Developing dialogue systems capable of engaging in multi-turn, goal-oriented conversations remains a significant challenge, especially in specialized domains with limited data. This research proposes a novel framework called Preference Tree Optimization (PTO), designed to iteratively improve agent models in such dialogue systems, by generating preference data using a method called Preference Tree with Look-Ahead. Focusing on Motivational Interviewing (MI) -- a counseling technique aimed at facilitating behavioral change -- we leverage virtual patients and an oracle evaluator to simulate conversations and generate rich preference datasets. By combining this method with Direct Preference Optimization (DPO), we aim to enhance the agent's decision-making capabilities over iterative training cycles. The proposed framework addresses data scarcity and advances the development of more nuanced and effective dialogue systems in goal-oriented domains. Experimental evaluations demonstrate that the PTO framework enhances dialogue agents' performance in goal-oriented conversations within the domain of Motivational Interviewing (MI). Models trained with PTO consistently outperformed the baseline in key metrics such as session satisfaction and working alliance. Additionally, incorporating look-ahead simulations led to improved long-term planning and more effective conversational strategies, with deeper look-ahead configurations yielding the most stable and high-scoring results.
Existing machine translation (MT) metrics and discourse-focused evaluations primarily assess translation quality intrinsically, without measuring the downstream consequences of translation errors. In this work, we focus on extrinsic discourse evaluation of machine translation under two distinct regimes: static and interactive. Under the static regime, we propose an entity counting task as a probe of referential consistency in discourse. We show that high intrinsic MT quality does not reliably predict downstream discourse success and strong MT systems still produce referential inconsistencies. For the interactive regime, we study the goal-oriented multi-agent Welfare Diplomacy game as a probe of long-horizon communication and coordination. We find that interaction-specific translation failures impact downstream coordination. Our results highlight goal-oriented environments as a viable framework for discourse-sensitive extrinsic MT evaluation.