Complex domains demand task-oriented dialog system (TODS) to be able to reason and engage with humans in dialog and in information retrieval. This may require contemporary dialog systems to have improved conversation handling capabilities. One stating point is supporting conversations which logically advances, such that they could be able to handle sub dialogs meant to elicit more information, within a topic. This paper presents some findings on the research that has been carried out by the authors with regard to highlighting this problem and suggesting a possible solution. A solution which intended to minimize heavy reliance on handcrafts which have varying challenges. The study discusses an experiment for evaluating a novel architecture envisioned to improve this conversational requirement. The experiment results clearly depict the extent to which we have achieved this desired progression, the underlying effects to users and the potential implications to application. The study recommends combining Agency and Reinforcement learning to deliver the solution and could guide future studies towards achieving even more natural conversations.