As Apple navigates one of the most critical leadership transitions in its history, questions loom over its future direction in a rapidly evolving tech landscape. With several top executives nearing retirement—including Chief Operating Officer Jeff Williams and CFO Luca Maestri—the company is confronting a generational shift just as it faces mounting pressure to catch up in artificial intelligence and innovation. CEO Tim Cook, who has led Apple for 14 years, remains at the helm for now, but the conversation around succession is growing louder. It’s a moment that echoes a familiar anxiety from the company’s past—one Tripp Mickle captured vividly.

In his pathbreaking book After Steve: How Apple Became a Trillion-Dollar Company and Lost Its Soul, Mickle noted that before his death, Steve Jobs made a concerted effort to preserve Apple's unity and long-term vision, urging key executives to stay on and support CEO Tim Cook’s leadership.

“Jobs wanted Apple to defy the fate of Disney, Polaroid, and Sony. Before his death, Jobs pressed to keep the legs of Apple's starfish together. ‘Tim (is) going to need you,’ he told them,” writes Mickle in his 2022 book.

As Mickle described the Cook era as a triumph of method over magic, and with Cook turning 65 this November, a question lingers for Apple again, a decade and a half after Jobs: Who after Cook?

Will Apple follow the fate of BlackBerry and Nokia, or Microsoft and Cisco?

As Apple enters a critical transition phase, the question of its future — and who will lead it — has never been more relevant. Steve Jobs, in the final months of his life, was adamant about keeping Apple’s leadership stable.

As Mickle writes, “to keep the legs of Apple's starfish together,” Jobs pushed members “to commit to remaining several more years at the company.”

But that once tightly held leadership structure is now beginning to shift, as Apple experiences its most significant management shake-up in decades.

Chief Operating Officer (COO) Jeff Williams, Cook’s longtime second-in-command, will retire by the end of the year. Sabih Khan will take over operations from Williams, but he is only marginally younger and not viewed as a long-term successor, as Bloomberg’s Mark Gurman writes in his recent Power On newsletter.

Chief Financial Officer (CFO) Luca Maestri has already begun transitioning his role to Kevan Parekh. Several other senior executives, including marketing head Greg Joswiak, App Store chief Phil Schiller, environment lead Lisa Jackson, and chip head Johny Srouji, are in their 60s and nearing retirement.

Even AI head John Giannandrea’s future remains uncertain. As per Gurman, nearly half of CEO Tim Cook’s roughly 20 direct reports are nearing retirement.

As a result, this wave of exits comes at a time when Apple is under pressure like never before. Its AI strategy is faltering, lagging behind rivals like Google, Meta, and OpenAI. And as the company pivots more toward services and recurring revenue, questions are mounting about whether it can still lead in innovation — the very foundation of its brand.

“Apple users are not in a rush to ask for (AI features), because they are locked into the ecosystem. So, if you are an iPhone user, you are not going to switch to an Android just because of AI. There is a flywheel effect which is still strong for Apple, because AI (might be) important, it is not a make-or-break situation for Apple users at this point. Apple knows that (it) still has time. But what has worked for them for last 15 years will not work for next 15,” Neil Shah, co-founder and VP – Research, Counterpoint Research, tells Fortune India.

What makes the succession conversation even more significant is the broader context. Cook’s one-time partner in product design and Jobs’s creative soulmate, Jony Ive, is now collaborating with OpenAI’s Sam Altman on an AI-powered audio wearable device.

Still, history offers two possible paths. BlackBerry and Nokia, once giants, failed to evolve quickly enough and were overtaken. But companies like Microsoft and Cisco show that legacy tech firms can reinvent themselves under the right leadership.

Satya Nadella has been with Microsoft since 1992 and became CEO in 2014 after holding key leadership roles, including leading its cloud division. Similarly, Chuck Robbins joined Cisco in 1997 and became CEO in 2015, marking around 27 years with the company.

Yet, Cook has served as Apple's CEO for 14 years — a longer tenure than both Satya Nadella at Microsoft (11 years) and Chuck Robbins at Cisco (10 years).

Apple’s challenge now is to ensure it doesn’t drift into stagnation as its top leadership ages out. The Cook era has delivered consistency and massive financial growth.

But as Apple stares down its biggest leadership transition since Jobs’ passing, the real question is: can it still lead the next wave of technological reinvention, or will it simply optimise what it has already built?

Who is expected to take over after Cook?

Gurman, in his newsletter, reported that while the announcement of Williams’ retirement adds to the succession mystery, Cook is not expected to go anywhere anytime soon.

Cook is expected to remain at the helm for at least another five years, much like other long-serving corporate leaders such as Disney’s Bob Iger and JPMorgan’s Jamie Dimon.

Gurman writes that Apple’s board also largely comprises Cook loyalists, who are unlikely to push for change. Despite the CEO facing criticism for the company’s stagnating product innovation and frayed developer relations, his track record of leading the company through the post-Steve Jobs era and significantly boosting its market value still commands board confidence.

As chairman Arthur Levinson nears retirement, Gurman notes it is possible that Cook could assume that role as well, further consolidating his control over Apple.

Meanwhile, as Williams retires, Apple is redistributing his responsibilities across the company. The design team will now report directly to CEO Tim Cook, with likely consolidation under Alan Dye (VP of human interface) and Molly Anderson (VP of industrial design).

Although Apple previously claimed that Williams oversaw the Apple Watch and health hardware, according to Gurman, those responsibilities had already shifted to hardware engineering chief John Ternus about three years ago.

The software side of Apple’s health efforts — including the watchOS team led by David Clark and the health software group under Evan Doll — will move to Craig Federighi’s software engineering division. Dr. Sumbul Desai’s health products group is also expected to come under Federighi’s oversight.

Meanwhile, the Fitness+ subscription service, led by Jay Blahnik, is expected to be absorbed into Apple’s broader services group, which already manages offerings like TV+, Music, and iCloud.

The AppleCare division, headed by Farrel Farhoudi, is expected to move into Sabih Khan’s newly expanded COO organisation.

Finally, the Greater China team, under Isabel Ge Mahe, will retain its dual-reporting structure to both Cook and Khan, continuing the arrangement that previously included Williams.

However, Gurman notes that for the long term, John Ternus, Senior VP of Hardware Engineering, is the most likely candidate to eventually succeed Tim Cook. Ternus is younger and has been with Apple for over two decades. He fits the mould of a product-focused leader, though he lacks financial and operational depth and would need strong deputies.

In the event of an emergency, Apple would likely be led by a committee of top executives, including Khan, finance chief Luca Maestri, and veteran Deirdre O’Brien.

Meanwhile, Shah anticipates that the change in the strategy for the company will come from the design team. As a result, he says that while Ternus might be the next in line for leadership, there will be a need for equally important design and software leadership to support him.

Talking about the changes, Counterpoint’s Shah points out that while the design team will remain central to the process, much of the focus is expected to shift towards teams that manage infrastructure and data systems—particularly those involved in collecting user data and training AI models.

“Design team would be at forefront of it, but at the same time it would be more of the team which (has the) infrastructure and a system to collect the user data and train the models right. The software team will [hence] be fundamental (for) this. Hardware obviously has been important for Apple in terms of differentiation, but the game has moved away from hardware, given everyone can innovate with hardware because the supply chain is common now. (Thus,) the beauty lies in software and how you integrate AI and how you make it personalised and private. I think that is where [the next Apple] leader [will come from] who understands that particular thing. It could be from software, from design,” Shah says.

However, for now Shah agrees that the change in the vision for the company will only be brought by its forerunners – Tim Cook and Craig Federighi.