John Giannandrea to Retire from Apple

In game design we used to call this opacity “hunt the verb” in text adventures.

All chat bots suffer this flaw.

GUIs solve it.

CLIs could be said to have it, but there is no invitation to guess, and no one pretends you don’t need the manual.

I get this pain with Apple in a bunch of different areas. The things they do well, they do better than anyone, but part of the design language is to never admit defeat so very few of the interfaces will ever show you an error message of any kind. The silent failure modes everywhere gets really frustrating.

I’m looking at you, Photos sync.

EDIT: just noticed this exact problem is on the front page in its own right (https://eclecticlight.co/2025/11/30/last-week-on-my-mac-losi...)

Ironically this manages to break all four of Apple's famous UI principles from Bruce Tognazzini: discoverability, transparency, feedback and recovery

Yeah, it's a classic CLI v GUI blunder. If you don't know exactly what the commands are, the interface is not going to be particularly usable.

I've found I appreciate having Siri for a few things, but it's not good enough to make it something I reach for frequently. Once burned, twice shy.

This is just the conversational interface issue. You need the system to be able to do most of the things you would expect a human to be able to do (e.g. if you're talking to your phone, you'd expect it to be able to do most phone things). If the conversational system can only do a small subset of those, then it just becomes a game of "discover the magical incantation that will be in the set of possibilities", and becomes an exercise in frustration.

This is why LLMs are the first conversational interface to actually have a chance of working, once you give them enough tools.

I didn’t know for years that you can ask it to do things remotely over SSH.

My favorite is when you have Siri off but CarPlay on. You can be actively navigating, but say “find me the nearest X” and it’ll say “I’m sorry, I don’t know where you are”

You would think it's the opposite. "I'll tell you where the gas station is because it's preferable to you looking at a screen in your death can"

Asking “what’s the weather” in the morning gets Siri to yell at you about the phone being locked, or even “I don’t know where you are”.

It’s such trash. Constant conditioning for garbage.

Timers and alarm clocks it is.

> voice simply isn't a great way to interact with computers in the general case

You know I have talked to chatGPT for maybe a 100 hours over the past 6 months. It gets my accent, it switches languages, it humors. It understands what I am saying even if it hallucinates once in a while.

If you can have chatGPT level of comprehension, you can do a lot with computers. Maybe not vim level of editing, but every single function in a driving car should be controllable by voice, and so could a lot of phone and computer functions.

It's great interface when your hands are doing something else so I do see the appeal.

Just that... nobody is willing to pay much for a thing that will do some basic search, dictate a recipe, or do unit conversion, or add a thing to a list.

Alexa has this annoying habit of being non-deterministic.

> Alexa, turn on the bedroom lights.

> OK lights turn on

In the evening:

> Alexa, turn on the bedroom lights.

> I'm sorry, I don't know a device called "bedroom lights".

How is it even possible to build a computer system that behaves like this?

Alexa has gotten significantly worse with the "Alexa+" AI updates. I used to be able to say stuff like "Alexa, set the lights to 5" and it would turn the lights to 5% in the room I was currently in. Now half the time it tries to start a conversation about the number 5, or the northern lights, or other random nonsense. Absolute garbage.

Siri could've done better but Apple is definitely taking big risks with their privacy play. They might just corner themselves.

Agreed. I often have to verbally battle with Siri to do the most basic interaction. Siri recognizes all my words but misinterprets my intent and does something I didn’t want.

It was driven by privacy and on device compute.

Anything you ask an Android device to do, or an Alexa device goes to their clouds to be 100% processed there.

Apple tried to make a small and focused interface that could do a limited set of things on device without going to the cloud to do it.

This was built around the idea of "Intents" and it only did the standard intents... and app developers were supposed to register and link into them.

https://developer.apple.com/documentation/intents

Some of the things didn't really get fleshed out, some are "oh, that's something in there?" (Restaurant reservations? Ride Booking?) and feels more like the half baked mysql interfaces in php.

However, as part of privacy - you can create a note (and dictate it) without a data connection with Siri. Your "start workout" command doesn't leave your device.

Part of that is privacy. Part of that is that Apple was trying to minimize its cloud spend (on GCP or AWS) by keeping as much of that activity on device. It wasn't entirely on device, but a lot more of it is than what Android is... and Alexa is a speaker and microphone hooked up to AWS.

This was ok, kind of meh, but ok pre-ChatGPT. With ChatGPT the expectations changed and the architecture that Apple had was not something that could pivot to meeting those expectations.

https://en.wikipedia.org/wiki/Apple_Intelligence

> Apple first implemented artificial intelligence features in its products with the release of Siri in the iPhone 4S in 2011.

> ...

> The rapid development of generative artificial intelligence and the release of ChatGPT in late 2022 reportedly blindsided Apple executives and forced the company to refocus its efforts on AI.

ChatGPT was as much a blindside to Apple as the iPhone was to Blackberry.

Yeah, I'm not buying that either/or framing too

They are solving for privacy before solving for the UX.

They should actually make something useful first, and then work backwards to making it private before releasing it.

Don't invert the argument, something can be enormously useful while also having an equally big effect on one's privacy.

You'd have to expand on that because I don't see why one is related to the other. People get value out of giving their data to OpenAI. They don't care. So what?

