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Drew's avatar

Great post, but two parts of your advice feel a bit stuck in 2025.

#1. Delegation Documentation can be written WITH the AI, not alone. E.g., Claude Code has a tool called AskUserQuestionTool that will interview you with multiple choice questions for as long as you want to build your Delegation Documentation for you.

#2. "Evaluate and review" should also be initially done by the AI, since effort is now free. You can prompt BOTH the task and its evaluation, and Claude Code can take on BOTH roles, going back and forth for you until the work product passes its OWN internal tests that it created as part of the task. When compute is free, AI iteration is free.

(Sample prompts of #1 and #2 are in the next comment.)

Asking humans to do these 2 steps outside of AI is just not necessary or efficient.

It's Sutton's Bitter Lesson. Don't be too clever; use more compute.

http://www.incompleteideas.net/IncIdeas/BitterLesson.html

Yes, this is a mind shift. Imagine growing up in a 3rd world country where clean water and electricity are scarce, and then you move to the US and have unlimited clean water and power. It will take you a while to stop conserving both.

The same is true for Knowledge Work Effort (KWE). We all grew up in a world where KWE was scarce, and now it's plentiful, and we're still out here trying to conserve. It takes some unlearning!

Consider teaching your MBA students: Stop trying to conserve effort.

Dov Jacobson's avatar

You assume that managers know what they want.

We think we know.

But I find that the acts of delegation and evaluation are precious opportunities to challenge and refine my initial plans. Whether with human or AI agents, explaining my idea often inspires rethinking it, and evaluating results always does.

Your model treats iterative delegation as mere inefficiency, overlooking its value as strategic refinement.

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