Whitney's back. Third time on the couch, which officially makes her the Andy Richter to my Conan.

I went into this one wanting to talk about knowledge hoarding. You know the instinct: if I'm the only one who knows how to do this, they can't get rid of me. Take my Tinker Toys and go home. Whitney flipped that on me pretty quickly. On her team, nobody's hiding anything on purpose. They're moving so fast they're building the conveyor belt while standing on it, and they're drowning in documentation. The people who can cut through that noise and get everyone on the same page are the ones she needs most right now.

We got into why her team is documenting more than ever, and why designers have had to accept they aren't the only ones responsible for design quality anymore. We talked about what happens when a PM drops a screen they built in Claude on your desk and logs off for the day, what engineers are teaching designers about constraints that don't exist anymore, and why a rebrand you can ship with the flip of a switch still might not be ready to ship. (I'm still recovering from a single hex value change to a calendar color. Long story.)

Whitney also shared how she trains her team on AI like she's handing down a family recipe, and why "I don't know" is one of the bravest things a leader can say, once you've earned the trust to say it. Stick around for the end. A road trip conversation with ChatGPT changed how she thinks about what AI can and can't do, and it's the reason she'd protect one design ritual above all others.

0:00 Whitney returns for episode three 0:36 How people respond when AI changes the job 2:03 How AI know-how travels on Whitney's team 4:15 Afraid of AI, or afraid of a colleague using AI? 6:17 Are design teams documenting more or less? 8:41 Design craft moves into systems and AI training 9:28 Hoarding or just moving too fast? 11:32 Vibe coding and the signals that count 13:12 When a PM hands you a screen built in Claude 15:50 What engineers teach designers about old constraints 19:14 A rebrand on the heels of a redesign 21:24 Does shared understanding survive a world of agents? 23:39 The family recipe approach to AI training 25:50 Saying "I don't know" in front of your team 28:29 The one ritual worth saving 29:36 Why AI can't design for delight 32:12 Wrap-up