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Behind the scenes, Siri's failed iOS 18 upgrade was a decade-long managerial car crash

An example of a contextual query Siri will be able to answer, eventually. - Image Credit: Apple

The long-delayed overhaul of Siri was hit by repeated failures to progress, with leadership problems making it harder to execute than it should've been.

In March, Apple admitted that its attempt to make Siri more personalized and up to date was far behind schedule. It confirmed that there were delays in getting Siri to the state where the company wanted it to be, and that it would be sorted out in the coming year.

Since that rare admittance from Apple, the company has done what it can to fix the situation. This included a managerial reshuffle, pushing John Giannandrea out of the top Siri role in favor of Mike Rockwell.

It was a major event in a situation that was extremely embarrassing to Apple. However, the entire affair is something that could have been avoided, reports The Information, had Siri not fallen victim to poor leadership choices.

Siri hot potato

Multiple people who worked in the AI and software engineering groups within Apple told the report that conflicting personalities were a problem. Some, who worked under the AI and machine learning group under Giannandrea said that poor leadership was at play.

The sources also identified Robby Walker, who worked under Giannandrea, as being one of the reasons for the issues, due to an apparent lack of ambition and willingness to take risks on future Siri designs.

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The employees also referred to Siri as a "hot potato" within Apple, due to it being passed between the different teams over the years. With the latest reshuffle putting Siri under the oversight of software boss Craig Federighi, they have some hope that favorable changes will be made.

A lengthy Siri issue

The problems getting Siri modernized started years ago, in 2018, when Giannandrea moved from Google to work on Apple's new AI group. At a time when Siri was beginning to stagnate, Giannandrea took an interest in managing the digital assistant.

Before then, engineers working on Siri felt as if they were second-class citizens with Apple, with frustrations that the software engineering team's control over iOS updates failing to prioritize Siri fixes. Those software engineers also felt the Siri team weren't able to keep up with new features being developed in the group.

Giannandrea's plan was to make Apple's own AI-based voice assistant, using a playbook he gleaned from Google. He believed Apple had to get better training data, and to do better at web-scraping for answers.

However, when urged to shake up Siri's leadership, he declined to do so.

Walker's safe work

The lack of risk-taking by Walker was a problem, the group of sources added. It was believed that Walker downplayed efforts to swing for the fences, and instead worked on other less meaningful metrics.

This apparently included celebrations of small wins, like reducing the response time for user queries. His work to remove "Hey" from "Hey Siri" also took more than two years to pull off, with little actual real benefit in the end.

Walker also dismissed one attempt in 2023 for one team to use LLMs for Siri to gain emotional sensitivity, such as to detect if a user is in distress. He said he would rather focus on the next Siri release instead of committing resources to the effort.

That team still went away to work on the project via the software engineering group's safety and location team, without his knowledge.

Increased tension

The software engineering group and the AI team had a dysfunctional relationship, with respective leaders Federighi and Giannandrea having dramatically different managing styles.

Resentments also built up over difference in pay, the speed of promotions in the AI group, and vacation periods.

Eventually, Federighi's groups started to mass together hundreds of machine learning engineers to work on its own models, separate from the main AI team. This included building demos to voice-control apps without Siri, which the Siri team didn't appreciate.

An attempt to introduce voice control systems for apps on a headset that would become the Apple Vision Pro was also problem-filled. Hostility between Walker and others in the group, as well as the slowness of the Siri group in general, became a big point of friction once again.

When ChatGPT was released in 2022, the AI group didn't respond with any real urgency, the engineers claim. By contrast the software engineering group were far more interested, with demos presented to Federighi of what could be accomplished.

Eventually, Apple's managers said in 2023 that engineers couldn't include external models in Apple products. But, the responsibility to build the models was the responsibility of the AI group.

They also apparently didn't perform as well as OpenAI's offerings, employees explained.

The current shakeup

Despite years of issues, the current situation where the Federighi-controlled software engineering groups would oversee the AI work led by Rockwell should be a fruitful one for Siri's progress.

Federighi is viewed as having more knowledge of technical details than many under his control. He has also told Siri's machine learning engineers to do whatever they need to make the best AI features, even if it's using open-source models from other companies.

Meanwhile Rockwell, who has a good track record in the company, is viewed as someone with vision, which Walker certainly lacked.

19 Comments

gatorguy 14 Years · 24702 comments

Regarding Apple’s Siri demo at WWDC last year, where the "new Siri" is asked about her mom’s flight landing and lunch plans:

"Among members of the Siri team at Apple, though, the demonstration was a surprise. They had never seen working versions of the capabilities, according to a former Apple employee. At the time, the only new feature from the demonstration that was activated for test devices was a pulsing, colorful ribbon that appeared on the edges of the iPhone’s screen when a user invoked Siri, the former employee said.

