Elicited conversations with participants engaged in a problematic negotiation with their boss were analyzed in groups of native speakers of British English, Chilean Spanish and Swedish, and in groups of Swedish speakers of L2 English and L2 Spanish (longtime residents in their host community and highly proficient in their L2). Two planes of comparison were involved: cross-culturally, addressing differences between the native groups, and, inter-culturally, addressing interaction between natives and non-natives. Results show considerable distance between the three L1 groups, especially regarding how power distance and social distance are managed both by the ‘employees’ and the ‘bosses’. As regards L2 speaker behavior, alignment with target community patterns largely prevails and few instances of L1 transfer occur. Communicative clashes are found to take place more often in the Swedish-Spanish encounters than in the Swedish-English ones, arguably due to the wider cultural distance between the Chilean and Swedish socio-cultures.