Evaluations (Evals) are a deployment bottleneck for real-world AI applications: public benchmarks rarely match a team's users, context, or policies, and human review is often tedious to scale. Motivated by our work with AI applications in the public sector, this project addresses recurring evaluation challenges encountered when applications must satisfy local policy and governance requirements. We present Kaleidoscope, an integrated workflow for contextual functional evaluation that links persona-based test generation, contextualized rubrics, and human review for reliability-gated automated scoring. Generated test cases are scored against application-specific rubrics; human annotations provide reviewable labels; and LLM judges automate scoring only when their agreement with those labels meets a configured threshold. Kaleidoscope is therefore a practical, inspectable, iterative workflow for product teams. We report early evidence from a three-week pilot across four organizational use cases and custom-rubric judge experiments on 108 annotated Q\&A pairs spanning four domains and 14 evaluation dimensions. The results highlight useful features for end-to-end reliable, automated scoring.
Skills are becoming a reusable operational layer for LLM agents, encoding SOPs, domain rules, tool workflows, scripts, and validation routines. In realistic skill repositories, overlapping skills make reliable skill-use difficult. Final verifier success is too coarse for both evaluation and training, since an agent may pass through trial and error while selecting distractor skills, skipping required steps, composing workflows incorrectly or omitting final checks. We introduce SkillCoach, a self-evolving rubric framework for evaluating and enhancing agentic skill-use. SkillCoach derives skill-grounded process rubrics from real rollouts and evaluates trajectories along four dimensions: skill selection, skill following, skill composition, and skill-grounded reflection. It keeps the external verifier as a separate outcome signal, allowing process quality to be distinguished from accidental task success. The evolved rubrics further serve as process supervision for selecting high-quality training trajectories. Experiments show that evolved rubrics substantially improve evaluation quality, expose failures hidden by final accuracy, and provide stronger supervision signals than outcome-only filtering for enhancing agentic skill-use.