Standard single-turn, static benchmarks fall short in evaluating the nuanced capabilities of Large Language Models (LLMs) on complex tasks such as software engineering. In this work, we propose a novel interactive evaluation framework that assesses LLMs on multi-requirement programming tasks through structured, feedback-driven dialogue. Each task is modeled as a requirement dependency graph, and an "interviewer" LLM, aware of the ground-truth solution, provides minimal, targeted hints to an "interviewee" model to help correct errors and fulfill target constraints. This dynamic protocol enables fine-grained diagnostic insights into model behavior, uncovering strengths and systematic weaknesses that static benchmarks fail to measure. We build on DevAI, a benchmark of 55 curated programming tasks, by adding ground-truth solutions and evaluating the relevance and utility of interviewer hints through expert annotation. Our results highlight the importance of dynamic evaluation in advancing the development of collaborative code-generating agents.