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Traditional benchmarks relied on programmatic verification of narrow, surface-level constraints, but real-world instruction following and agentic tasks demand assessment of nuanced, context-dependent behaviors that resist simple scripted checks. We present a systematic analysis of expert-curated rubric-based evaluation as an alternative paradigm, drawing on empirical evidence from two domains: complex instruction following and enterprise agentic tasks. We first articulate five design principles for constructing high-quality rubrics, including Maximum Viable Atomicity, intent-aware criterion design, and iterative LLM-judge calibration. To validate these principles, we introduce ComplexConstraints, a new expert-curated instruction-following dataset in which each prompt is paired with 10-40 atomic rubric criteria. 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