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When Steve Jobs hired Tim Cook: How a 5-minute meeting convinced him to leave successful Compaq for struggling Apple

One CEO friend told Tim Cook he'd be a "fool" to leave Compaq. On paper, the move made no sense. Compaq was winning, Apple was on the verge of collapse.

September 17, 2025 / 20:19 IST
When Steve Jobs interviewed Tim Cook

When Steve Jobs interviewed Tim Cook

In 1998, Tim Cook had a great job. As an executive at Compaq, the world's biggest PC seller at the time, he was comfortable, successful and had no real reason to leave. So, when headhunters from Apple kept calling him, he politely said "no thanks." Again and again.

Apple, back then, was a very different company. It was struggling, almost broke and most people in the tech world thought it was a sinking ship. Just weeks earlier, Michael Dell, the founder of the hugely successful Dell Computers, had famously said that if he were in charge of Apple, he'd "shut it down and give the money back to the shareholders."

But the recruiters were persistent and finally all the efforts paid off. Cook wasn't interested in the job, but he was curious about the man behind the calls, Steve Jobs. "Steve created the whole industry that I'm in," Cook later recalled. He figured it would be worth it just to meet the legend.

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So, he agreed to a meeting, walking in with no intention of taking the job.

That meeting changed everything.

Sitting down one-on-one, Steve Jobs began to paint a picture of the future. While every other tech company was chasing corporate clients with servers and business software, Jobs was going the opposite way. He was betting everything on the consumer. He described a new kind of computer, one that was unlike anything anyone had ever seen.

In just five minutes, Cook's logical mind was overruled by his gut feeling. He looked at the massive problems Apple had and thought, "I can make a contribution here." Working with a visionary like Jobs, he decided, would be the "privilege of a lifetime."

Everyone he trusted told him to stay at Compaq. One CEO friend told him he'd be a "fool" to leave. On paper, the move made no sense. Compaq was winning and Apple was on the verge of collapse.

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But Cook realised that the experts were wrong. They didn't understand Steve's vision or his unique ability to see the world with fresh, "beginner's eyes." Cook decided to take the leap, trusting his instinct.

In March 1998, Steve Jobs officially hired the 37-year-old Tim Cook as Apple's head of worldwide operations. Cook inherited a mess, but with his expertise in supply chains and manufacturing, he became the perfect partner for Jobs. He was the operational genius who could turn Jobs's ideas into reality.

Jobs later said that Cook shared his vision and that he could trust him so completely that he could "just forget about a lot of things." It was a perfect match.

For Cook, the decision was about more than just a business strategy. Over the years, Jobs became more than a boss. He became a mentor and a dear friend. "He was one of the best mentors in the world," Cook said in an interview.

Saurav Pandey
Saurav Pandey is the Deputy Manager of Content at Moneycontrol, specialising in content strategy, execution and performance analysis. He integrates advanced SEO techniques to deliver high-impact, data-driven content formats. His expertise spans various beats, including education, career, science and others, where he adopts a technical approach to optimise visibility, improve search rankings, and drive organic traffic growth. He can be reached out at Saurav.Pandey@nw18.com.

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