Predicting difficulty of questions is crucial for technical interviews. However, such questions are long-form and more open-ended than factoid and multiple choice questions explored so far for question difficulty prediction. Existing models also require large volumes of candidate response data for training. We study weak-supervision and use unsupervised algorithms for both question generation and difficulty prediction. We create a dataset of interview questions with difficulty scores for deep learning and use it to evaluate SOTA models for question difficulty prediction trained using weak supervision. Our analysis brings out the task’s difficulty as well as the promise of weak supervision for it.

We explore the task of generating long-form technical questions from textbooks. Semi-structured metadata of a textbook — the table of contents and the index — provide rich cues for technical question generation. Existing literature for long-form question generation focuses mostly on reading comprehension assessment, and does not use semi-structured metadata for question generation. We design unsupervised template based algorithms for generating questions based on structural and contextual patterns in the index and ToC. We evaluate our approach on textbooks on diverse subjects and show that our approach generates high quality questions of diverse types. We show that, in comparison, zero-shot question generation using pre-trained LLMs on the same meta-data has much poorer quality.