Norman Winarsky headed SRI’s entrepreneurial arm at the time of Siri’s development and acquisition, and was a co-founder and board member of the original Siri company. He expected that Siri's arrival on the iPhone 4S would be the start of another revolution.

However it didn't and part of the problem was that in seven years Apple could not make Siri any better.  She still stumbles over spoken requests and struggles to integrate the many things it should know about you into useful responses. While the Tame Apple Press insists that Siri is the "most popular AI" that is simply because Apple shoved it in a lot of gear and not because anyone likes it. In fact Siri use is falling.

Winarsky thought Siri would be much further on at this point and told Quartz Siri should be able to do more than setting reminders, checking the weather, sending texts for you and other relatively mundane tasks.

But it has an imperfect grasp of users’ preferences and past history. Its predictive intelligence is limited—it’s not great at knowing what you want before you know you want it. And while vastly improved from its earliest days, Siri cannot speak well with the users either.

Winarsky acknowledges that some of this disappointment stems from the sheer difficulty of predicting the pace of major technological advancement but it is also grinding to a halt because Jobs' Mob took Siri in a very different direction than the one its founders envisioned.

Pre-Apple Siri was intended to launch specifically as a travel and entertainment concierge. Were you to arrive at an airport to discover a cancelled flight, for example, Siri would already be searching for an alternate route home by the time you pulled your phone from your pocket—and if none was available, would have a hotel room ready to book. It would have a smaller remit, but it would learn it flawlessly, and then gradually extend to related areas.

Apple launched Siri as an assistant that can help you in all areas of your life, a bigger challenge that will inevitably take longer to perfect, Winarsky said. However competitors like Google Assistant have already surpassed Siri’s ability to navigate travel and other logistics.