
Tool Use - AI Conversations The Blueprint For AI Agents That Work (ft Diamond Bishop)
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Jun 24, 2025 Join Diamond Bishop, the Director of Engineering and AI at Datadog, as he shares his expertise in building self-improving AI agents. He discusses strategies for establishing robust evaluation systems, fostering user trust, and choosing between prompt engineering and fine-tuning. Diamond also explores the balance of AI agents versus traditional scripts, the importance of dataset management, and the exciting future of ambient AI in DevSecOps. This conversation is packed with essential insights for anyone looking to create effective, adaptive AI systems.
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Weekly AI Updates with LM Notebook
- Diamond writes a weekly AI update newsletter using LM Notebook.
- This practice helps him stay informed and share curated insights internally and externally.
Manage Custom Prompt Risks
- Log user customizations and evaluate their impact using your eval suite.
- Provide guardrails or warnings if custom prompts negatively affect performance, but allow choices.
Synthetic Data to Address Imbalance
- Use synthetic data to augment rare or underrepresented cases in eval datasets.
- For more balanced datasets matching real use, production data alone may suffice.

