Job interviews have been the object of extensive academic research and of advice literature. Yet both have largely neglected to incorporate findings drawn from naturally occurring job interviews. In this article, we focus on the case of giving negative remarks about third parties. Popular how-to books strongly advise against such comments; however, while analyzing our corpus of more than 20 naturally occurring Belgian employment interviews, the frequent use of negative remarks about third parties was striking. This discrepancy between actual practice and prescriptive literature inspired us to investigate this phenomenon by focusing on the interactional dynamics of one job interview in which a candidate comments negatively on his boss after having constructed a personalized identity of a trustworthy person. We argue that, in this particular case, this negative comment demonstrates the candidate’s adaptability to the discursively renegotiated “rules” of the “interview game” and that this can be a successful strategy in employment interviews. To conclude, in the light of these findings, we speculate on the utility of the advice that “how-to books” provide.