Artificial Intelligence (AI) has the capabilities of performing tasks such as visual perception, speech recognition, decision-making and language translations, among others. Where AI has become especially pivotal for users’ interactions is in the case of voice-based assistants (VAs). VAs have developed considerably in recent years and their functionality goes way beyond initial perceptions. Some reports go as far to discuss how Amazon has plans to be able to run someone’s entire life from the Alexa on the basis that the systems are getting so sophisticated and the data being collected is so vast that the Alexa will be capable of predicting needs. Despite the benefits and opportunities of AI software, it is inherently limited by capabilities surrounding planning, reasoning, knowledge, natural language processing, ability to move and to empathise. It is this lack of emotional connection that is a fundamental component of users being less trusting towards AI voice-based assistants. This paper discusses the emerging capabilities of VAs whilst acknowledging the roles of trust and privacy concerns and proposes a mixed-method methodology approach, comprising of qualitative interviews and experimental design. Results of the qualitative data collection are reported and discussed and provides direction for the experimental design.