
The Inbox Is the Real Agent Benchmark
Email is the hardest test for an AI agent: ambiguous intent, irreversible actions, and real trust. Here's why most demos quietly avoid it.
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Practical writing on productivity, AI, and building software.

Email is the hardest test for an AI agent: ambiguous intent, irreversible actions, and real trust. Here's why most demos quietly avoid it.

Most multimodal benchmarks test isolated perception, not the chained document-to-action tasks agents actually perform. Here's what better evaluation looks like.

Spreadsheet edits demand cell-level, deterministic evaluation — accuracy, reversibility, and formula integrity — not vibes-based scoring.

Calling AI agents 'digital employees' quietly erodes human accountability. Treat them as orchestrated, audited tools instead — here's how and why.

A diagnostic framework for why agentic workflows degrade over multi-step tasks — context loss, tool errors, and goal drift — plus concrete mitigations.

Reasoning depth should scale with task difficulty. Here's when chain-of-thought helps, when it hurts, and how to spend reasoning tokens wisely.

The clever one-liner prompt is fading. Durable AI work needs specifications: constraints, examples, and acceptance criteria you can reuse.

A decision framework for choosing constrained AI workflows over open-ended agents — and the specific conditions that justify going agentic.

A rigorous time-and-error log of AI in real knowledge work — separating genuine wins from rework and the hidden review tax.

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.
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