Microsoft CEO Satya Nadella is flustered by virtual personal assistant Cortana's inability to understand his voice command. ExpoVistaTV/YouTube video screenshot

SAN FRANCISCO, Sept. 17 (UPI) -- Microsoft boss Satya Nadella had an embarrassing moment at a California conference when he attempted to show off virtual assistant Cortana.

The chief executive officer was addressing Salesforce's annual Dreamforce conference in San Francisco when he attempted to show off Cortana's ability to understand voice commands and deliver relevant results by saying, "Show me my most at-risk opportunities."


Cortana "Show me to buy milk at this opportunity."

Nadella made a second attempt with the same command, leading Cortana to open up his reminders.

The Microsoft boss, who was using a Windows 10 machine to run the personal digital assistant app, gave up after a failed third attempt.

Nadella's Cortana troubles begin around the video's 10:31 mark.