Apple shuffles AI executive ranks in bid to turn around Siri

This is a big company problem. When companies grow, they eschew the folks who helped build it from the ground up and are intimately familiar with the business, products and customers in favor of people who have "worked at big companies". But in most cases, they didn't actually build them. So all they have to offer is the "big company baggage" that they were exposed to previously.

You can imagine how it usually works out ... after a few years of zero or negative progress, they'll move on to somewhere else, claiming victory on their LinkedIn profiles. Meanwhile the employees who actually built the company continue to get passed over in favor of another round of impostors.

So actually, staying at the same company for a long time probably means you're trapped by a glass ceiling and not promoted very far as you'll "never have had the big company experience that we need". Meanwhile, the company starts to stagnate.

/rant

The biggest thing that Ahrendts did was merge the online and physical stores. People forget that before she came around there was very little overlap. If you bought something online and you wanted to return it you had to ship it back instead of going to a store. It was one of the things that Cook wanted to get done by retail.

Katie Cotton’s departure was in no doubt at least partly to do with her health. She died not too long after leaving Apple.

It also isn’t clear to me how much Phil Schiller was “sidelined” vs him just wanting to retire.

To be fair, I’d counter with Jobs picking Jony Ive. Ive made gorgeous, lustworthy art objects that sucked as computers. The nadirs for me were iPhone 6’s bendgate and the 2015 MBP. Damn the functionality, we’ll make these suckers so slim you can shave with them! No one was begging for a MBP so thin it had to have compromised keyboard switches. Also consider the mouse that couldn’t charge while you use it, and the trashcan Mac Pro.

Those devices looked beautiful but they weren’t good at actually being used. Jobs let Ive design for a museum, not for the people using his creations. Cook let that continue for a while but finally reined it in and gave us useful designs again.

Which isn’t to say that Cook hasn’t made or isn’t making mistakes. I just meant that as a reminder that it wasn’t all wine and roses under Jobs.

Going to hard disagree with most of this. At any giant company with tons of executives (the article talks about the "Top 100" alone), if you didn't have at least some misfires then it probably means you're being too conservative. If anything, I give Apple props for making management changes relatively quickly when things aren't working out.

For example, I have the exact opposite view of the forcing out of Scott Forstall, which after reading what I think are fairly accurate descriptions of what went down was absolutely the right thing to do IMO. Forstall refused to own up to failures under his watch, which is an absolutely toxic trait in leadership (side note, when you're at that level it doesn't matter if the failure was "your fault", you still need to take responsibility for what happened, identify the root cause and make changes to reduce the possibility of it happening in the future). I am not an iPhone user, but every time the issue of Apple Maps comes ups, people say they love using it and that it's improved leaps and bounds over the years since Forstall was forced out.

> Promote Craig Federighi, after all these years I am still not convinced he is the right person for the job

Yeah I wonder about Federighi. He doesn't seem to catch much criticism from the Apple pundits—I assume because he's one of the few SVPs that seems like a real human in interviews and videos and not a stilted robot like the rest of them. But Apple's software, and macOS in particular, seems to be rotting from the inside out. Changes ship and everyone says "boy this is a step backwards, I hope they iterate quickly" and then it sits, almost entirely unchanged, for years on end. e.g. new Settings in macOS, Stage Manager on the iPad.

With how much the hardware team has been knocking it out of the park since the ARM transition it's really starting to feel like the software is the weak link. This rumoured massive redesign this year has me feeling very anxious.

> Putting too much trust on Eddy Cue

I've never understood the love for Eddy Cue. Apple pundits all seem to love him. Personally, I am really unimpressed by everything he's done. My understanding is he's been really good at negotiating big contracts.

I just don't think his execution or vision are exciting and, as you are hinting at, I don't think his moral compass points in the right direction. That said, despite some early pushback, my understanding is that Schiller was ultimately on-board with holding to the 30% cut.

