Guardrails and evals people can trust
23 Sep 2026
In this moment:
Maneesh Maddala
AI Chapter
In the session "Guardrails & Evals: Keeping Your AI Skills Honest" from Maneesh Maddala in the AI Chapter
Writing Guardrails:
1. Make it testable: "A rule without a test is a suggestion. Pair every guardrail with an eval."
2. Use a real failure: "Build guardrails from failures you have seen, not hypothetical ones."
3. Make enforcement predictable: "When the same violation sometimes blocks and sometimes passes, people cannot trust the rule."
1. Make it testable: "A rule without a test is a suggestion. Pair every guardrail with an eval."
2. Use a real failure: "Build guardrails from failures you have seen, not hypothetical ones."
3. Make enforcement predictable: "When the same violation sometimes blocks and sometimes passes, people cannot trust the rule."
Writing Evals:
1. Match cost to evidence: "Run deterministic checks on every commit. Use an LLM judge only when the answer needs judgment."
2. Include one attack attempt: "Test at least one prompt injection or adversarial request."
3. Measure repeated runs: (This box is highlighted with an orange border) "pass@k = one success in k tries. pass^k = every run passes (needed for guardrails)"
1. Match cost to evidence: "Run deterministic checks on every commit. Use an LLM judge only when the answer needs judgment."
2. Include one attack attempt: "Test at least one prompt injection or adversarial request."
3. Measure repeated runs: (This box is highlighted with an orange border) "pass@k = one success in k tries. pass^k = every run passes (needed for guardrails)"
Rosie Sherry
CEO & Founder at Ministry of Testing
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I've been working in the software testing and quality engineering space since the year 2000 whilst also combining it with my love for education and community. It turns out quality, community and education go nicely hand in hand.
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