Career interest assessment is a vital component of career guidance and counseling. Ensuring fair and ethical assessment practice is, however, complex and challenging in a diverse multicultural setting such as South Africa. A myriad of factors—including culture, and language—may moderate individual performance on career interest assessments. For this reason, it is imperative to acknowledge these factors when developing career interest assessments in the South African context. Particular attention was paid to the issues of language and culture during the recent development of the South African Career Interest Inventory (SACII) and South African Career Interest Inventory-isiXhosa version (SACII-X). In this paper, we discuss some of the crucial considerations that informed the conceptualization and development of the SACII-X. The promising initial reliability and validity demonstrated by these assessments provide support for the use of career assessments based on imported career theories if sensitivity is afforded to contextual, language, and cultural considerations during the development of such assessment measures.