134 posts tagged with "evals"

The prompt for our support agent was 2,400 tokens when I inherited it, and the engineer who wrote it had left the company. Every instruction in it was load-bearing for some production behavior, but nobody could tell me which ones. A bullet about "always restate the user's problem before answering" looked like filler until we deleted it and CSAT dropped four points in a week. The prompt was, it turned out, the specification. It was also the implementation. It was also the test suite — implicit, unwritten, living only in the head of an engineer who no longer worked there.

That is the endgame of prompt-as-spec. The prompt is both what the agent should do and how it does it, and the two become indistinguishable the moment the prompt outgrows a single author. You can't refactor it because you don't know which lines encode requirements and which encode mere hints. You can't review a change because there's no artifact the change is a diff against. You can't onboard anyone to own it because ownership means "having read the whole thing recently and remembering why each clause is there," which is a six-month investment nobody authorizes.

Spec-first flips the ordering. The contract — inputs, outputs, invariants, error cases, refusal semantics, escalation triggers — is a first-class artifact that precedes the prompt and constrains every revision. Prompt edits become diffs against a spec, not rewrites of the spec itself. The shift sounds bureaucratic until you see what it unlocks: evals that come from the spec rather than the other way around, reviews that take minutes instead of afternoons, and the eventual ability to let a new engineer own the surface without a six-month apprenticeship.

Ask an agent team what their tool-call success rate is and you will get an answer. Ask them what their tool-hallucination rate is and the room goes quiet. Most teams do not track it, and the ones who do usually only count the catastrophic version — a function name that does not exist in the catalog — while the quieter, more expensive variants travel through production unmetered.

A hallucinated tool call is not only when the model invents delete_orphaned_users(older_than="30d") and your dispatcher throws ToolNotFoundError. That is the easy case. The harder case is when the fabricated call shadows into an adjacent real tool through fuzzy matching, or when the tool name is correct but the agent invents an argument your schema happily accepts because you marked it optional. Both of those pass your "did a tool call succeed" dashboard. Neither is what the user asked for.

The common failure mode isn't building AI features that don't work. It's shipping AI features without any way to know whether they work. And the reason teams skip evaluation infrastructure isn't laziness — it's that building evals requires labeled data, and on day one you have none.

This is the cold start problem for evals. To get useful signal, you need your system running in production. To deploy with confidence, you need evaluation infrastructure first. The circular dependency is real, and it causes teams to do one of three things: ship without evals and discover failures in production, delay shipping while hand-labeling data for months, or use synthetic evals — with all the risks that entails.

This post is about the third path done correctly. Synthetic eval bootstrapping works, but only if you understand what it cannot detect and build around those blind spots from the start.

Teams building LLM applications consistently make the same mistake: they wait for enough labeled data before investing in evaluation infrastructure. They tell themselves they need 5,000 examples. Or 10,000. The eval system stays on the backlog while "vibe checks" substitute for measurement. A ZenML analysis of 1,200 production deployments found that informal vibe checks remain common even in mature deployments — and many teams never graduate to systematic evals at all.

The data-size intuition is borrowed from classical ML, where more labeled examples reliably improved model performance. For LLM evaluation, it is largely wrong. Research on sparse benchmarks demonstrates that 20–40 carefully selected items reliably estimate full-benchmark rankings, and 100 items produce mean absolute error below 1% compared to thousands. The problem is not data volume. The problem is that most teams skip the structured process that makes small evaluation sets trustworthy.

This post covers what that process actually looks like: how to select the right examples through active learning, how to generate noisy labels at scale with weak supervision, how to bootstrap with LLM judges, and how to know when your small eval set is ready to use.

Your eval suite scores 91%. Users report the system feels unreliable. The post-mortem reveals the culprit: you used GPT-4o to both generate responses and grade them. The model was judging its own mirror image, and it liked what it saw.

This is the judge model independence problem. It is more widespread than most teams realize, the score inflation it produces is large enough to matter, and the fix is neither complicated nor expensive. But you have to know to look for it.

