This chapter focuses on the Singaporean negotiation style and the practical approaches one could take when negotiating in the Singapore context. The Singaporean negotiator’s mindset, whilst individual, remains embedded in and shaped by the discourse contexts of the Singapore government (‘The Singapore Way’), and Singapore’s business environment, which is shaped by forces of regionalization and globalization. Singapore’s multiracial, multilingual background provides a unique business environment that, together with its geolocation, places the country at the heart of an increasingly interconnected Asia and Southeast Asia. The central theory espoused in this study is based in functional grammar that views language as a social semiotic—a tool for semogenesis or meaning-making. Language is an inherent feature of the human faculty, where most social functions are communicated and acted upon through language-in-use, across various forms of negotiations. Semogenesis and the communication of meaning are central to successful negotiations. Taking as case examples respondents from the Singapore business community as well as prominent individuals serving in the Singapore government, this study uses language as a theory and a framework of meaning-making to uncover the mindset of the Singapore negotiator, studied in relation to the supporting contexts of the Singapore business environment. Rather than a normative, static-cultural-dimensions construct approach which tends to perpetuate cultural stereotypes, this study illustrates how the complexity of interaction in the Singapore business environment generates a Singaporean approach to negotiation that is highly nuanced in nature.