The Delegation Problem in an AI World

Fri, 12 Jun 2026 09:00:00 -0600

With the advantages of generative AI, some teams ship fast and present cleanly, then go quiet the moment someone pushes on the plan. It’s not because anyone is hiding something, but because the plan came from a prompt, and prompting your way around a hard decision is now easier than making one.

Most delegation advice says to evaluate what someone achieved, not how they achieved it. “State the destination and trust the route.” When delegating to an AI model, that gets a bit more challenging. Let’s dig into why and some questions you can ask to help you and your team better leverage these tools.

Evaluation on David R. Longnecker - Converting Coffee to Code

The Delegation Problem in an AI World