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Microsoft's Version of Siri Fails to Work at the Worst Possible Moment (VIDEO) This was neither the time, nor the place, Cortana. Really, you should know better.

By Kim Lachance Shandrow

Opinions expressed by Entrepreneur contributors are their own.

ExpovistaTV | Youtube
Microsoft CEO Satya Nadella

Live demos are tricky. When they tank, it's supremely embarrassing. Just ask Satya Nadella. The Microsoft CEO tried to show off the tech giant's answer to Siri before a live audience at a recent Salesforce conference and he failed miserably. Or should we say Cortana failed him?

Here's a quick play-by-play of the humiliating clash between Nadella and the Microsoft's svelte-voiced virtual assistant, who apparently doesn't behave well -- or at all -- when it really counts, not even for the boss.

Related: Satya Nadella Proves Even Giants Can Pivot

Nadella: "Show me my most at-risk opportunities."
Cortana: "Show me to buy milk at this opportunity." Ah, maybe she's thirsty.
Nadella: "Uh, no. That's not what I want."
The crowd erupts in laughter. Even a conference emcee cracks up loudly into her microphone. Not good.
Nadella: "Let's try it again. Show me my most at-risk opportunities."
Nothing. Cortana is totally unresponsive.
Nadella: "Oh, come on!"
More giggles from the crowd. Awkward city.

Nadella, clearly agitated by this point, makes another go of it. He barks his original command again, this time with a "please" tacked on the end. Again, another fail. Blushing, Nadella sheepishly apologizes to the audience. He then realizes "someone" is trying to "save" him from backstage, moving the cursor for him, ironically a real, live personal assistant. Humans to the rescue again.

Unfortunately for Nadella and his employer, thanks to the unforgetting (and unforgiving) Internet, his mortifying public meltdown will live on in infamy forever. Check out the dashed show-and-tell below, starting at the 10:31 mark.

Perhaps the foiled demo is a touch of karma for Microsoft posting a live, on-stage Siri fail on MSN. You know what they say. What goes around comes around.

Related: 4 Ways the 'New' Microsoft Is Dramatically Different From the 'Old' Microsoft

Kim Lachance Shandrow

Senior Writer. Frequently covers cryptocurrency, future tech, social media, startups, gadgets and apps.

Kim Lachance Shandrow is a senior writer at Entrepreneur.com. 

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