There’s a lot of news lately about Apple staffing up Siri. First we heard that they are adding something like 100 additional engineers to the product. Now the New Your Times is reporting Apple hired Google’s former artificial intelligence chief, John Gannandrea to oversee Apple’s machine learning and artificial intelligence efforts. Reportedly, Gannandrea will report directly to Tim Cook.

Speaking at John Gruber’s Daring Fireball party a few years ago, Apple’s Craig Federighi and Phil Schiller both explained that Apple can still make Siri smart without looking at all of its user’s data the way Google does. I don’t remember the exact example, but they said something like they don’t need to look at your pictures of mountains to teach a computer what a mountain looks like. Nevertheless, Siri does lag behind competing virtual assistants. I found their confidence uplifting because I want both to protect my privacy and for Siri to get smarter.

It looks like Apple is going to try and make Siri better by increasing engineering while maintaining its position on user privacy. I hope this makes a difference because Google and Amazon certainly aren’t standing still. 

Regardless, don’t expect results immediately. I think Siri improvements will be a gradual thing, over time. I think it’s similar to the way Apple has improved its cloud services. They’ve come a long way with iCloud over the past few years, but that would be easy to miss if you weren’t paying attention.

Yesterday Wired magazine published an article about the most recent improvements to Siri. Several prominent Apple executives participated including Alex Acero, the Siri lead, and Greg Joswiak.

The focus of the article was the improvement to Siri’s voice with IOS 11. Having used the beta now for several months, I can tell you that Siri is most certainly more expressive than in prior versions. The technology behind it, as explained in the article, is quite fascinating. Rather than using recorded words, they are using phonemes, which are the individual sound components of words assembled by Siri on-the-fly to be as expressive as possible.

One issue I would take with the article is that it almost feels as if they are implying Apple is only working on making Siri more expressive and not generally smarter. I’m pretty sure Apple can walk and chew gum, and from my own experience with Siri, it has continually improved since first released.

An example of this is calendar appointments. Up until about a year ago, scheduling calendar appointments was a syntax-heavy task with Siri. That’s not true anymore. Now there are several ways that you can naturally ask Siri to schedule an appointment, and she usually gets it right. The “usually” in that sentence is the problem. “Usually” needs to become “Always” or “Almost Always”. For Siri, the make-or-break moment is the first time a user tries to do something new. If you try to set a calendar appointment and Siri crashes and burns, you probably won’t try it again. To get more users to buy in, Apple needs to continue to improve that first experience, so users are encouraged to dig deeper.

The Wired article also addresses the different philosophies of Apple versus Amazon with the development of intelligent assistants. Amazon, with the Echo, is opening things for third-party developers making the device work with more services but also requiring users to learn the specific syntax needed to use those newly acquired skills. Apple, on the other hand, wants things to become more natural language-based where users don’t have to use a specific syntax to get work done.

For non-nerd users, natural language seems the only approach. I can’t imagine convincing my wife to memorize the appropriate speaking syntax for every service she wants to use through Siri or Alexa.

I think in the short term, the Amazon approach is easier and gets the ball forward faster. In the long-term, I think the Apple approach could be right if properly executed. If Siri does incorporate machine learning and artificial intelligence the way Apple wants it to, it could ultimately end up leapfrogging the syntax driven approach of its competitors. 

alt Mossberg wrote an article over at Recode, Why does Siri seem so Dumb?. In it Walt points out several failings.

I understand that Apple has fixed several of these issues since the article posted but that’s actually part of the problem. Why does it take an article by a popular journalist to get these things fixed? I feel as if Siri needs more attention. I don’t think the underlying technology is as bad as most people think but it is these little failures that causes everyone to lose faith. Siri is a cloud based service and needs to be upgraded and improved every day. While things are better, the rate of improvement needs to accelerate.

In our recent Mac Power Users episode on macOS Sierra, both Katie and I bemoaned the fact that you can’t verbally trigger Siri on the Mac. It seems a no brainer to me as someone with an iMac on my desk sitting there waiting to work 24/7. Several listeners wrote in to explain that you can trigger Siri on the Mac with your voice using the Mac’s accessibility features. Lifehacker has an article showing you every step to enable voice-activated Siri on your Mac. Click on the link to set it up but I will tell you that this actually involves making two separate voice commands: “Hello” and “Computer”. Having used it now a few days, I find it works best if you leave a slight delay between the two words. Have fun.

Siri’s original developers, Dag Kittlaus and Adam Cheyer, left Apple in 2011 and took a bunch of their team with them. Since then, they’ve been working on a new artificial intelligence system, Viv, that is going to get it’s first public demonstration Monday.

Right now there is a lot going on in the intelligent digital assistant world. While Apple was early to this game, Microsoft and Google are right behind and it’s clear there’s a lot of resources from a lot of big companies being thrown at this problem.