This is a fantastic comment, I wholeheartedly agree with your assessment on Angela Ahrendts. What was once a magical experience going to a apple store has devolved into a nightmare. A few reasons why:

- The complete removal of spontaneity of the shopping experience. You wander over to look at a laptop and decide you want to buy it. Asking a employee is disagreeable as most have a ear bud in their ear receiving instructions or messages from who knows what, they hurriedly ask if you made an appointment or placed the order online and then rush away and sometimes return.

- Such a heavy emphasis on online booking for every conceivable issue. If you want a genius bar appointment you are angrily told you need an appointment and such an appointment is only available days or weeks away and at a inconvenient time for someone with a 9-5 schedule(Tuesday at 2pm work?).

- Last years accessories are gone. Try finding a iphone case that was made for a phone you bough 7 months ago and an employee looks at you like you are trying to buy a model T - (Wait you are looking for a iphone 15 case, wow thats a really old model, I don't think we have anything for that anymore).

- Insane levels of crowds, I can't think of the last time I saw a apple store open in the past 6-7 years that didn't have crowds inside the store like disneyland with service dogs, screaming kids and grumpy boomers yelling about how to transfer their grandkids photos from a phone to computer, just a terrible experience to deal with.

I bought the first iphone in 2007 and have had a model for almost every two years and have been going to the apple stores since then, and the past few years have seen a huge drop in customer experience due to alot of the issuses I listed above.

Probably an agreeability thing? The iconoclasts who get things done tend to be disagreeable, but success at a reality scale is different than success in a large company.

You get promoted and go up because of your peer coworker group's support, which creates a strong incentive to not rock the boat and go against sacred cows that work well enough. The person who succeeds in big company post a hypergrowth phase is a very different person than one who made the hypergrowth happen.

You mean the whole local-maxima problem?

> Is there an example, at a very large company, of an individual who “failed up” actually creating a hit in their next act?

If someone is successful their past is viewed differently. I doubt you’d “failed up” success stories because anyone who had great success would have their previous failures lost to history.

The key ingredients here appear to be audacity and persistence, with competence taking somewhat of a backseat.

This isn't intended to be overly critical. It aligns with the old adage, "If you want it, ask for it."

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Wait, are you saying there was a deeper meaning to S5E14 of Big Bang Theory "The Beta Test Initiation"? That would be quite hilarious.

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> They addressed this once with a huge “0 new features” iteration with Snow Leopard to catch up on the worst of it

This is a myth, though a myth created by Apple itself and Bertrand Serlet's tongue-in-cheek keynote slide. Snow Leopard actually had a number of new features: https://en.wikipedia.org/wiki/Mac_OS_X_Snow_Leopard#New_or_c...

Moreover, Mac OS X 10.6.0 was much buggier than its immediately predecessor Mac OS X 10.5.8. There were some really bad bugs in those early Snow Leopard releases.

The Snow Leopard that everyone remembers and loves was not version 10.6.0 but rather version 10.6.8 v1.1, which was released almost two years after 10.6.0.

Major OS updates invariably introduce more bugs than they fix. That's an iron law of software development. What Apple used to do, which they no longer do, is spend a long amount of time just fixing bugs in minor updates to the operating system. Now, unfortunately, Apple is on a rigid yearly OS update schedule. Worse, Apple doesn't just fix bugs between those yearly updates; instead they keep introducing new features even in the "minor" updates. So we never get a "stable" version. It's constant change for the sake of change.

Imagine that the last Major OS release was going to be a bug fix release ... but then AI happened. And imagine this happens every year with some new feature demanding it be shipped.

Having said that, here's the reality of bugs that are assigned to a team. Feature work comes first. The (older) engineers don't want this — they want to fix bugs, refactor code, get rid of tech debt. But ever since Jobs returned to Apple, it's become top-down and the engineers are no longer driving the ship. Management want the features.

