Earlier quoted context omitted.
I feel like it's less about coming up with good ideas/questions and more about having the "idealized user." A user with extremely good taste that can guide development. And put that user in charge of everything.
How does the current Apple identify the correct idealised user when they don't seem to share the required taste? They need to relearn and engage in user discovery and questioning until they realise what niches they occupy and their use cases and needs. I doubt Apple's former lead would ever have put out a Mac that needs a dongle to connect to iPhone but not Android. I doubt he'd have killed Apple monitors as an iMac…
The original iPod was incompatible with many Macs still in use at the time that lacked FireWire ports.