25. Designing Context for AI Systems [Paz Perez]

Search sends fewer people to your website every month, and the answer engines keep most of the ones it does send. Kevin Wong, VP of Design at Webflow, doesn't think that means the website is dead — he thinks it means the metric you have been judging it by is.

Most companies handed their people a powerful new machine and said "go do something with AI." Melissa M. Reeve, author of Hyperadaptive: Rewiring the Enterprise to Become AI-Native, argues that's the whole reason the returns haven't shown up — and the reason so many of us feel like we're sprinting to stay in place. Melissa has spent three decades inside organizational transformation, and her case is that AI is an organizational design problem rather than a tools problem. Brittany and Arpy get into what that means for the people living it: where the jobs actually go when work gets automated, why the career ladder is dissolving into something else, why she's genuinely bullish on UX, and what to do when it doesn't feel safe to raise your hand and ask to slow down.

Most companies are burning millions chasing an edge with AI and getting almost nothing back. Rebecca Hinds runs the Work AI Institute at Glean, and her research maps exactly what the small group of teams actually winning with AI do differently — and why everyone else stalls. In Glean's 2026 Work AI Index, 87% of workers said AI improves their work, but only 13% of their companies say they're actually performing better because of it. The winners closed that gap on purpose, and this episode is about how. We get brutally honest with Rebecca about our own experience — feeling like the AI's assistant, drowning in unreliable output, riding waves of excitement and dread — and she ties each one back to the data: what the leading teams do to turn individual speed into real organizational value, the 6.4 hours a week most workers lose to "botsitting," why context (not more tokens or MCP connections) is the real unlock, why domain expertise decides who actually benefits, and how the best organizations measure value without chasing vanity metrics.

Christian Crumlish watched Elon Musk's DOGE team take a buzzsaw to the federal government's own product organization — the teams he'd spent years helping build — and he has a specific, ungentle theory about what they got wrong and the surprising thing they may have gotten right. But the deeper thread of this conversation is what happens to the rest of us as agents absorb more of the work and the cost of shipping falls toward zero. Christian walks us through the real math of replacing people with agents — and the "reverse centaur" trap waiting on the other side of it — why some AI salaries have stopped tracking value entirely, and his own mid-career decision to trade a bigger paycheck for work he could still defend to himself. His argument is oddly hopeful. Your work still has meaning; it just might not live inside the industry or the company you built your career around. This is a conversation about reinventing your career in the age of agentic AI, from someone who has done it more than once. In this episode you'll learn: ➜ Christian Crumlish on what Elon Musk's DOGE team got wrong tearing through civic tech — and what it may have improved. ➜ The reverse unicorn: Cory Doctorow's term for when your AI agent keeps the fun work and hands you the boring parts. ➜ AI engineers and PMs pulling $1M+ comp — Christian argues that points to something more than value-based outcomes. ➜ Why the meaning in your work may not live inside the industry or business you built your career around anymore. ➜ Building a "Product OS" — skillifying the tacit product knowledge locked in one person's head.

Two years ago, Josh Clark and Veronika Kindred previewed a book about a coming era of sentient digital experiences on this show. That book, Sentient Design, is out now — and the future it predicted arrived faster than most companies' data, governance, or restraint could keep up with. We talk with them about why most "agentic" features are still just a chat sidebar bolted onto an old product, what a gym-booking AI agent's very bad week reveals about designing for agents instead of people, and why Google running the biggest sentient design experiment alive — its own AI Overviews — is already rewriting how businesses get found.