In other words the demo was faked and Siri had no such capabilities. It's good to see Federighi jump in and taking point, particularly with relaxing privacy focus just a tiny bit and allowing 

open-source third-party models.
 New leadership from the executive team, kudos. Perhaps something will actually be developed now. 

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Vision1 5 Years · 10 comments

Giannandrea came from Google, but he was never trained to think the Apple way. One of the reasons Apple worked so well for so long is because it thought different — a mindset Steve Jobs instilled deeply in the company. That way of thinking shouldn’t be assumed; it must be taught. If Apple wants to keep its soul intact, it needs to train new people in the culture that made it great. Hope they will learn from it. 

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tht 24 Years · 5821 comments

Well, it's the usual. It takes failures at a few levels for situations like this to arise.

Cook never should have structured the org such that AI and software are separate organizations. AI, ML and LLM algorithms seem pretty intricately tied to software. If there needed to be a Siri service owner, it should have been Product Marketing (Joswiak)? Then, Giannandrea was not good at his job. This is me looking from the outside. Maybe he was a good leader, but his org hasn't been very productive. I don't know who's responsible, but my experience with the software keyboard has not been good. It's been passable? At times, its key tapping performance and word prediction performance has regressed. That's an ML task that was under Federighi or Giannandrea? Either way, it's now an ML based keyboard that doesn't seem any better than the past.

Then, the overarching umbrella here is LLMs and chatbots. Everyone is desperate to create AI features. Most of them are of dubious benefit, but everyone has to be in the race. That's basically not Apple's MO, where they try to create beneficial features at their own pace. The company is in conflict with itself with AI. Not a good place to be.

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mpantone 19 Years · 2369 comments

It's hard to teach an old dog new tricks and Giannandrea is no spring chicken or recent college graduate. If there was a corporate culture mismatch then it is Apple's fault for putting him in his previous role. Apple has made mistakes before picking senior executives (Mark Papermaster, John Browett are two off the top of my head) who didn't fit the Apple Way.

Giannandrea had a good track record at Google so clearly he's smart. But being a great researcher is not the same as being a manager who will be rightfully judged by making product deadlines.

This isn't entirely Giannandrea's fault. Ultimately Apple failed in putting someone responsible for maintaining and improving Siri after their acquisition and now that hopping about the AI bandwagon is a top priority, a decade's worth of neglect has come back to bite them hard. Apple created their current conundrum by mismanaging Siri for years before they handed Giannandrea the torch.

They cannot fix Siri in a year and it's clear as day now. 

My guess is they tried and belatedly came to the conclusion that they have to rewrite Siri from scratch to interface correctly with current and emerging AI technologies. This is far harder for Apple than most other companies because Apple has placed security and privacy as two pillars of their core values.

The peanut gallery who has been whining for years that Siri was falling behind the competition was right all along.

Someday Apple will put out a useful Siri but it will trail the competition for several more years. It's notable that Apple Maps has never caught up to Google Maps especially when you look at the two side-by-side in many places outside of the USA.

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tht 24 Years · 5821 comments

mpantone said:
It's hard to teach an old dog new tricks and
This isn't entirely Giannandrea's fault. Ultimately Apple failed in putting someone responsible for maintaining and improving Siri after their acquisition and now that hopping about the AI bandwagon is a top priority, a decade's worth of neglect has come back to bite them hard. Apple created their current conundrum by mismanaging Siri for years before they handed Giannandrea the torch.

Someday Apple will put out a useful Siri but it will trail the competition for several more years. It's notable that Apple Maps has never caught up to Google Maps especially when you look at the two side-by-side in many places outside of the USA.

My pet hypothesis is that Siri was Scott Forstall’s baby. He pushed for the acquisition of SRI or Siri and lead the integration of it into iOS. After Forstall was fired, nobody wanted it and Apple only did the minimum to keep it going as a feature in their products. There wasn’t anyone in leadership to push it forward. 


Giannandrea was not passionate about it either after getting ownership of the service. Either that, or he simply wasn’t able to get improvements into production. Obviously bad either way. 

There are good reasons to be skeptical of voice interfaces. It’s not like in TV or movies, like the Star Trek ship computer or Tony Stark’s Jarvis. These pop-culture AI voice interfaces are basically magic, where you say something, in like 10 words, and the computer will design and build an tachyon field generator for you. 

Voice interfaces are high cognitive load, vague low density interfaces. They will generally suck for anything of mild complexity or more. People will revert to written language and pointing device (WIMP) interfaces to do most everything as it is easier, less taxing and faster. This is one of the reasons that all the voice digital assistants failed or didn’t take off. 

Apple knows this. They take a rather slow approach on voice interfaces? Other companies? They have all failed, right? The Sam Altman, Jony Ive voice gadget interface will also fail. 

The success (?) of LLM chatbots is all based on WIMP. You need to have a keyboard and display for to be useful. Even here, I sometimes think that this or that person spent an hour written a productive prompt input to get a chatbot to write a piece of code or text when they could have done the same or better job doing it themselves for an hour. 

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