Watch Microsoft’s CEO Live Every Tech Leader’s Worst Nightmare

Uh, guys, I swear this worked last time I tried it…

This is what gives an entrepreneur night sweats: You’re up there on stage, camera rolling, showing off your awesome product in a live demo… and then the thing totally fails. And for Microsoft CEO Satya Nadella, that terrible scenario begins at 10:31 in this video:

Nadella was in front of Salesforce’s annual Dreamforce conference in San Francisco, and trying to show off Cortana, Microsoft’s version of Siri. He asked it a simple question: “Show me my most at-risk opportunities.”

Cortana’s translation: “Show me to buy milk at this opportunity.”

Nadella tried again. And failed again. And then, horrifyingly, failed again.

Then he gave up.

Think that’s bad? Try loading up Siri right now and asking it, “Show me my most at-risk opportunities.” You’ll get a bunch of news coverage about Cortana’s #fail, just as we did:

Doesn’t get much more embarrassing than that.