Most surprising to me has been the utility of the Amazon Echo. I have been using Siri for years but nobody else in my family does. I think it has something to do with the slight delay that exists between activating Siri and stating a command combined with the sometimes indecipherable syntax you need to use in order to make it work. There is also that thing where Siri will perform a complicated instruction perfectly only to botch things up entirely when you ask it to tell you the weather five minutes later. All of this has improved over the years but there still is enough resistance that my non-nerd family members are not interested.

The Amazon Echo on the other hand has no such resistance. I frequently witness my family turning on the lights, checking the weather, and otherwise interacting with Alexa. To me this is the closest glimpse we’ve had yet to a future with reliable intelligent digital assistants.

I’ve been thinking quite a bit about why the Amazon Echo is “stickier” for the non-techies in my house than Siri. One argument is because the Echo is always on and listening (which is kind of creepy). You don’t need to push a button to get it started. I’m sure that’s part of it, but I believe the real reason is because it’s both easier to talk to and more responsive.

Amazon’s Echo does a better job of parsing the question and giving you useful information. Too often, Siri gets confused because you don’t ask the question just right. Also, the Amazon Echo has never done that thing where it seems to understand me perfectly only report it can’t answer my question because of some mysterious problem out there on the Internet … somewhere. Either way, in the Sparks household the Amazon Echo has been a clear winner for my wife and children.

So getting back to where I started with all of this, we’re getting our first demonstration of Viv on Monday. Your guess is as good as mine over what the long game is for Viv’s developers. Maybe they want to wow us so some big company throws large sums of money at them. However, they already did that with Siri.

I suspect they are more interested in making something that they can develop without the limitations that come with tying their wagon to a large corporation. Keeping Viv independent allows them to make deals easier with third parties so it’s easier to add functionality. It also lets the developers be, generally, more nimble. The downside is that it’s going to be harder to activate. One of the big attractions of Siri is that it is everywhere on iOS. If I have to go open an application to get a digital assistant working for me, I’m much less likely to use it. (I downloaded Microsoft’s Cortana app and I still only launch it for the purpose of testing Cortana.) I think members of my family would be even less likely to launch an app for a digital assistant.

Either way, I hope that Viv is a smashing success. I want there to be a lot of competition in this space and I want these big companies to duke it out. It feels like we are on the cusp of having useful digital assistants in our lives and the sooner that comes, the better.

This week, John Gruber wrote a post about how Siri is becoming more useful to him. I think John’s right, Siri is a lot better. Although I am definitely looking at this from the vantage point of a Siri fanboy. I liked it from the beginning. I dictate often and like to think I’m pretty good at it. I’m actually dictating these words right now in Drafts on my iPhone. I’ve watched Siri grow up to a certain extent. Those people who gave up on it at the beginning are missing out. You should understand that like some other Apple terms (iCloud, for instance), Siri has several components.

Siri Dictation

This is the easiest bit. You speak and Siri returns your words as text. With iOS 8, Siri dictation got the ability to return your words as (or very shortly after) you say them. This was the single biggest improvement to Siri yet. With pre-iOS 8 Siri, you’d dictate your words and, only after you finished, would the recording grind through Apple’s servers and return words, at least theoretically. Sometimes it would just blink and silently mock you. Even if you have no interest in asking Siri how to bury a dead body, tapping the little microphone button and speaking to your iOS device (or Mac) to make words appear can be liberating. I recommend trying it for three days. It’s a game changer.

Siri the Intelligent Assistant

Then there is the entirely separate Siri that you ask to do something, like set a timer. This version of Siri has two jobs: 1) figure out what you just said, and; 2) figure out what you want it to do. Even if Siri gets all the words right in step 1, it still has a new and unique opportunity to fail in step 2. I think Siri has improved at phase 2 as much as it has improved at phase 1. I also think this improvement could only have come from Apple shipping Siri and letting millions of people bang up against it. While Siri is hardly perfect, it is damn useful.

Siri on the Mac

Apple has put dictation on the Mac with recent version of the Mac OS. It is, in some ways superior than Siri dictation in iOS, in that it no longer requires an Internet connection, assuming you enable enhanced dictation. However, Apple has yet to bring the Intelligent Assistant to the Mac. Dan Moren thinks they should and I agree. As someone who spends a lot of time behind a Mac, I’d love to be able to ask about the weather, set a timer, or do a simple web search with my voice. As Home Kit gets legs, it’d push more than few of my buttons to also be able to turn down the lights are start a playlist with my voice. I particularly agree with Dan’s desire for hypothetical Mac Siri to let users set the custom trigger phrase. Using “Hey Siri” leads to way too many hijinks as it is. If instead I could set my own unique phrase, I could make it something less likely to go off unexpectedly. For those of us that give our Macs names, it would also let us have a little fun. “Good Day Thelonious, What’s the weather going to be tomorrow?”