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In the end of his post absolutely eviscerating Apple for the bungled roll-out of Apple Intelligence, John Gruber cites an Adam Lashinsky report for Fortune where he gave a glimpse inside of Apple following another bungled roll-out: Apple’s first attempt at the cloud, MobileMe, back in 2008. It’s the perfect call-back here, so I can’t beat repeating it: Steve Jobs doesn’t tolerate duds. Shortly after the launch event, he summoned the MobileMe team, gathering them in the Town Hall auditorium in Building 4 of Apple’s campus, the venue the company uses for intimate product unveilings for journalists. According to a participant in the meeting, Jobs walked in, clad in his trademark black mock turtleneck and blue jeans, clasped his hands together, and asked a simple question:
“Can anyone tell me what MobileMe is supposed to do?” Having received a satisfactory answer, he continued, “So why the fuck doesn’t it do that?”
Somehow Jobs had managed to ask both a good, simple, and yet fundamental question, while also delivering a very clear message and rallying call. It was peak Jobs, totally in command of the ship. But more than that, he was the mast of Apple. If something wasn’t right, not only was he going to be the one to point it out, he was going to rip you a new sail. And if you were responsible, you were going to walk the plank. Now here we are, some 17 years later, and John Gruber is upset with himself: In the two decades I’ve been in this racket, I’ve never been angrier at myself for missing a story than I am about Apple’s announcement on Friday that the “more personalized Siri” features of Apple Intelligence, scheduled to appear between now and WWDC, would be delayed until “the coming year”.
I should have my head examined.
This announcement dropped as a surprise, and certainly took me by surprise to some extent, but it was all there from the start. I should have been pointing out red flags starting back at WWDC last year, and I am embarrassed and sorry that I didn’t see what should have been very clear to me from the start.
At the highest level, I was decidedly less surprised by this turn of events. In fact, I’ve been writing about it since the Apple Intelligence unveiling nearly a year ago. In a post entitled 'The Voice Assistant Who Cried Wolf', I made the case that Apple should in no way get the benefit of the doubt for these touted, yet unreleased new features because well, we’ve all had to live with Siri these past 13 years. If you'll allow me a lengthy excerpt from that post, as it underscores my point and plays well with Gruber's ultimate points: Compared to other AI events, it's all rather cautious. But that's exactly what it needs to be in order to garner mass usage. While others dance to the promise of technology that gives good demos, Apple waltzes in and productizes technology that can be useful today.
This level of restraint and practicality engenders trust in their products. And Apple's focus on privacy and security just doubles down on that trust. And that has arguably never been more important than it is right now with the tentacles of AI reaching out to touch everything in computing. That's the playbook. Rinse. Repeat.
Except wait. Hold on a minute. Back to the sink.
Watching the keynote again today I couldn't help but hear this voice in my head. A voice that sounded a lot like Siri. A voice telling me something completely useless in response to a simple query. Such has been the state of Apple's AI – OG AI, sure, but still AI – for over a decade now. And despite promise after promise that with this next update, everything would be better, Siri has broken our trust. Over and over and over again.
So you'll forgive me if I pause at the notion that yes, this time it will be different. It's certainly possible that the LLM revolution will change the equation for Siri. And/or that ChatGPT will fully fill in the many Siri holes. But I watch these demos and I'm still just beyond skeptical that it will all work as well as it seems to. That's true of basically all demos, of course. But why are we trusting Apple this time?
And that's a problem because Siri remains at the heart of what Apple is selling with the new intelligent future. I don't care how nice her new coat of UI paint looks, if we ask her about our mom's flight and she can't figure it out, or spits back bogus information, well, we're back to where we are right now. With Larry David screaming obscenities at his phone.
I would love for all this to work as advertised. But I also would have loved for it to work as advertised in 2011. And 2012. And 2013. And 2014. And 2015. And 2016. And 2017. And 2018. And 2019. And 2020. And 2021. And 2022. And 2023.
Every single year Apple promises that this will be the year that Siri is good. And every single year, she sucks. Sure, she perhaps sucks less at what she sucked at previously, but she sucks more overall because the state of the art and the expectations are now far greater. And never has that been more true than in our age of AI. And so did I believe that Apple was going to rise to meet the moment? With Siri? Again, you’d have to be crazy to believe that. And so while Apple gave impressive demos — on video — of what we could expect, I absolutely needed to see it, to believe it. I drove home this notion the following week, even evoking the dreaded "v" work in my title, 'With AI, is Apple Getting the Vapors?', writing: It also makes me continue to worry more than a little bit that we can't trust in all the upgrades we heard about with Siri, in particular. Because nearly everything demoed with the voice assistant in the keynote won't be coming until next year, says Gurman. So does Apple even know and trust in how well it works right now? Is this one of those, let's draw a line in the sand and hope that the continued improvements in AI over time get us there?
