Cortana could be the best virtual assistant in the market, but that does not mean that she would obey her boss’s commands all the time. When the Microsoft CEO tried to show off Windows 10’s most hyped feature, it left him embarrassed, since the virtual assistant was not able to recognize his voice commands.

Cortana trolled Satya Nadella when he was demonstrating its features at a Salesforce Conference, two days back. He was delivering a keynote address and in the middle of his presentation, the CEO attempted to use voice commands to demonstrate some productivity features. But that actually turned out to be a waste of time.

“Show me my most at-risk opportunities,” he said. Cortana trolled Satya Nadella by opening up a Bing search result page for the query “Show me to buy milk at this opportunity”. Whoops!

Everyone sitting in the conference room broke out in laughter. Nadella laughed with them, trying to hide his embarrassment and asked Cortana the same question again. Now, Cortana tried to open up the reminders page.

A rather frustrated Nadella said ‘Oh, Come on!” and tried again. This time, it failed him again and Nadella gave up. “This is not going to work, sorry about that, he said”.

However, the video clearly shows that Nadella’s pronunciation of ‘at-risk’ could easily be misinterpreted even by a common human being. In his first attempt, he fumbled with the voice query. Cortana could have cracked it if Nadella had spoken a bit slower.