So, the slippery part is this: once you defer a bug for an OS release and ship your product, deferring that bug in the next OS is a no-brainer. You already shipped with the bug, why is it so important this time around? So users/devs learn to work around the bug.

Occasionally, as an old-timer, I would on a whim just fix an arbitrary bug that was "bugging" me. Sadly though, the process had become so top-down though that I would also need: 1) someone to code-review the changes (and so already you are encountering your first obstacle requiring "buy in") and then 2) get permission from "management" (this might be the BRB, bug review board) in order to submit the fix and the Radar. (There are periods though when they are lax and bugs can be submitted with little justification — or we would just make up some bullshit to get the bug fix in).

I recall the early days with fondness when a dev just checked fixes in.

Me: Craig, are you working on the Crop tool in Photos?

Craig: Yeah, why?

Me: How does it pick the default for whether to use Portrait or Landscape? Half the time I think the default it picks is wrong. Why not look at the image bounds and default to Landscape if it is wider than it is tall?

Craig: Good idea. I'll make the change now and write a Radar for it later.

Also, a shout out to Brendan who would push back when in a feature meeting with something like, "Okay, which of these features can we drop? Because we have some serious technical debt we need to address that was not own your feature list."

Framing Snow Leopard as a "bugfix release" didn't happen for enlightened reasons, it happened because they cannibalized the Mac OS team and sent everyone to work on iPhone. The skeleton crew left behind lost the capacity to do anything but bugfixes.

This is why Snow Leopard was so buggy on release but unlike previous releases actually did get better: management stopped pushing new features, and even a skeleton crew was able to polish it over time. If you look at a map of tentpole Mac OS features, you can see that the ambition vanished with the iPhone's release and didn't recover for a decade.

I have no idea how Apple prioritise their bug fixing, but it really looks to me like bugs only get fixed when adding new features, if at all.

This is such a trivial big win as well, create a software dev team to focus on the outstanding bugs. Head it with one or two senior developers, make it the first step in onboarding new developers. What a great way to learn, and make a difference.

This is not rocket surgery, and Apple really do have a bad reputation here, even with the muggles.

They aren't even doing hardware well in some cases, their bread and butter.

Bluetooth has been broken on both editions of their Pro Max Phone (15 & 16). It cuts out and has all kinds of weird issues, but no fix has come for years now. This was why I always paid a premium for their phones, they did hardware and software well. Not anymore, their so focus has been on their processors.

Amen to that. Please for the love of all things remember your future defining ‘human design’ with brilliant UX in early macos and hypercard. Now you have unlimited money and don’t give a single f?

Do better please! Where is the passion, catering to pro’s, any idealism? Hardware is great but software gets worse and worse..

I was hoping for more from the new Siri, but its just awful for me. Latest example:

My wife and I were watching Jeopardy late at night, and Pol Pot came up. I asked Siri something like "Siri, tell me about Pol Pot" and instead, it heard "Siri, Call Scott", and rang my friend at 1am.

I’m one of them. I saw demos at _last year’s_ WWDC that I’ve been excited to get. And now with this announcement I don’t think that will happen before this year’s event.

I might be completely wrong, but by making “pro-privacy bets”, they shot themselves in the foot. Average customer ended up really not caring about the benefits that we try to promote, which hinders the development and features in some sense. Also, it’s still a pain for them to integrate AI in their second biggest market — China.

> Even just the most basic LLM integration, without even giving that LLM any personal data would be a massive improvement.

I don't think Apple will ever use LLMs, given the offensive output they can generate sometimes. There is just no way to make them safe for all audiences.

They're very good at marketing, I'm beginning to believe that's all they're doing well these days.

As an Android user I have to disagree, at least if we're comparing apples to apples (could not resist the pun).

Google Assistant with Gemini (or whatever its name is this month) is really remarkable at helping with mundane tasks, and I would really miss it if it were gone. Circle to search, asking questions about my agenda, and setting up new events on my calendar based simply on taking photos of documents or posters is so convenient that I really buy the concept of having an AI personal assistant.

