Matthew Holmes

Matthew Holmes, Thiago Lacerda, Reva Schwartz

With many organizations struggling to gain value from AI deployments, pressure to evaluate AI in an informed manner has intensified. Status quo AI evaluation approaches often mask the operational realities that ultimately determine deployment success, making it difficult for organizational decision makers to know whether and how AI tools will deliver durable value. We introduce and describe context specification as a process to support and inform this decision making process. Context specification turns diffuse stakeholder perspectives about what matters in a given setting into clear, named constructs: explicit definitions of the properties, behaviors, and outcomes that evaluations aim to capture, so they can be observed and measured in context. The process serves as a foundational roadmap for evaluating what AI systems are likely to do in the deployment contexts that organizations actually manage.

Reva Schwartz, Carina Westling, Morgan Briggs et al.

This paper proposes CIRCLE, a six-stage, lifecycle-based framework to bridge the reality gap between model-centric performance metrics and AI's materialized outcomes in deployment. While existing frameworks like MLOps focus on system stability and benchmarks measure abstract capabilities, decision-makers outside the AI stack lack systematic evidence about the behavior of AI technologies under real-world user variability and constraints. CIRCLE operationalizes the Validation phase of TEVV (Test, Evaluation, Verification, and Validation) by formalizing the translation of stakeholder concerns outside the stack into measurable signals. Unlike participatory design, which often remains localized, or algorithmic audits, which are often retrospective, CIRCLE provides a structured, prospective protocol for linking context-sensitive qualitative insights to scalable quantitative metrics. By integrating methods such as field testing, red teaming, and longitudinal studies into a coordinated pipeline, CIRCLE produces systematic knowledge: evidence that is comparable across sites yet sensitive to local context. This can enable governance based on materialized downstream effects rather than theoretical capabilities.