In this paper, we introduce a novel framework, SIMSEEK, (Simulating information-Seeking conversation from unlabeled documents), and compare its two variants. In our baseline SIMSEEK-SYM, a questioner generates follow-up questions upon the predetermined answer by an answerer. On the contrary, SIMSEEK-ASYM first generates the question and then finds its corresponding answer under the conversational context. Our experiments show that they can synthesize effective training resources for CQA and conversational search tasks. As a result, conversations from SIMSEEK-ASYM not only make more improvements in our experiments but also are favorably reviewed in a human evaluation. We finally release a large-scale resource of synthetic conversations, WIKI-SIMSEEK, containing 2 million CQA pairs built upon Wikipedia documents. With the dataset, our CQA model achieves state-of-the-art performance on a recent CQA benchmark, QuAC.