Humans, you may have noticed, are not exactly rational. And yet here we are, trying to get them to build software. It’s a bit of a mess. But there is some good news: by drawing on modern theories of human cognition we can begin to optimize our tools for how people think, not how computers work. I’ll talk about our experience at Yammer building human-centric tools for engineers, lay out the sociotechnical challenges facing organizations trying to build transparent architectures, and mention in passing how all of this relates to making money.