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The most successful teams aren’t the ones with the most sophisticated tools or the most advanced models—they’re the ones that master the fundamentals of measurement, iteration, and learning.
The Most Common Mistake: Skipping Error Analysis
The Error Analysis Process
Bottom-Up Versus Top-Down Analysis
The Most Important AI Investment: A Simple Data Viewer
Empower Domain Experts To Write Prompts
Build Bridges, Not Gatekeepers
Tips For Communicating With Domain Experts
Bootstrapping Your AI With Synthetic Data Is Effective (Even With Zero Users)
A Framework for Generating Realistic Test Data
Guidelines for Using Synthetic Data
Maintaining Trust In Evals Is Critical
Understanding Criteria Drift
Creating Trustworthy Evaluation Systems
1. Favor Binary Decisions Over Arbitrary Scales
2. Enhance Binary Judgments With Detailed Critiques
3. Measure Alignment Between Automated Evals and Human Judgment
Scaling Without Losing Trust
Your AI Roadmap Should Count Experiments, Not Features
Experiments Versus Features
The Foundation: Evaluation Infrastructure
Communicating This to Stakeholders
Build a Culture of Experimentation Through Failure Sharing
A Better Way Forward
Resources for Going Deeper
If you’d like to explore these topics further, here are some resources that might help:
- Author’s blog for more content on AI evaluation and improvement. My other posts dive into more technical detail on topics such as constructing effective LLM judges, implementing evaluation systems, and other aspects of AI development.1 Also check out the blogs of Shreya Shankar and Eugene Yan, who are also great sources of information on these topics.
- A course I’m teaching, Rapidly Improve AI Products with Evals, with Shreya Shankar. It provides hands-on experience with techniques such as error analysis, synthetic data generation, and building trustworthy evaluation systems, and includes practical exercises and personalized instruction through office hours.
- If you’re looking for hands-on guidance specific to your organization’s needs, you can learn more about working with me at Parlance Labs.