And because this is a very sticky feature when delivered properly, if Apple is not involved it gives a very strong competitive advantage to Android flagships.

My life would rapidly fall apart.

I use Siri for about three things: timers, reminders, and asking about the weather. But the reminders are mission critical. I use the watch, and any time my flighty brain hits on something, I set a reminder for it on the spot.

I literally couldn't get along without it. The only killer feature of Siri is accurate voice transcription, and that's all I need (and it could be more accurate, I just get used to comical translations when I use a rare word).

I guess I wouldn't mind if it were better, but I don't need it to be. Reminders are enough.

The fact Apple Music has notifications advertising it on my lock screen, or splash screens advertising it once a month when I open Music.app would have been unthinkable pre-Tim Cook.

This is also one of my only uses of Siri, and the only one it gets right the large majority of the time. I also try to use it to se reminders in the future, but it’s a crapshoot whether it will get the date and/or reminder text correct.

I may be remembering incorrectly, but I honestly think it was better when it was released years ago than it is today.

My favorite is asking it to set a timer for n minutes, seeing the timer start and assuming it’s good, and only later realizing that it actually started a timer for n hours or n days. Learned that lesson with some burnt cookies.

Especially embarrassing when OpenAI's Advanced Voice can easily understand mixed-language contemporary slang on arbitrary topics, and even convincingly simulate it in the output. It can also do this at any volume, with "uhs" and "ahs", interruptions, corrections, and ignoring the accent.

Probably there's more, but expectations are so low that I don't even want to try.

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1) This appears to be what Apple has concluded by the action they're taking and implied by the premise of the article, versus my personal opinion.

2) The examples given may have been produced by AI/ML-based technologies developed at Apple, but may not have been the work of Apple's AI/ML Organization. Many "groups" (divisions) within Apple have their own teams using AI/Machine Learning (e.g. AI/ML Org coexisting with AI/machine-learning work and teams in TDG/VPG, SPG (special projects group: the one previously working on a car), etc.

More than that, they needed a professional with vision.

Given the size of Apple and these orgs, plausible. Siri also had a bunch of folks that came in from outside, through acquisitions, and did their own thing or tried to identify themselves and their roles as something different from Apple norms.

Apple had teams involved with AI/ML in several divisions also, from AI/ML (including Siri), TDG/VPG, SPG...

I suspect the most significant thing holding Apple back in the realm of AI is the fact that Apple prides itself as a company that delivers revolutionary products with ‘wow factor’ that is leagues above the competition. Apple just doesn’t have anything like that with AI.

Furthermore, the challenge with AI is that even though it can deliver some shockingly impressive results, it also generates some bafflingly stupid responses, as well as answers that are seemingly correct but are never less wrong in ways that are hard to determine. Those hallucinations really shatter the illusion of quality and reliability, which ultimately undermines confidence in the functionality as a whole.

Given that, Apple is stuck trying to catch up to the rest of the products in the AI space while also realizing that everyday AI is nowhere near as polished as Apple would expect it to be. So the more Apple pushes AI, the more customers are likely to pick up on the errors and inadequacies of the product.

Even though other AI assistants suffer from the same fundamental problems, the ones from Apple Intelligence are going to seem more embarrassing because of Apple’s brand image.

The devil is in the details – you do shit clippy-like integration = nobody will use it, you do it well – everybody will, even though nobody currently does in any meaningful way beyond setting a timer.

Well, the current iteration of Apple intelligence doesn’t enable personal context or 3rd party app related features at all. (https://www.macrumors.com/2025/03/07/apple-intelligence-siri...) So who knows whether people people want it or not; it’s not even out in the world! What Apple has actually discovered is that this is a hard problem to solve. But people do want a smarter Siri; they complain about it constantly.

