
Evaluating AI Output When There's No Right Answer
How to build evals for subjective knowledge work — emails, summaries, docs — using rubrics, pairwise comparison, and human-in-the-loop sampling.

How to build evals for subjective knowledge work — emails, summaries, docs — using rubrics, pairwise comparison, and human-in-the-loop sampling.

A concrete audit of where your prompts, files, and context actually travel across AI assistants — and the data boundaries every enterprise should demand.

When a RAG pipeline gives bad answers, the LLM usually isn't the problem. Retrieval is. Here's where chunking, ranking, and recall actually break.

Public leaderboards reward the wrong things for agentic work. Here's a practical eval harness built around real task completion and side-effect safety.

Why LLMs should generate and execute formulas instead of hallucinating math — plus concrete patterns for verifiable spreadsheet automation.

Email looks routine, but it's the toughest environment for autonomy: ambiguous intent, irreversible sends, and tangled threading state. Here's what reliable inbox automation really takes.

Stuffing a million tokens into a prompt degrades reasoning more than it helps. The real skill is curating what the model actually attends to.

A practical decision framework for choosing retrieval, full-context, or hybrid approaches based on data volatility, cost, and accuracy.

When agents read and draft your email, success isn't an empty inbox — it's well-designed triage rules, escalation thresholds, and approval boundaries.

Email threads encode decisions, commitments, and relationships better than any wiki — making your inbox the highest-signal grounding source for an AI assistant.

Practical patterns for coaxing consistent, spreadsheet-ready data out of LLMs — schema enforcement, validation loops, and the pitfalls that quietly corrupt your tables.

Pure vector search over personal files stumbles on recency, permissions, and exact terms. Hybrid retrieval plus metadata is the fix.
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