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‘Oh, come on!’ Microsoft CEO pleads with Cortana to work properly during live demo

You have to feel for Satya Nadella. The Microsoft CEO found himself in a sticky situation this week when, during a keynote speech at an event in San Francisco, Cortana wouldn’t play ball.

Addressing a sizable audience at Salesforce’s annual Dreamforce conference, Nadella was happily demoing some Microsoft productivity tools when he decided to call on Cortana, which the computer giant describes as “your clever personal assistant,” to help him complete a task.

Related: Still skeptical about Cortana? These 10 features might change your mind

“Show me my most at-risk opportunities,” Nadella asked Microsoft’s Siri-like digital assistant.

After a slight pause, Cortana came back with the Google search query, “Show my to buy milk at this opportunity,” followed by some eight million results related to the nutrient-rich dairy product. But it wasn’t what he asked for.

With the milk-based results popping up on the screen, the audience laughed heartily before offering a round of applause.

Meanwhile, Nadella held it together and tried again.

Cortana, however, was having none of it, this time opening up Reminders to see if anything needed doing, which led the Microsoft CEO to emit a frustrated, “Oh, come on!”

Related: Is Cortana a dangerous step towards artificial intelligence?

“One last try,” said Nadella, who by this time was probably hoping for a trap door to open to take him away from the unfolding mess. Alas, it wasn’t third time lucky for the CEO, with Cortana failing to offer up anything useful regarding his most at-risk opportunities. “No, this is not going to work,” Nadella concluded.

With the presentation stalled, the Microsoft boss emitted a hopeful, “Is someone trying to save me from backstage?”, conjuring up the image of a team of sweating minions behind the curtain bashing away on laptops in an effort to save their boss from further humiliation. Thankfully, they did something right, allowing a relieved Nadella to return to the burning issue of risk and opportunity. Cortana wasn’t called upon again.

Awkward

While we all have moments where our smartphone’s voice assistant fails to correctly process what we’re saying, Nadella’s experience will have been more awkward than most. Still, at least Cortana users can presumably expect some sharp improvements after this week’s high-profile mishap.

Microsoft’s voice-activated assistant is available with Windows 10 and Windows Phone 8.1, with versions also planned for iOS, Android, and Xbox One.

If you want to check out Nadella’s Cortana misfire for yourself, it starts at the 10:30 mark in the video above.