In this paper, we introduce a novel framework SimSeek (simulating information-seeking conversation from unlabeled documents) and compare two variants of it to provide a deeper perspective into the information-seeking behavior. We first introduce a strong simulator for information-symmetric conversation, SimSeek-sym, where questioner and answerer share all knowledge when conversing with one another. Although it simulates reasonable conversations, we take a further step toward more realistic information-seeking conversation. Hence, we propose SimSeekasym that assumes information asymmetry between two agents, which encourages the questioner to seek new information from an inaccessible document. In our experiments, we demonstrate that SimSeek-asym successfully generates information-seeking conversations for two downstream tasks, CQA and conversational search. In particular, SimSeek-asym improves baseline models by 1.1-1.9 F1 score in QuAC , and by 1.1 of MRR in OR-QuAC (Qu et al., 2020). Moreover, we thoroughly analyze our synthetic datasets to identify crucial factors for realistic information-seeking conversation.