ABSTRACT This paper uses grounded practical theory (GPT) to examine how members of a pan-Asian organization manage dilemmas surrounding race and the workplace. An action implicative discourse analysis of 20 hours of audio-recorded meeting interactions among members of an Asian American Chamber of Commerce (AACC) reveals two dilemmas: how to maintain solidarity among an ethnically diverse group and how to communicate a racialized business identity to external corporate donors. Participants managed dialectical tensions between similarities and difference through membership categorization, metadiscourse, humor, and code-switching. Analysis illustrates that AACC practices operate from a locus of difference that values ‘diversity’ as a shared identity and provides leeway for creatively constructing difference. This paper extends GPT as a framework that highlights race as central to communication problems in the workplace and discusses how a better understanding of complexities of Asian American identity negotiation can offer practical insights into present-day race relations and diversity initiatives.