Narrator: it was. My own mistake was that I assumed I would see it and that it would still suck. I did not expect not to see it. That’s the surprise here to me. Apple touted vaporware on stage. To be clear and fair to them, it’s presumably better not to ship this element of Apple Intelligence if it’s not any good. But as Gruber points out, then the mistake was in touting it. Both “on stage” (on video) — twice — and in television commercials! Apple has now had to pull those videos. How embarrassing. I’ve already made the case that this is actually more than embarrassing, it's concerning about Apple’s long-term prospects with regard to AI. Because they clearly thought they could ship such features on time and on target. Some believe this change may be related to security. Because this is Apple’s AI — Siri — handling your very personal data stored on your devices, there’s a far greater risk than with more “general” AI services, the thinking goes. It’s possible, and I wouldn’t be surprised if Apple uses that as an excuse/rationale regardless, as it fits their overall narrative well. But I think it’s just as likely — if not more so — that such features simply don’t work. That Siri simply doesn’t work. Again. Mark Gurman’s sources pointed in this direction in his Bloomberg report on the matter: Bloomberg News reported on Feb. 14 that Apple was struggling to finish developing the features and the enhancements would be postponed until at least May — when iOS 18.5 is due to arrive. Since then, Apple engineers have been racing to fix a rash of bugs in the project. The work has been unsuccessful, according to people involved in the efforts, and they now believe the features won’t be released until next year at the earliest.
In the lead-up to the latest delay, software chief Craig Federighi and other executives voiced strong concerns internally that the features didn’t work properly — or as advertised — in their personal testing, said the people, who asked not to be identified discussing internal matters. An Apple spokeswoman declined to comment.
Some within Apple’s AI division believe that work on the features could be scrapped altogether, and that Apple may have to rebuild the functions from scratch. The capabilities would then be delayed until a next-generation Siri that Apple hopes to begin rolling out in 2026.
That isn’t Federighi saying they needed to push the features because of security, that’s him saying they needed to push them because they suck. Another “So why the fuck doesn’t it do that?” moment, perhaps delivered in a slightly less curt manner. But actually, that curtness may be exactly what Apple is missing here. A real fire lit underneath asses to fix the situation. Hopefully that’s happening. But part of the problem here is that it’s not clear who would be the one to deliver such a message. While it’s widely reported that Tim Cook can have a temper, in particular around underperformance or incompetence, the knock on him has long been that he lacks the product chops to perform the role that Jobs so critically filled for Apple. Said another way: it’s easy to imagine Cook getting pissed off if Apple misses a logistics-based timeline, because that’s his world. But it’s harder to imagine that he’d get super passionate around a product not being particularly perfect. All these years later — right or wrong — I’m just not sure that he can be trusted to make such judgements as Jobs could. To be clear, Cook has been an amazing steward of Apple. Probably the perfect one for this era of the company in many ways. And Apple becoming the most valuable company in the world for a large part of his tenure is testament to that. And I do believe he cares about what Apple does and ships — and I do believe him when he talks about the profound importance of Apple’s advances in products like the Apple Watch actually saving real human lives! But this situation around Apple Intelligence is different. It’s a new field and a new era, and I just don’t trust Apple here for the recent historical reasons mentioned. And nothing I’ve seen or heard in recent months leads me to believe otherwise. Yes, I was holding out hope that the innovations behind AI would start to slow enough that Apple could be the one to best productize such advances. But we’re not there yet. And so, in a weird way, it still feels as if Apple is too early in AI, at least for them. They clearly — clearly — felt pressured by Wall Street into rushing Apple Intelligence out the door. Cook can say he doesn't "consider the bloody ROI" all he wants, he obviously does at least somewhat! And he should! Apple is so big now — again, the most valuable company on Earth — that the stock is vital to a sizable part of the American economy. Apple can’t just sit back and see Microsoft soaring to new heights on the back of AI while they wait on the sidelines. I mean, they could — and perhaps should have done that in hindsight — but they would have been punished for it, by Wall Street. And that would have punished many a 401k. It’s a tricky situation. But setting that aside, I’ve been making the case for a while now that there are an increasing number of signs that Apple lacks that single signal caller. That “mast” to use my analogy above. Instead, Apple has seemingly been trying to emulate it through various lieutenants, almost all of whom date to the Jobs era of Apple, from Cook on down. Forgive me, but there may be too many Cooks in the kitchen. As I wrote last May: I worry that today's Apple is still living in the shadow of Jobs. It's hardly surprising given that he was both the founder and savior of the company. But it's likely exacerbated by the fact that most of the key core executives today are still from Jobs' era and lineage. Phil Schiller. Jeff Williams. Eddy Cue. Greg Joswiak. Sabih Khan. Johny Srouj. Deirdre O’Brien. Craig Federighi. Even the star of yesterday's show, the relative fresh-faced (in terms of being forward-facing – and clearly being set up for bigger things) John Ternus has been at Apple since 2001. And, of course, Tim Cook. That's 9 of the 12 executives who have been there since the Jobs era – a few of them there before Jobs came back!
