Mixed-Initiative Context: Structuring and Managing Context for Human-AI Collaboration

Collaborations with Generative AI often begin with a short prompt and end with an opaque output, leaving implicit who was involved, what task was being pursued, which resources were used, and which constraints should have shaped the process. This limited contextual explicitness hinders trust, traceability, and accountability, particularly when Generative AI is embedded in information-intensive workflows such as search, querying, and profile management. This paper introduces From Prompts to Context, an ontology-driven framework for representing Human-Generative AI collaboration. Its core component, the Contextual Collaboration AI Ontology (CCAI), models key elements of collaboration - including tasks, agent roles, resources, and constraints - as a shared machine-interpretable vocabulary. By combining populated CCAI instances with SPARQL-based context retrieval in operational workflows, the framework turns otherwise ephemeral prompt-response interactions into structured and queryable collaboration traces linking prompts, outputs, and their surrounding context. The approach is illustrated through a case study involving a software development team building a competency-based education feature for viewing and updating learner competency profiles. The case study shows how the framework can support the representation and documentation of collaboration episodes across requirements analysis, design, implementation, and testing. Within this setting, the results indicate that explicit collaboration modelling helps make task context more explicit, improves the traceability of AI-generated contributions, and supports more transparent and accountable Human-Generative AI practices. We conclude by outlining design principles for future Human-Generative AI systems that emphasise not only output quality, but also the explicit representation of the collaborative context in which outputs are produced.

The quality of AI-generated output is often attributed to prompting technique, but extensive empirical observation suggests that context completeness may be more strongly associated with output quality. This paper introduces Context Engineering, a structured methodology for assembling, declaring, and sequencing the complete informational payload that accompanies a prompt to an AI tool. Context Engineering defines a five-role context package structure (Authority, Exemplar, Constraint, Rubric, Metadata), applies a staged four-phase pipeline (Reviewer to Design to Builder to Auditor), and applies formal models from reliability engineering and information theory as post hoc interpretive lenses on context quality. In an observational study of 200 documented interactions across four AI tools (Claude, ChatGPT, Cowork, Codex), incomplete context was associated with 72% of iteration cycles. Structured context assembly was associated with a reduction from 3.8 to 2.0 average iteration cycles per task and an improvement in first-pass acceptance from 32% to 55%. Among structured interactions, 110 of 200 were accepted on first pass compared with 16 of 50 baseline interactions; when iteration was permitted, the final success rate reached 91.5% (183 of 200). These results are observational and reflect a single-operator dataset without controlled comparison. Preliminary corroboration is provided by a companion production automation system with eleven operating lanes and 2,132 classified tickets.

As humans increasingly rely on multiround conversational AI for high stakes decisions, principled frameworks are needed to ensure such interactions reliably improve decision quality. We adopt a human centric view governed by two principles: counterfactual harm, ensuring the AI does not undermine human strengths, and complementarity, ensuring it adds value where the human is prone to err. We formalize these concepts via user defined rules, allowing users to specify exactly what harm and complementarity mean for their specific task. We then introduce an online, distribution free algorithm with finite sample guarantees that enforces the user-specified constraints over the collaboration dynamics. We evaluate our framework across two interactive settings: LLM simulated collaboration on a medical diagnostic task and a human crowdsourcing study on a pictorial reasoning task. We show that our online procedure maintains prescribed counterfactual harm and complementarity violation rates even under nonstationary interaction dynamics. Moreover, tightening or loosening these constraints produces predictable shifts in downstream human accuracy, confirming that the two principles serve as practical levers for steering multi-round collaboration toward better decision quality without the need to model or constrain human behavior.