In a digitally empowered business world, a growing number of family businesses are leveraging the use of chatbots in an attempt to improve customer experience. This research investigates the antecedents of chatbots’ successful use in small family businesses. Subsequently, we determine the effect of two distinctive sets of human–machine communication factors—functional and humanoid—on customer experience. We assess the latter with respect to its effect on customer satisfaction. While a form of intimate attachment can occur between customers and small businesses, affective commitment is prevalent in customers’ attitudes and could be conflicting with the distant and impersonal nature of chatbot services. Therefore, we also test the moderating role of customers’ affective commitment in the relationship between customer experience and customer satisfaction. Data come from 408 respondents, and the results offer an explicit course of action for family businesses to effectively embed chatbot services in their customer communication. The study provides practical and theoretical insights that stipulate the dimensions of chatbots’ effective use in the context of small family businesses.