The Sky's the limit: AI automation on Mac

Summary

I’ve been sitting on this draft for a few days now, partly because I thought it would turn down the bitterness, and partly because I kept asking myself whether I should even write it. But I think it is worth getting out of my system, so here goes. In case you’re not in the Mac community, Sky is an app that brings AI automation to the Mac that Federico Viticci wrote about at length last week, and that not only looks and feels exactly like what I would expect Apple Intelligence to be like, it also completely blows out of the water all the desktop automation tools that have sprung out of the MCP hype. I have several questions, some of which I have already sort of asked back in March, but which I think are worth reformulating. The people who created Sky are the same people who created Workflow and worked on Shortcuts, so here’s my first question: Why wasn’t Apple able to harness their expertise in the first place? I mean, people have free will and all, and can choose to work wherever they want, but this makes my earlier rant about their having neglected automation feel like the first clue to a corporate culture murder scene. Not having made it possible for them to thrive feels like vanilla corporate politics, but having brilliant people leave Apple and ship something that is, even in preview, much better than anything that Apple Intelligence promised (including the made up bits they paraded as marketing material) is just gross mismanagement (now you know why I held back on this draft). Which leads me to my second question: Why has Apple failed this badly? Was it just a consequence of their innately siloed nature? The internal decline of John Giannandrea’s team (and the rumored hand-over of Siri to Craig Federighi team) might have played a role, but macOS has been largely stagnant from a UX perspective for ages (and as far as I know it isn’t even being addressed in the upcoming Solarium redesign), so I have to assume the Sky team saw this huge blind spot in terms of impr...