What Types of Questions Require Conversation to Answer? A Case Study of AskReddit Questions

The proliferation of automated conversational systems such as chatbots, spoken-dialogue systems, and smart speakers, has significantly impacted modern digital life. However, these systems are primarily designed to provide answers to well-defined questions rather than to support users in exploring complex, ill-defined questions. In this paper, we aim to push the boundaries of conversational systems by examining the types of nebulous, open-ended questions that can best be answered through conversation. We first sampled 500 questions from one million open-ended requests posted on AskReddit, and then recruited online crowd workers to answer eight inquiries about these questions. We also performed open coding to categorize the questions into 27 different domains. We found that the issues people believe require conversation to resolve satisfactorily are highly social and personal. Our work provides insights into how future research could be geared to align with users' needs.