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1:1 session
Advanced System Prompts, Structured Outputs & Evaluation Frameworks
Target audience: Technical product managers, developers, and operations engineers.
Applicable duration: 60 mins · 120 mins
When prompt engineering scales into automated software products and enterprise workflows, manual "eyeball" testing of prompt revisions becomes unsustainable. A tweak that improves one customer query may silently break twelve others. Transitioning prompt engineering into a reliable discipline requires automated evaluation frameworks and strict schema enforcement.
In this advanced 1:1 session, you will learn to author production system prompts that withstand prompt injection, enforce strict JSON Schema outputs, and set up automated benchmarking pipelines to score prompt iterations systematically.
What you will learn
- Production System Prompt Architecture Authoring defensive system prompts with explicit boundaries and adversarial injection defense.
- Strict JSON Schema Enforcement Constraining completions strictly to validated JSON structures using native API function definitions.
- Automated Evaluation Pipelines (LLM-as-a-Judge) Writing automated test suites to score candidate prompt outputs against reference benchmarks.
- Prompt Regression Testing Detecting degradation in output quality across model updates and prompt refactors.
- Token Budget Optimization Trimming prompt verbosity without degrading reasoning performance to slash API expenditure.
Qualifications you will acquire
- Enterprise System Prompt Engineering Mastery: Demonstrated capability to author bulletproof system prompts for commercial software.
- Automated Prompt Evaluation Competency: Proven ability to deploy LLM-as-a-judge benchmarking suites for objective output scoring.
- Structured Data Extraction Qualification: Competence in generating schema-validated data ready for direct database ingestion.
Key features
- Hands-on Benchmark Construction: Build a functional prompt evaluation harness live during the session.
- Adversarial Prompt Hardening: Subject your system prompts to simulated prompt injection and jailbreak attacks.
- Turnkey Starter Evaluation Suite: Walk away with Python or Node.js scripts for automated prompt regression testing.
