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.
This whole idea goes by the name Jobs to be Done. Intercom has a sick PDF book on applying the concepts to product development: https://www.intercom.com/books/jobs-to-be-done
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 sat next to a black LG is just so damn ugly. iOS, MacOS and current hardware shows, oh so clearly, that once notorious sense of detail and overall direction is long gone.
As is, their idealised user is envisioning all the wrong gimmicky things and missing most of the details. They're trying to play "what would Steve do?" but not being him they can't play that game well.
That just says it all really, doesn't it? Macs simply don't "just work" anymore. I feel like they're making almost random hardware changes
What's wrong with the USB-C to Lightning cable?
http://www.apple.com/uk/shop/product/MK0X2ZM/A/usb-c-to-ligh...
What type of user experience is that?
As a side note: there's nothing wrong with usb-c. I can see why it's an improvement! But the reason apple are pricks is they didn't also throw in a single usb-a port so we can keep using the dozen devices and 30 cables I already own.
It's one for people who pick up the new cable and get on with their lives.
One paper cut issue is solved by buying a cable and they can t get by with their lives on the new or lack their of new hardware.
The current phone does not come with a usb-c cable because it is older than the MacBook Pros and the Laptops don't come with a lightning cable because not everyone that has the laptop has an iPhone. I'm sure the next iPhone will come with a usb-c cable and then people will complain that they can't charge it with their old laptops.
The original iPod was incompatible with many Macs still in use at the time that lacked FireWire ports.