Could Apple Maps on WearOS work as well as Google Maps, or does Google Maps there get special integration with something like Google Play Services?

WearOS in general seems to be much more restricted than Android with things like sideloading and restricting third-party stores, but I don't know if there are also things like the Google Play Services system privileges of google-Android proper.

I was a defender of Google Maps last week. Then I had to drive some roads I was unfamiliar with at the weekend to get to a familiar funeral.

Google Maps gave me instructions to turn off a junction right at the turn off, resulting in me missing it. Worst still, it did this not once but twice. And the detour was via road works.

Google Maps added a considerable amount of time onto what was already a 3 hour journey.

Thankfully I had planned for problems so there wasn’t any negative outcomes aside time lost and a considerable amount of additional stress when I was already in an emotionally bad place.

On the journey home I used Apple Maps and the difference in the directions were night and day.

Apple Maps gave me ample warning before each junction. It described the junctions (eg “right turn 100 yards after the traffic lights”) so I knew exactly where I was going. Even told me what lane I needed to be in.

Google Maps did do this on occasions to be fair. But it was highly inconsistent. Hence why I got stung so badly when its instructions were last minute. Whereas Apple Maps was 100% reliable 100% of the time.

It will be a long time before I rely on Google Maps for satnav again.

My wife doesn't have that problem with Google Maps on her iPhone, so I'm aware of that counter-point. It might have something to do with that I use offline maps. Things started breaking -- points of interest doesn't load, or maps freezes, etc. I have not been able to unbork it. And it had been noticeably getting worse.

But even when it had been working, I had started noticing navigation errors started creeping in. It was nice that I hear things like, "at the next McDonald's, turn left" ... but I also get other strange navigational errors. Even just last year, my wife and I hear the directions, and it is having us go in a confused way. I don't trust it as much. (And there is a lot I can say about this using Promise Theory to analyze all of this).

Last night, at a town I do not reside in, I'm making an errand to got to the grocery store, and Google Maps breaks again. So I use Apple Maps. Apple Maps navigation tells me to turn in, and that I am in the parking lot for my destination. I have never heard Google Maps doing that. Another time just last night, it told me that I am crossing this light, and to turn at the next light. I also never heard Google Maps tell me that. Those were literally the kinds of things I would ask my human navigator to tell me in addition to the standard Google Maps navigation (on my wife's phone).

I used to trust Google Maps, but in the last year it has given me some very bad directions that not only were wrong, but were sometimes dangerous. I've started to very much not trust its directions, which is unfortunate, because it used to be so great.

I've been an iPhone user for about ten years and have largely had the same relationship with Apple Maps for that time. Indeed, for the first time in a long time, I'm seriously considering switching back to Android later this year over a handful of annoying interop issues— chief among them the stuff recently surfaced by Pebble around APIs for wearables.

Not sure if that means I should try Apple Maps again at the 11th hour or not— maybe if it's finally gotten good it would be better to not know and just remain in blissful ignorance.

They spent more time polishing voices than they did on actual features, if anything, regressing them to the stone ages in terms of its primitive form.

Plus, there’s no more humor. Trying to crack jokes at it used to give funny responses. Even old things like “I need to hide a body” — “I don’t know how to respond to that”. Insult it and it’s a “I won’t respond to that”. Lots of old funnies are now gone and stripped away.

Siri wasn’t great but it was way, way more usable before the “machine learning” update whenever that was. Before it was a verbal command line, but at least you could learn some commands.

Now it’s a crapshoot.

All of them feel to me like they went backwards. In the beginning you could say you killed someone and it'd show you the nearest park/forest to bury them in. Now you can't even get them to play X on Spotify half the time.

That's also a nice explanation of why brain size among mammals scales with body size without necessarily leading to higher-order intelligence.

Woah!

You have no idea how much "hole" you just filled in my lexicon. Have been articulating this all wrong for years.

