arXiv:2605.14057v1 Announce Type: new Abstract: Most existing dialogue systems are user-driven, primarily designed to fulfill user requests. However, in many critical real-world scenarios, a conversational agent must proactively extract information to achieve its own objectives rather than merely respond. To address this gap, we introduce \emph{Inquisitive Conversational Agents (ICAs)} and develop an ICA specifically tailored to U.S. Supreme Court oral arguments. We propose a Dual Hierarchical Reinforcement Learning framework featuring two cooperating RL agents, each with its own policy, to coordinate strategic dialogue management and fine-grained utterance generation. By learning when and how to ask probing questions, the agent emulates judicial questioning patterns and systematically uncovers crucial information to fulfill its legal objectives. Evaluations on a U.S. Supreme Court dataset show that our method outperforms various baselines across multiple metrics. It represents an important first step toward broader high-stakes, domain-specific applications.