Presenting on stage in front of an audience of hundreds or even thousands can be a daunting task. Add in some tech demos and the fact that millions may be watching live around the world and you’ve got a recipe ripe for failure – just ask Satya Nadella.

During a keynote at the Salesforce Dreamforce conference last night in which he was speaking with Jessi Hempel from Wired, Nadella attempted to show off some of what Cortana can do. As you’ll see in the clip above (skip to minute 10:15), Microsoft’s CEO asked the virtual assistant “show me my most at-risk opportunities.”

What Cortana heard was quite different: “Show me to buy milk at this opportunity.” Whoops.

Nadella kept his cool and tried again but it was clear that it wasn’t going to work. Fortunately, his team backstage was able to lend a helping hand.

Bonus video: Remember this one?

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