In the context of information seeking, conversational agents are undergoing an evolution from reactive tools to proactive, personalized assistants. A critical aspect of this evolution is the ability to tailor strategic interactions to a user's unique needs and expectations. Unlike existing studies that focus on proactively clarifying query ambiguities, we center on clarifying the user's expertise in order to tailor responses for better user comprehension. We find that existing agents struggle to determine user expertise from queries alone, a limitation that prevents them from dynamically adapting their responses. To address this gap, we introduce PASSING to empower the agent to proactively clarify a user's expertise through targeted inquiries. This is achieved by our What-to-ask and How-to-ask strategies, induced by LLM self-play. Our extensive experiments also show our superiority. We believe that PASSING represents a crucial step towards creating more human-centric conversational agents.

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