To be clear, that's a strength in terms of continuity, experience, and institutional knowledge. But there are downsides. Especially under that shadow of one of the greatest entrepreneurs the world has ever known.
To his credit, Jobs famously told Cook, "Never ask what I would do. Just do what's right." I believe Cook believes he's doing this. But I also believe what Cook thinks is right is too often what Jobs thought was right before Jobs would change his mind and actually do what's right. And I think Schiller and several other executives have fallen victim to this as well.
But I also now worry that the wrong lesson may have been taken from that message – one which Jony Ive also brought up recently (admitting he fails to follow it). Apple started operating differently, without that single decision maker on everything, but collectively they were all perhaps sort of making decisions that they thought Jobs would have made. Because it was The Apple Way! And the company not only survived, but thrived post-Jobs. But that was mainly in making calls that were set in motion by Jobs — the more obvious decisions. It is these truly new vectors where Apple has now struggled. Vision Pro is one very tangible example of this, but Apple Intelligence is now a less tangible, but perhaps more problematic one. “A thousand ‘nos’ for every ‘yes’” probably should have been a thousand and one or two… Jobs, of course, wasn’t perfect. And he oversaw plenty of his own duds and failures. But as Gruber notes, perhaps the most important thing he did when he came back to Apple was to instill a sense of trust in their products. That the vast majority of the time when they shipped something, it was going to work and it was going to be great. It’s hard to overstate what a burden of choice this lifts off of consumers heads. It's an intangible thing that transfers – until it doesn't. Back when I was a tech reporter, I had a reputation for being an “Apple fanboy”. I never minded it because it was mostly true. I was a huge fan of Apple products because of the above. I did not start out that way — I was the kid who went to the midnight launch of Windows 95 for Chrissakes — but once I jumped ships, I was hooked by the attention to detail and per above, the inherit promise of quality with Apple products. In more recent years, I’ve gotten almost the opposite charge: being too hard on the company. For a while, people chalked this up to the fact that I went to work for Google. Never mind that I refused to use anything but Apple products during that entire decade-plus. And never mind the fact that I’m saying the same stuff now that I’m long gone from Google. My aim has always simply be to put my opinions out there and, ultimately, to be proven right in those viewpoints. And I’ve just been seeing an Apple that has been slipping for years now. And this situation is, in ways, a culmination of a thousand little things. A thousand yes’s that should have been no’s. Jobs once famously said that “it’s more fun to be a pirate than to join the Navy.” Remarkably, it was a sales pitch to join the Macintosh team within Apple, instead of staying underneath the bigger company. And so a part of me can’t help but feel that Apple these days is now just the Navy with nary a pirate to be seen. Mistakes are made due to bureaucracy and the fact that while a ship may have a captain, the Navy has all sorts of rank and file leaders to whom bucks stop. Maybe a nearly $3T company can’t possibly also house a band of pirates. But they should try! Going back to the Lashinsky article: For the next half-hour Jobs berated the group. “You’ve tarnished Apple’s reputation,” he told them. “You should hate each other for having let each other down.” The public humiliation particularly infuriated Jobs. Walt Mossberg, the influential Wall Street Journal gadget columnist, had panned MobileMe. “Mossberg, our friend, is no longer writing good things about us,” Jobs said. On the spot, Jobs named a new executive to run the group.
I’m glad John Gruber wrote his article because by many accounts, from the execs on down, he’s viewed in that sort of Mossberg sphere. And so hopefully someone internally is calling a town hall meeting right now and yelling that “Gruber, our friend, is no longer writing good things about us.” I just have no idea who is delivering that message.
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