China does not care about personal privacy, they only care about privacy beyond their political boundaries.

If you've never been to China, you need to look no further than the streets to understand this (cameras everywhere, social credit system, etc.)

I agree that not falling for the hype and rushing in may have just saved them. Apple is typically not a first mover. They often hang back, rethink the problem, and deliver something really nice. But not in this case. They had Siri first and then squandered their lead, but may have avoided a huge write-down as a result.

That's a great point and an easy way to visualize it as an outsider, but it's not necessarily that simple.

For one thing, the iPad (market-leading tablet) and the iPhone (market-leading pocket touchscreen device) were not their first attempt at doing that. That would be the Newton, which was an actual launched product and a commercial failure.

For another thing, even Apple can't just become the market leader by doing nothing. They need to enter late with a good product, and having a good product takes R&D, which takes time. With MP3 players, smartphones, and tablets, they didn't exactly wait until the industry was burnt through before they came in with their offering; they were just later (with the successful product) than some other people who did it worse. They were still doing R&D during those years when they were "waiting."

Apple could still "show up late" to AI in a few more years or a decade, using their current toe-dipping to inform something better, and it would still fit into the picture you have of how they "should've done it." Not to mention, Apple's also lost its way before with things like convoluted product lines (a dozen models of everything) and experimental products (the Newton then, Apple Vision now); messing up for a while also isn't exactly bucking history.

Because today they're racing against regulators for the privilege of setting their own service as the preinstalled, exclusive, default with APIs only they are allowed to use.

They already lost this superpower in the EU and I think Japan, India, Brazil too. Early next year they've got their US antitrust trial, and later in the year are some class actions challenging their control over app distribution, and at least two pieces of draft legislation are circulating that would require allowing competing apps to be defaults.

If they need another two years they might face an entrenched and perhaps even better competitor, while their own app needs to be downloaded from the App Store.

MacOS (or whatever they're calling it now) for all its faults is still probably the best desktop OS for getting things done without having to fiddle around much. ChromeOS is close but still so far in many ways.

And for audio production - I'm just a dabbler, really, but I've been able to do some really impressive things with just GarageBand and a Fender Mustang Micro amp-plug over USB-C. It "just works" unlike my experience on Linux recently, where there are lots of little bits that are genius, but I couldn't manage to figure out how to get a basic midi synth working with a DAW that had a UI that was designed for humans. (Jack is amazing, though - being able to do arbitrary audio filter chains with random pieces of software is seriously cool.)

I don’t remember Windows 8 being particularly transparent. Windows 8 is remembered for the start screen with the modern tiles.

This sounds like you take slights toward Apple weirdly personally.

Not to mention all the useless LLM fluff Gemini has. I turned off Gemini because simple questions like "What's 1 USD in AUD" would be met with 30 seconds of "As a large language model, I can't provide investment advice, so it's always important to check information yourself [...], but one Australian dollar is approximately $0.65" (note the conversion in the wrong direction). By comparison, Google Assistant just gives you a number straight away.

I guess it depends on what you mean by voice assistant.

But Android has been 100% accurate for simple commands for over a decade for me. Things like:

- "weather." tells me forecast of where I am.

- "alarm at 8am" and "alarm in 30 minutes" works as expected.

- calendar commands also work

My favourite is "go home" which opens Google map with a route to home.

These things just work. I don't recall last time I had to repeat myself.

Exactly. Looks like everybody's complaining that Siri isn't a better Ask Jeeves, when that's not the design goal. What people expect is an LLM that has full access to the phone. Nobody's even remotely close to shipping that.

How is that even possible with modern transcribing and natural language capabilities?

I used to use it for that. A few months ago I got an Android system update and it no longer works for that. It just does web searches if I try. Now it's trying to push me into this thing where it takes a screenshot and tells me what's on the screen. I've never once cared about that.

Failing to find any way to get the alarm thing back, I turned off the entire assistant thing.

Same thing I used it for 10 years ago hahaha

I don’t think I’d want to talk to a voice assistant like that. Maybe it’s a generational thing? Things like that are ambiguous enough discussing them with human beings and a big part of things like voice assistants is understanding how it’s going to interpret and execute a response based on what I say to it.

I can believe that this is a case of the Software Engineering team being effective in a way that the AI/ML team wasn't. Apple's internal culture is notoriously closed and secretive, not the best way to approach cutting-edge AI research, especially when it wasn't their core competency in the first place.

But mainly I wanted to share that video because Craig Federighi calling the AI/ML team "AI/MLess" is one heck of a burn

I miss 411GOOG. It was fun and felt like a cool fusion of new and old tech.

the truth is ~none of us in the HN peanut gallery have any appreciation for what its like managing AI inside software inside Apple. it's less a technical role and more of an executive/politics/leadership role. im sure the disappointing progress shares a lot of blame and he was unfortunately the fall guy. estimated compensation $10-30m/yr for last 7 years tho...

Where did they fail besides Siri? The rest look like fine achievements to me.

>Seems like Khan is preparing the mothership

Nah, IS&T has always been under the CFO, and apparently some fraction of AIML is headed under them.

John Ternus is rumored to be the leading candidate for the next CEO. That would also make more sense in terms of age.

odd, why not Craig? he's by far the popular pick + probably actually right leader for apple's ai phase