LLMs are increasingly presented as collaborators in programming, design, writing, and analysis. Yet the practical experience of working with them often falls short of this promise. In many settings, users must diagnose misunderstandings, reconstruct missing assumptions, and repeatedly repair misaligned responses. This poster introduces a conceptual framework for understanding why such collaboration remains fragile. Drawing on a constructivist grounded theory analysis of 16 interviews with designers, developers, and applied AI practitioners working on LLM-enabled systems, and informed by literature on human-AI collaboration, we argue that stable collaboration depends not only on model capability but on the interaction's grounding conditions. We distinguish three recurrent structures of human-AI work: one-shot assistance, weak collaboration with asymmetric repair, and grounded collaboration. We propose that collaboration breaks down when the appearance of partnership outpaces the grounding capacity of the interaction and contribute a framework for discussing grounding, repair, and interaction structure in LLM-enabled work.

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