-specific awareness, a vicious circle emerged and mentees felt even worse about their abilities and working life opportunities. Similarly, although the myth of the strong Finnish woman can be an empowering and positive model for the mentee, it can have a negative impact on the mentor, enabling undercurrents in the mentoring discussions which can be experienced as harsh and even hostile. This, instead of encouraging and supporting, can result in the undermining and ‘othering’ of the mentee.