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The effectiveness of clarification question models in engaging users within search systems is currently constrained, casting doubt on their overall usefulness. To improve the performance of these models, it is crucial to employ assessment approaches that encompass both real-time feedback from users (online evaluation) and the characteristics of clarification questions evaluated through human assessment (offline evaluation). However, the relationship between online and offline evaluations has been debated in information retrieval. This study aims to investigate how this discordance holds in search clarification. We use user engagement as ground truth and employ several offline labels to investigate to what extent the offline ranked lists of clarification resemble the ideal ranked lists based on online user engagement. Contrary to the current understanding that offline evaluations fall short of supporting online evaluations, we indicate that when identifying the most engaging clarification questions from the user’s perspective, online and offline evaluations correspond with each other. We show that the query length does not influence the relationship between online and offline evaluations, and reducing uncertainty in online evaluation strengthens this relationship. We illustrate that an engaging clarification needs to excel from multiple perspectives, and SERP quality and characteristics of the clarification are equally important. We also investigate if human labels can enhance the performance of Large Language Models (LLMs) and Learning-to-Rank (LTR) models in identifying the most engaging clarification questions from the user’s perspective by incorporating offline evaluations as input features. Our results indicate that LTR models do not perform better than individual offline labels. However, GPT, an LLM, emerges as the standout performer, surpassing all LTR models and offline labels. 

Conversational information seeking (CIS) is concerned with a sequence of interactions between one or more users and an information system. Interactions in CIS are primarily based on natural language dialogue, while they may include other types of interactions, such as click, touch, and body gestures. This monograph provides a thorough overview of CIS definitions, applications, interactions, interfaces, design, implementation, and evaluation. This monograph views CIS applications as including conversational search, conversational question answering, and conversational recommendation. Our aim is to provide an overview of past research related to CIS, introduce the current state-of-the-art in CIS, highlight the challenges still being faced in the community, and suggest future directions. 

Understanding and characterizing how people interact in information-seeking conversations will be a crucial component in developing effective conversational search systems. In this paper, we introduce a new dataset designed for this purpose and use it to analyze information-seeking conversations by user intent distribution, co-occurrence, and flow patterns. The MSDialog dataset is a labeled conversation dataset of question answering (QA) interactions between information seekers and providers from an online forum on Microsoft products. The dataset contains more than 2,000 multi-turn QA dialogs with 10,000 utterances that are annotated with user intents on the utterance level. Annotations were done using crowdsourcing. With MSDialog, we find some highly recurring patterns in user intent during an information-seeking process. They could be useful for designing conversational search systems. We will make our dataset freely available to encourage exploration of information-seeking conversation models.