I was unaware of Apple’s military drone and missile programs. Could you point me to more information on those? I’m having trouble even imagining what an Apple drone would cost.

Having used it over the years I'm not. It feels like Siri uses AI/ML for speech recognition and then some pattern matching for the actual actions.

Meanwhile LLM's came along and shifted peoples expectations.

Mine told me the entire date instead of just the month.

He actually publicly did just this with the first iPhone. At introduction in January 2007 it had a plastic screen. He noticed the screen scratched easily in his pocket and they moved to a glass screen (and announced it) before it shipped in July.

> But the point of telling me the story anyways, which I think matches here, is he had a way of pattern matching the average persons expectations based in reality, and applying it to their technology, and then aligning people towards ambitious goals that were on some level based in reality (i.e. people use TVs, they are similar technology, people don't expect them to break).

Very well put!

I think you’re spot on here. What has been lost at Apple is Steve Jobs’ product mindset.

It's fine to explain why it is the way it is, but at the end of the day that's still just an engineering problem you need to try and solve. Sometimes Apple made mis-steps in that size/heat scenario but they've done it a hell of a lot better than anyone else for a long time. Sometimes you need demanding product types to force you to put serious effort into an engineering challenge you don't deem worthwhile.

There aren't a lot of phones that have air vents, except for the ones that also have fans. Convection doesn't work at those sizes and power levels. Thermal design for phones is all about conduction, getting the heat out to the surface of the device and spread evenly enough that there's no hotspot that would be uncomfortable for the user holding the device.

Also that the bubbles were visible to the rest of the room, or that the tiny amount of air was able to overcome surface tension in the first place.

Chekhov’s fish tank

As a pescatarian maybe he liked his snacks fresh XD

> there will always be some air unless you add extra filler. (and make everything run hotter)

Adding filler is how you make a passively-cooled device run cooler. Air that's not moving doesn't transport enough heat to be useful, and convection doesn't do anything in the narrow spaces between and above components on a circuit board. Thermal paste, graphite sheets, and vapor chambers are what phones these days do with volume that's not needed for circuitry or structural support.

I think you are imagining little tiny bubbles coming out.

Are more people using it more often driving up costs and there are pressure on some managers to reduce said costs?

As a user of all, Google Assistant and Alexa are miles ahead of Siri. Initially I just had Siri, and like you assumed they were all like that. Not the case. No more 'here's what I found on the web' or just not being able to help. Are they integral to my daily life, no, but definitely save time. Siri is just for timers and reminders for me.

Alexa sold 500 million devices. Before layoffs, they had 10K staff doing something. Their LLM product recently launched and is rolling out soon, lead by former head of MS Surface.

People keep talking in this thread about iOS / macOS being bug-ridden messes. I have to wonder if this is from users still on Intel chips.

My work MacBook with a now 3+ year old M1 Max? Rock solid. Rarely run into any problems at all. My iPhone? Also rock solid. Rarely run into any problems.

My Intel-based MacBook? Buggy mess. Like Apple has left the Intel side of the house to die on the roadside. As someone who still uses that at the time expensive device, I find this annoying. But I understand why they’re not investing resources into Intel bug fixing.

Maybe the problem is how the goal and objectives are set up which results in maligned incentives - "innovating" for the sake of innovation instead of fixing existing problem. The first results in nice power point presentations, the second doesn't.

Agree that they can't start from scratch. But they could acknowledge their shortcomings wrt to software and start moving things in the right direction. I had never seen so many complaints about software quality at Apple than the last release of MacOS with their networking issues and many other.

They are in a decent position where they already set expectations that they will deprecate and retire old stuff on a regular basis compared to Microsoft which is trying to preserve backwards compatibility forever.

Giving it to OpenAI won't solve their problem with Siri (although some of that expertise could help). Part of it has to be engineered into their platform with better extensibility while also preserving privacy, security, etc. And that work could also enable their platform APIs, Shortcuts and such to have access to a much more powerful set of things.