In November 2024, a Minnesota court filing highlighted the potential pitfalls of using large language models (LLMs) without thorough evaluation, as an affidavit supporting a law on deep fake technology contained non-existent citations fabricated by an LLM. This incident underscores the necessity of systematic benchmarking to ensure trust and reliability in AI applications, as reliance on vendor claims can obscure issues like cost overruns, latency, and compliance violations. A structured benchmarking framework involves defining success criteria, aligning tasks with evaluation metrics, choosing representative datasets, and establishing baselines. The framework emphasizes the importance of custom metrics for domain-specific evaluation, stress-testing edge cases, and continuous monitoring to adapt to evolving models and requirements. Galileo's evaluation platform is presented as a solution to streamline this process, offering automated evaluation environments, multi-model comparison dashboards, and continuous benchmarking integration to transform model selection from risky experimentation to data-driven decision-making.