Project Kaleidoscope: Contextual, Human-Aligned Evaluation for Real-World AI Applications

Generative AI systems achieve impressive performance on standard benchmarks yet fail to deliver real-world utility, a disconnect we identify across 28 deployment cases spanning education, healthcare, software engineering, and law. We argue that this benchmark utility gap arises from three recurring failures in evaluation practice: proxy displacement, temporal collapse, and distributional concealment. Motivated by these observations, we argue that generative AI evaluation requires a paradigm shift from static benchmark-centered transparency toward stakeholder, goal, and context-conditioned utility transparency grounded in human outcome trajectories. Existing evaluations primarily characterize properties of model outputs, while deployment success depends on whether interaction with AI improves stakeholders' ability to achieve their goals over time. The missing construct is therefore utility: the change in a stakeholder's capability induced through sustained interaction with an AI system within a deployment context. To operationalize this perspective, we propose SCU-GenEval, a four-stage evaluation framework consisting of stakeholder-goal mapping, construct-indicator specification, mechanism modeling, and longitudinal utility measurement. To make these stages practically deployable, we introduce three supporting instruments: structured deployment protocols, context-conditioned user simulators, and persona- and goal-conditioned proxy metrics. We conclude with domain-specific calls to action, arguing that progress in generative AI must be evaluated through measurable improvements in human outcomes rather than benchmark performance alone.

AI measurement science has a wide variety of methodologies and measurements for comparing AI systems, resulting in what often appear to be "apples-to-oranges" comparisons across AI evaluations. To move toward "apples-to-apples" comparisons in real-world AI evaluations, this work advocates for methodological transparency in evaluation scenarios, operational grounding, and human-centered design (HCD) principles. We propose a repeatable process for transforming high-level use cases to detailed scenarios by eliciting use cases from subject matter experts (SMEs) via a structured AI Use Case Worksheet with six key elements: use case, sector, user (direct and indirect), intended outcomes, expected impacts (positive and negative), and KPIs and metrics. We demonstrate utility of the worksheet and process in the U.S. financial services sector. This paper reports on example high-level AI use cases identified by financial services sector SMEs: cyber defense enablement, developer productivity, financial crime aggregation, suspicious activity report (SAR) filing, credit memo generation, and internal call center support. These AI use cases provided are illustrative of the process and not exhaustive. Central to our work is a three-stage expansion pipeline combining LLM prompting with human reviews to generate 107 scenarios from those use cases elicited from SMEs. This process integrates iterative human reviews at every juncture to ensure operational grounding: for scenario titles and descriptions; for core scenario elements like users, benefits and risks, and metrics; and for scenario narratives and evaluation objectives. Human checkpoints ensure scenarios remain reflective of real-world usage and human needs. We describe a validation rubric to assess scenario quality. By defining key scenario components, this work supports a more consistent and meaningful paradigm for human-centered AI evaluations.

AI agents must be evaluated as behavioral systems, not as isolated response generators. They reason across turns, call tools, preserve context, follow policies, and act under uncertainty. Existing methods provide useful but fragmented signals: benchmarks measure fixed capabilities, Human-in-the-Loop review preserves expert judgment but does not scale easily, LLM-as-judge methods depend on evaluator design, red teaming is often episodic, and trace auditing requires explicit evidence rules. This paper introduces Human-on-the-Bridge (HOB), a scalable evaluation paradigm for agentic AI. HOB places human expertise upstream, where experts curate reusable evaluation intelligence before testing begins, including domain context, Red-Team Traps, Juror Personas, scoring guidelines, audit rules, and fallback policies. ProofAgent Harness then executes this curated intelligence repeatedly through multi-turn adversarial evaluations, trace capture, multi-juror scoring, and evidence-linked reporting. We evaluate HOB through symmetric and cost-efficient asymmetric settings across frontier LLM-based agents and Harness LLM tiers. The study covers 23,500 agent turns and produces evidence-linked findings across finance, healthcare, and code generation. The results show that HOB can amplify evaluation quality without requiring equally large evaluator models, allowing smaller Harness LLMs to challenge agents built on frontier LLM backbones. The evaluation surfaces failures often missed by static benchmarks and single-evaluator scoring, including phantom tool-call claims, missing mandatory tool calls, policy drift, manipulation paths, and safe but non-resolving refusals. These findings support HOB as a paradigm for scaling human-curated evaluation intelligence, where expert judgment is encoded upfront and reused across repeated agent evaluations rather than applied manually inside every run.