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Bill Gates Reveals his “Greatest Mistake Ever” as Microsoft Boss

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Bill Gates has been reflecting on crucial decisions he made over Microsoft’s mobile operating system during his time at the company. In a recent interview with venture capital firm Village Global, the Microsoft co-founder disclosed that Microsoft’s failure to grab Android opportunity was his “greatest mistake ever”.

Bill Gates

The software world, particularly platforms are “winner-take-all markets,” and the mobile operating system is a natural thing for Microsoft to win. “The greatest mistake ever is whatever mismanagement I engaged in that caused Microsoft not to be what Android is,” Bill Gates said.

Former Google CEO Eric Schmidt acknowledged that the company’s ultimate goal was to beat Microsoft’s early Windows Mobile efforts when Google acquired Android in 2005 for $50 million. “We were very concerned that Microsoft’s mobile strategy would be successful,” Schmidt said in 2012. Android saw to the death of Windows Phone and Windows Mobile and became the dominant mobile operating system.

However, most people are surprised that Gates is taking the blame. Microsoft’s failure to win the mobile operating system market is supposedly in Steve Ballmer’s era. Ballmer couldn’t realize the opportunity “touch-friendly” era was bringing when he famously laughed at iPhone for not having a keyboard, saying it’s the “most expensive phone in the world and it doesn’t appeal to business customers because it doesn’t have a keyboard.”

Ballmer’s era played a major role in Microsoft’s mistakes in the mobile market. The company spent months arguing internally if it should scrap Microsoft Windows Mobile efforts, which had no touch-friendly feature at that time. Microsoft had an emergency meeting in December 2008 during which it decided to completely reboot its mobile efforts with Windows Phone and to scrap Windows Mobile.

It’s very likely that the company acted based on Bill Gates’ advice, though Microsoft’s Experience and Device division vice president Joe Belfiore and former Windows chief Terry Myerson were involved in that meeting. Gates assumed the role of chief software architect at Microsoft after stepping down as the CEO in 2000 during Windows Vista mishap. He eventually dropped the role in July 2008 and continued as chairman until 2014 when Satya Nadella became CEO.

In 2018, Microsoft’s Edge team sought Gates thoughts about moving the company to Chromium. According to TheVerge, Bill Gates, who now uses an Android phone, has in recent years been assisting on a mysterious “personal agent” project at Microsoft.

Though Gates was not directly involved in management decisions surrounding Windows Mobile, his departure from Microsoft came in the middle of the company’s failure to win the mobile market. Former Microsoft CEO Steve Ballmer, who was active during the evolution of touch-friendly feature, said his greatest regret at the company was Windows Vista before his tragic farewell.

Microsoft is grateful to be leading and waxing strong in some areas despite various challenges, including the famous antitrust lawsuit. “It’s amazing to me that having made one of the greatest mistakes of all time,… our other assets like Windows and Office are still very strong, so we are a leading company,” Gates says. Microsoft would have been a much stronger company if it had won the Android opportunity.

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