Cook and modern Apple encounter delays from the standpoint of an unknown unknown. It's a surprise! They aren't realistic at the executive and project management levels so it catches them out- the car and AI are good examples. Jobs knew when delays were coming down the pipe because he was a cross-silo participant and intimately involved. As such he could craft the story and not let the press draft it for him. Whether people believed it is another discussion but he had intimate knowledge of all the areas at all or mostly all of the time.
Jobs was a tough guy with expectations too, but begrudgingly wanted something to be delayed rather than to suck. Before he left, Lisa III was probably his highest profile failure then. But he knew what came next and the risk was worth the delay. Maybe, the Pixar computer comes next? His constant drive to tirelessly iterate is lost on modern Apple and that's the secret sauce. Making the mistakes and failing before something hits the public.
But let's Look at public misses. Look to OS X 10.0. I installed it on a Power Mac G4 400. It sucked. Possibly the most potentially damaging and very public mistake. And an internal call to arms. This was to be the cornerstone for the next decade of their computers so the alarms sounded internally. They relentlessly drove to improve it. Year over year. 10.1 was miles ahead, moreso 10.2. They kept driving forward. That attitude and drive is missing with the Siri/AI team and modern Apple in general. Granted we are comparing an accountant/supply chain genius to a Renaissance man so there's the schism. But it's easy to see the lack of vision has led to unforced errors. Would Jobs have announced Siri and AI during WWDC only to announce a delay? Maybe but probably not. In his speeches in the early 80s he talked about the kinds of technology that were at their infancy but he saw those things as if they were mature. I think it could be said with confidence he would have pulled sharply towards AI a few years back, he might have delayed products and moved teams around to bring human capital to bear. It's a fascinating discussion if you have the frames of reference to measure it out. He would absolutely have delayed anything and everything in service of bringing Apple Intelligence into a category-leading position, everything else be damned.