Most teams discover their retry problem when the invoice shows up. The agent "worked"; latency dashboards stayed green; error rates looked fine. Then finance asks why inference spend doubled this month, and someone finally reads the logs. It turns out that 20% of the tool calls in a 3-step agent were quietly retrying, each retry replayed the full prompt history, and the bill had been ramping for weeks.

The math on this is not mysterious, but it is aggressively counterintuitive. A 20% per-step retry rate sounds tolerable — most engineers would glance at it and move on. The actual token cost, once you factor in how modern agent frameworks retry, lands much closer to 2x than 1.2x. And the failure mode is invisible to every metric teams typically watch.

Retry budgets — an old idea from Google SRE work — are the cleanest fix. But the LLM version of the pattern needs tweaking, because tokens don't behave like RPCs.

Your team spent three weeks building a rigorous eval suite. It covers edge cases. It includes adversarial examples. The LLM-as-judge scores 92% across all dimensions. You ship.

Then the support tickets start. Users say the AI "doesn't understand what they're asking." Session abandonment is up 30%. Satisfaction scores come back at 41%.

This gap — between eval performance and real-world outcomes — is the most common failure mode in production AI systems today. It's not a model problem. It's a measurement problem.

A team built an AI research assistant using Claude. They iterated on the prompt for three weeks, demo'd it to stakeholders, and launched it feeling confident. Two months later they discovered that the assistant had been silently hallucinating citations across roughly 30% of outputs — a failure mode no one had tested for because the eval suite was built after the prompt had already "felt right" in demos.

This pattern is the rule, not the exception. The LLM development industry has largely adopted test-driven development vocabulary — evals, regression suites, golden datasets, LLM-as-judge — while ignoring the most important rule TDD establishes: write the test before the implementation, not after.

Here is how to do that correctly, and the three places where the TDD analogy breaks down so badly that following it literally will make your system worse.

Most teams building LLM applications fall into one of two failure modes. The first is building no evals at all and shipping features on vibes. The second is building elaborate evaluation infrastructure before they understand what they're actually trying to measure. Both are expensive mistakes.

The teams that do evals well share a common approach: they start by looking at data, not by building systems. Error analysis comes before evaluation automation. Human judgment grounds the metrics before any automated judge is trusted. And they treat evaluation not as a milestone to cross but as a continuous discipline that evolves alongside the product.

This is what evals actually look like in practice — the decisions that matter, the patterns that waste effort, and the tradeoffs that aren't obvious until you've been burned.

Most teams build their LLM evaluators in the wrong order. They write criteria, then look at data. That inversion is the root cause of miscalibrated evals, and it's almost universal in teams shipping their first AI product. The criteria sound reasonable on paper — "the response should be accurate, helpful, and concise" — but when you apply them to real model outputs, you discover the rubric doesn't match what you actually care about. You end up with an evaluator that grades things you're not measuring and misses failures that matter.

The fix isn't a better rubric. It's a different workflow: look at the data first, define criteria second, and then validate your evaluator against human judgment before trusting it to run unsupervised.

Most teams building LLM systems start with the wrong question. They ask "how do I evaluate this?" before understanding what actually breaks. Then they spend weeks building eval infrastructure that measures the wrong things, achieve 90%+ pass rates immediately, and ship products that users hate. The evaluations weren't wrong—they just weren't measuring failure.

Effective eval engineering isn't primarily about infrastructure. It's about developing a precise, shared understanding of what "good" means for your specific system. The infrastructure is almost incidental. In mature LLM teams, 60–80% of development time goes toward error analysis and evaluation—not feature work. That ratio surprises most engineers until they've shipped a broken model to production and spent a week debugging what went wrong.

Every AI product demo looks great. The model generates something plausible, the stakeholders nod along, and everyone leaves the meeting feeling optimistic. Then the product ships, real users appear, and things start going sideways in ways nobody anticipated. The team scrambles to fix one failure mode, inadvertently creates another, and after weeks of whack-a-mole, the prompt has grown into a 2,000-token monster that nobody fully understands anymore.

The root cause is almost always the same: no evaluation system. Teams that ship reliable AI products build evals early and treat them as infrastructure, not an afterthought. Teams that stall treat evaluation as something to worry about "once the product is more mature." By then, they're already stuck.