Microsoft has been talking up Cortana a lot recently, but its own CEO failed to get it to work properly at one of the most public events to showcase it so far.

On Wednesday, Microsoft CEO Satya Nadella gave a keynote speech at Dreamforce, the big user conference held by Salesforce.


Nadella talked about artificial intelligence and walked up to the podium to showcase how Cortana, Microsoft's personal assistant software, is able to understand natural language queries.But then he asked Cortana, "Show me my most at-risk opportunities," and the software surfaced reminders to buy milk instead.

Nadella gave it a second try, but it failed to understand him again, causing a frustrated Nadella to say, "Oh man!" at one point.


As he failed a third time, Nadella seemed a bit frustrated, and apologized to the crowd, "Sorry about that. Someone's trying to save me from backstage."

Eventually, on his next try, he changed his query to "show me the most risky opportunities," and was able to get it to work.