Microsoft is well-known for its uncomfortable relationship with branding, but Cortana is the rare exception of them getting it just right. It almost didn’t happen.

“I chatted to Sandeep Paruchuri, my colleague from WhatsApp and a former PM at Microsoft, about Microsoft’s AI assistant, Cortana,” Alice Newton Rex writes in the most recent entry in the Big Bets newsletter. “A competitor to Siri and Google Now, Cortana was a bottom-up bet that became a major part of Microsoft’s strategy to make their Windows Phone succeed and to prove their prowess in the AI arena.”

Well, we all know how that turned out, but the most interesting part of this interview, perhaps, relates to branding.

“[Microsoft CEO Steve] Ballmer had poor product taste,” Mr. Paruchuri told Newton Rex. “He wanted the whole thing to be Microsoft branded. And then his parting gift [Ballmer would soon step down as CEO] was to try to name it Bingo. But we waited it out.”

Incoming CEO Satya Nadella had “different ideas” about the branding of Microsoft’s digital assistant, Newton Rex explains, and he “was a huge supporter of the project because of his belief in the power of AI. Under his leadership, Cortana got to keep her name and was declared ready to ship” as part of Windows Phone 8.1.

The newsletter also touches on the failures of Windows Phone and Cortana, and it’s a curiously insular take to believe that Cortana failed because of “too many cooks” syndrome. But that’s the story Paruchuri delivers.

“Everything that was right about the first release went wrong for the second release,” he said. Now, there were hundreds of Microsoft product managers “trying to get in on the action, and getting anything done required dozens of cross-company meetings,” Newton Rex writes. All of the new people diluted the original ethos they’d built and diluted the focus. They’d worked out how to scale their product but not their culture … With the rapid dilution, the brand faltered before it even had a chance to truly reach the masses.”

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