This paper focuses on the pedagogical challenges that stem from teaching students how to overcome cultural hurdles when interpreting between Mandarin Chinese and English in a conference setting. Training interpreters to work between Chinese and English is especially challenging because the two languages are very different in social and cultural backdrops. Apart from linguistic competence, interpreting trainees must also work on cultural literacy and acquire strategic competence in order to become competent conference interpreters. In this paper, I first attempt to identify the major problems that trainees of conference interpreting have to be alerted to as they assume the roles of intercultural communicators. Then I stress the importance of teaching intercultural awareness and cultural literacy, using Edward Hall’s classification of cultures as a working model. Finally, I give suggestions on how to teach strategic competence in order to help students overcome culture bumps.