Currently, conversations with chatbots are perceived as unnatural and impersonal. One way to enhance the feeling of humanlike responses is by implementing an engaging communication style (i.e., Conversational Human Voice (CHV); Kelleher, 2009) which positively affects people’s percep-tions of the organization. This communication style contributes to the effectiveness of online communication between organizations and customers (i.e., webcare), and is of high relevance to chatbot design and development. This project aimed to investigate how insights on the use of CHV in organizations’ messages and the perceptions of CHV can be implemented in customer service automation. A corpus study was conducted to investigate which linguistic elements are used in organizations’ messages. Subsequently, an experiment was conducted to assess to what extent linguistic ele-ments contribute to the perception of CHV. Based on these two studies, we investigated whether the amount of CHV can be identified automatically. These findings could be used to design humanlike chatbots that use a natural and personal communication style like their human conversation partner.