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Evaluating AI Applications

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Evaluation Foundations and Success Criteria

1. What is an AI application evaluation, and why are normal unit tests not enough?

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2. How do you define an evaluation objective before choosing metrics?

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3. What should one evaluation case contain?

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4. What is the difference between offline and online evaluation?

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5. Why should evaluations be task-specific instead of relying on one generic quality score?

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6. How do you build a useful failure taxonomy for an AI feature?

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Datasets, Labels, and Reproducibility

7. What makes an evaluation dataset representative?

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8. What is a golden dataset, and how should it be used?

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9. How do you split evaluation data and reduce contamination?

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10. When is synthetic evaluation data useful, and what can go wrong?

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11. How do you write a labeling rubric that humans can apply consistently?

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12. How do you version datasets and make evaluation runs reproducible?

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Graders, Comparison, and Calibration

13. Which checks should be deterministic before using a model grader?

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14. When should you use an LLM as a judge?

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15. When is pairwise comparison better than scoring one answer?

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16. How do you calibrate an automated grader against human judgment?

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17. How do bias and variance affect AI evaluation results?

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18. What is grader hacking, and how do you detect it?

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RAG and End-to-End System Evaluation

19. Why should RAG retrieval and generation be evaluated separately?

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20. Which metrics help evaluate ranked retrieval results?

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21. How do groundedness, relevance, and completeness differ in a RAG evaluation?

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22. How do you evaluate chunking, top-k, and reranking changes?

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23. How do you evaluate agents with tools without grading only the final answer?

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24. How do you include latency, cost, and reliability in evaluation gates?

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Regression, Experiments, and Production Feedback

25. What belongs in a CI regression suite for an AI feature?

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26. How do you compare prompt, model, or configuration changes fairly?

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27. How do you set release thresholds without hiding slice regressions?

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28. How do you turn production feedback into better evaluations?

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29. How do you detect data, model, and behavior drift in production?

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30. How do you design a safe canary or A/B test for an AI change?

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Statistical Confidence

31. How do sample size, confidence intervals, and repeated trials affect an AI evaluation?

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