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PostHeaderIcon [DevoxxFR2026] Measuring the Unmeasurable: Evaluating Generative AI Systems

Lecturer

Erin Pacquetet is an expert in AI evaluation and product development at SCIAM, a Paris-based consulting firm. With a background in linguistics and extensive experience guiding enterprises through the complexities of deploying generative AI applications, she specializes in bridging technical implementation with business requirements and robust quality assurance.

Abstract

Generative AI systems promise transformative capabilities but present unique evaluation challenges due to their creative and unpredictable nature. Erin Pacquetet addresses this paradox by outlining comprehensive strategies for assessing systems that blend linguistic fluidity with strict factual accuracy. Using a Retrieval-Augmented Generation (RAG) chatbot as a running case study, the presentation examines limitations of traditional metrics, the role of LLM-as-a-judge approaches alongside their inherent biases, the necessity of human evaluation, and continuous monitoring to detect drift. Attendees gain practical frameworks for building reproducible evaluation pipelines that balance innovation with reliability in production environments.

The Fundamental Challenge of Evaluating Generative Systems

Generative AI introduces a core tension between creativity and control. Organizations adopt large language models precisely because they handle diverse, uncontrolled inputs and produce personalized outputs. Yet this very strength complicates evaluation. Traditional deterministic testing works for rule-based systems but falls short when outputs vary naturally while needing to remain accurate, relevant, and safe.

In the case study of an insurance company’s customer-facing RAG chatbot, the system must answer questions about policies while adhering to brand tone, regulatory constraints, and response length limits. A single question like “Is home insurance mandatory for tenants in France?” could yield multiple valid responses of varying quality. Evaluation must therefore move beyond binary correctness to nuanced assessment across multiple dimensions.

Effective evaluation pipelines transform qualitative judgments into quantitative, scalable measurements. This requires simulating realistic inputs, generating outputs, and assessing them against well-defined criteria. The process must cover ideal scenarios, expected real-world usage, and adversarial cases to ensure robustness before production deployment.

Simulating Inputs: Ideal, Realistic, and Adversarial Scenarios

The foundation of any evaluation lies in a carefully constructed dataset representing the full spectrum of potential interactions. For the insurance chatbot, inputs fall into three categories.

Ideal inputs are perfectly formed questions with clear intent and complete context, such as grammatically correct inquiries directly related to covered products. These establish baseline performance and set high acceptance thresholds.

Realistic inputs mirror actual user behavior: keyword-based queries, vague phrasing, oral-style language, partial context, or minor errors. Testing these ensures the system handles the messy reality of production traffic rather than sanitized examples.

Adversarial inputs probe vulnerabilities: prompt injections, attempts to elicit harmful content, off-topic questions, or malicious efforts to bypass safeguards. These reveal security weaknesses and edge cases that could damage reputation or expose risks.

Creating this dataset demands collaboration between technical teams and domain experts. Business stakeholders define what constitutes success for each category, translating abstract requirements into concrete examples. This exercise often reveals inconsistencies in initial specifications, forcing clarification before development advances.

The resulting evaluation dataset serves as both a benchmark and a living artifact. It evolves with the product, incorporating new failure modes discovered in production and expanding coverage as usage patterns emerge.

Generating and Assessing Outputs: Metrics and Human Judgment

Once inputs are prepared, the system generates outputs for evaluation. Assessment occurs along two primary axes: output quality and operational performance.

Output quality encompasses factual accuracy, relevance to the query, completeness of information, and safety. For the RAG chatbot, responses must draw correctly from policy documents, address the specific question asked, provide sufficient detail without excess length, and maintain an appropriate empathetic tone.

Traditional metrics prove insufficient. String matching fails to capture semantic equivalence across varied phrasings. Semantic similarity measures can overlook critical omissions or subtle inaccuracies. Probabilistic approaches, particularly LLM-as-a-judge, offer greater flexibility by leveraging models to analyze outputs against detailed criteria.

A well-crafted judge prompt might instruct the model to identify contradictions or omissions between a generated response and a reference answer, returning a binary judgment. This constrains the evaluation task sufficiently to reduce variance while maintaining nuance. Multiple specialized judges can target different aspects: one for factual consistency, another for tone alignment, and a third for regulatory compliance.

Human evaluation remains essential for validation. Domain experts review samples to calibrate automated metrics, ensuring alignment between machine judgments and business expectations. This human-in-the-loop process establishes confidence thresholds for each metric.

Operational metrics complement quality assessment. Response latency, cost per inference, and system stability must meet production requirements. A perfectly accurate but slow response fails as a product. Monitoring these dimensions alongside quality creates a holistic view of system readiness.

Building and Maintaining Evaluation Pipelines

A complete pipeline integrates input simulation, output generation, and multi-faceted assessment into an automated workflow. Teams execute evaluations frequently: after prompt modifications during development, before major releases, and continuously in production to detect regression or drift.

The evaluation dataset evolves as the central reference point. Production logs reveal new query patterns or failure modes, which teams incorporate to strengthen coverage. Regular human review sessions ensure metrics remain aligned with changing business needs and user expectations.

For the insurance chatbot, this meant balancing completeness against brevity, factual precision against approachable language, and safety against helpfulness. The dataset captured these trade-offs explicitly, allowing systematic optimization rather than guesswork.

Challenges persist. Judge models can inherit biases or exhibit inconsistency. Human evaluators introduce subjectivity. Thresholds require careful tuning to avoid both false confidence and excessive caution. Success demands iterative refinement and cross-functional collaboration.

From Evaluation to Production Confidence

Robust evaluation bridges the gap between promising prototypes and reliable production systems. By systematically addressing the inherent variability of generative outputs, teams build the confidence necessary for deployment.

The insurance chatbot case demonstrates that evaluation is not merely technical validation but a strategic discipline. It forces clarification of requirements, surfaces hidden assumptions, and creates shared understanding across technical and business stakeholders.

As generative AI proliferates, organizations that master evaluation gain competitive advantage. They deploy innovative capabilities with appropriate safeguards, iterating rapidly while maintaining quality. The discipline transforms the “unmeasurable” into something manageable, turning potential risk into sustainable value.

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