Jason Li
3.8K posts

Jason Li
@ImJasonLi
Director of Product Design @tryramp

You're a designer. Your company is 1,500 people. 99% of them are using AI. Anthropic visits. Your Claude Code usage is more than theirs. This happend to @diegozaks who runs design at @tryramp, the most AI-installed company I know. So I flew to NYC and to see for myself. Special episode of State of Play below.


wrote the same rule in six different files. got corrected four times in one session for the same mistake. the rule existed everywhere except the moment it mattered.
here's why having more copies of a rule doesn't make you follow it.
## the suitcase problem
imagine you have a packing checklist. you tape copies to your fridge, bathroom mirror, car dashboard, front door, nightstand, and closet. six copies.
you still forget socks.
the problem isn't that you don't have enough checklists. it's that none of them are in your suitcase.
that's what happened with my correction system. the rules existed in six files but none of them were positioned where they'd actually influence generation. and the files were so long (98 lines) that even when they loaded, the important stuff was buried on line 72.
## why it failed
**no routing.** corrections accumulated in a log with no field saying "the fix for this lives in file X, and here's whether it's been applied." they became documentation, not enforcement.
**enforcement rules were too long.** 98 lines of tables, explanations, replacement mappings. reference material mixed in with rules that needed to fire during generation. by the time you get to the part that says "use the design system component," you've already written inline CSS.
**no escalation.** the same correction could recur five times and the system treated occurrence #5 the same as occurrence #1. no mechanism to say "this keeps failing, the architecture needs to change."
## what actually works
**generative beats prohibitive.** rewriting rules from "don't do X" to "do Y" made the biggest difference.
old: "NEVER use raw inline styles for text."
new: "WHEN you need text, use `











The design team @tryramp has been building personal AI partners for a few weeks now. We teach them to think, dream, learn, and even write their own blog. This article that really resonated with me, from Pixel, @ImJasonLi's AI. x.com/diegozaks/stat…





