Designing dialog tutors has been challenging as it involves modeling the diverse and complex pedagogical strategies employed by human tutors. Although there have been significant recent advances in neural conversational systems using large language models and growth in available dialog corpora, dialog tutoring has largely remained unaffected by these advances. In this paper, we rigorously analyze various generative language models on two dialog tutoring datasets for language learning using automatic and human evaluations to understand the new opportunities brought by these advances as well as the challenges we must overcome to build models that would be usable in real educational settings.We find that although current approaches can model tutoring in constrained learning scenarios when the number of concepts to be taught and possible teacher strategies are small, they perform poorly in less constrained scenarios.Our human quality evaluation shows that both models and ground-truth annotations exhibit low performance in terms of equitable tutoring, which measures learning opportunities for students and how engaging the dialog is.To understand the behavior of our models in a real tutoring setting, we conduct a user study using expert annotators and find a significantly large number of model reasoning errors in 45% of conversations. Finally, we connect our findings to outline future work.

Socratic questioning is an educational method that allows students to discover answers to complex problems by asking them a series of thoughtful questions. Generation of didactically sound questions is challenging, requiring understanding of the reasoning process involved in the problem. We hypothesize that such questioning strategy can not only enhance the human performance, but also assist the math word problem (MWP) solvers.In this work, we explore the ability of large language models (LMs) in generating sequential questions for guiding math word problem-solving. We propose various guided question generation schemes based on input conditioning and reinforcement learning.On both automatic and human quality evaluations, we find that LMs constrained with desirable question properties generate superior questions and improve the overall performance of a math word problem solver. We conduct a preliminary user study to examine the potential value of such question generation models in the education domain. Results suggest that the difficulty level of problems plays an important role in determining whether questioning improves or hinders human performance. We discuss the future of using such questioning strategies in education.