ConvoDojo: Structured LLM-based Sparring Partners for Difficult Workplace Conversations.

Abstract

Large language models (LLMs) often exhibit sycophancy, optimizing for agreement over productive challenge, which severely limits their utility in domains like professional skills training, where growth requires pushback. We introduce, ConvoDojo, a novel conversational AI platform for practicing difficult workplace conversations, engineered not merely as a commercial training application but also as a flexible, instrumented research platform for evaluating conversational AI strategies. ConvoDojo repurposes LLMs as structured sparring partners to support skill development in difficult workplace conversations (e.g., performance feedback, conflict resolution), addressing the reported managerial tendency to avoid them. This paper showcases the platform and presents an evaluation of how key conversational user interface (CUI) design elements, namely, the addition of structured feedback and upfront instructional scaffolding, impact managers’ learning. Results show that ConvoDojo is highly engaging and promotes user reflection. We demonstrate how theory-informed dialogue and adaptive pushback can transform an LLM into an effective, measurable tool for complex communication skills development.