I'm the GC building an AI-powered legal function at Worksome and I’m documenting everything.
Some afternoons my brain is done with substantive work, but I still want the satisfaction of fixing something. So I stopped fighting it and started pointing that energy at operational friction instead. This time it turned a six-month vendor agreement I couldn't stand to redline into an actual skill I'll use for the rest of my career. Skill file download included.
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 grew up watching Silicon Valley build things because they could, then figure out the consequences later, or not at all. That's the lens I bring to AI now. Not fear, a method. Here's how I actually stress-test what AI tells me, including the skill I built to do it automatically.