AI can draft a contract playbook in an afternoon. Clean positions, clean fallback language, and reasoning that reads like it knows what it's talking about. But it doesn't. Back in 2014 it took me years of clause deviations and fights with finance to build a playbook that actually worked, because the reasoning behind it was documented. Here's what a modern playbook needs to look like, and why AI doing the legwork still needs you checking the reasoning before it goes live..

I had eight worker agreements, eight different outside counsel drafting styles, and a plan to fix all of it at once with AI: pull in the substantive revisions, reformat everything to match, and reorder every clause so IP rights lands in the same spot no matter which country you're looking at. Three jobs, one prompt, zero upfront plan. Here's exactly where it fell apart, including the moment I told AI to "just start over" and it decided to be even more helpful.

When product wanted to build a bot at our hackathon, I asked one question: How often does this come up? The answer changed their plans. Here's my five-question framework for deciding what's actually worth building and what decisions you need to make along the way.