Cortana: the not-so-intelligent PA embarrasses Microsoft CEO

The press event was meant to demonstrate the processing prowess of Microsoft’s digital personal assistant, but Cortana didn’t want to play ball

Embarrassing times: Microsoft's CEO, Satya Nadella, experiencing something of a defeat at Salesforce's annual Dreamforce conference after the company's digital personal assistant - Cortana - failed on him

The CEO of Microsoft, Satya Nadella, looked uncomfortable at Salesforce’s annual Dreamforce conference in San Francisco after his “clever personal assistant”, Cortana, chose to have a minor malfunction at the event.

Nadella was attempting to show off the productivity tools of Windows 10 and decided that he would ask the siri-esque assistant to help him do so.

The auditorium filled with laughter, much to the embarrassment of Microsoft’s CEO

“Show me my most at-risk opportunities,” Nadella asked Cortana.

But rather than coming back with a drop down list of meaningful information about Salesforce’s riskiest ventures, Cortana chose to search Google asking, “Show my to buy milk at this opportunity”.

The auditorium filled with laughter, much to the embarrassment of Microsoft’s CEO, but he calmly held his composure and tried again.

This time round the so-called intelligent personal assistant opened up the ‘Reminders’ application, causing Nadella to express his obvious frustration.

“Oh, come on!” cried Nadella, “one last try.”

But rather than it being a case of third times a charm, things just got worse, with Cortana deciding that it had had enough of being asking the same question over and over, offering up nothing at all.

It was at this point Nadella admitted defeated.

“No, this is not going to work,” he concluded.

After the slight mishap, the demonstration continued without a hitch, but Nadella didn’t call on his not-so-glamorous assistant for help for the remainder of the presentation.

For those looking to see the blunder for themselves, the action starts at the 10:30 mark in the video above.

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