No matter the product, it’s always risky demoing software up on stage in front of a live audience. Software might work great during testing, but once you’re up on stage showcasing it to the world, Murphy’s Law has a strange way of sneaking up and rearing its ugly head. And if you’re so bold as to try and tempt fate by demoing voice recognition software in front of a large crowd, well, may the force be with you.

Unfortunately, and hilariously, this is a lesson that Microsoft CEO Satya Nadella had to learn the hard way this week. While presenting a keynote speech at Salesforce.com’s Dreamforce conference, Nadella decided to show the crowd what Cortana, Microsoft’s version of Siri, was capable of.

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What followed was every presenter’s worst nightmare.

Nadella, who had previously been talking about all things AI related, began by asking Cortana, “Show me my most at-risk opportunities. Cortana hilariously interpreted it as, “Show me to buy milk at this opportunity.”

Ouch.

Nadella tried once again. With the same command, Cortana misinterpreted it once more and began creating a reminder of some sort. Frustrated, Nadella aborted the action with a frustrated “aww, come on!”

Nadella then tried a third time before quickly realized that it wasn’t going to work, subsequently apologizing to the crowd. “Sorry about that,” he said.

While undoubtedly frustrating, Nadella seemed to handle it with as much poise and grace as one possibly could in such a scenario. Not to despair, Nadella finally got it to work after changing his command to “show me the most risky opportunities.”

Little did Nadella know, but using Cortana on stage was, itself, the riskiest endeavor of all.

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