Qualitative research studies often employ a contextual inquiry, or a field study that involves in-depth observation and interviews of a small sample of study participants, in-situ, to gain a robust understanding of the reasons and circumstances that led to the participant's thoughts, actions, and experiences regarding the domain of interest. Contextual inquiry, especially in sensitive data studies, can be a challenging task due to reasons such as participant privacy, as well as physical constraints such as in-person presence and manual analysis of the qualitative data gathered. In this work, we discuss Enqu\^ete Contextuelle Habile Ordinateur (ECHO); a virtual-assistant framework to automate the erstwhile manual process of conducting contextual inquiries and analysing the respondents' subjective qualitative data. ECHO automates the contextual inquiry pipeline, while not compromising on privacy preservation or response integrity. Its adaptive conversational interface enables respondents to provide unstructured or semi-structured responses in free-form natural language, allowing researchers to explore larger narratives in participant response data. It supports response-driven exploratory questions and automates coding methodologies for qualitative data, thus enabling the inquirer to dive deeper into correlated questions and to do better cause-effect analysis. It focuses on addressing the limitations of manual annotation, bringing standardisation to free-form text, and eliminating perspective bias amongst different reviewers of subjective responses. A participatory mental health study was conducted on 167 young adults bifurcated into two focus groups; one of which was administered a conventional contextual inquiry, and the other via ECHO, virtually. ECHO outperformed on participant transparency, response detail and median time required for end-to-end inquiry completion, per participant.
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