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At Taskrabbit all-company meetings, CEO Ania Smith has taken to instituting what she calls a “Nailed it, Failed it” segment. She asks her executive team—and encourages other employees—to publicly share their biggest flops, particularly when it relates to experimenting with AI.
“We do stand up very often and say, ‘I tried this, but it didn’t work,’ or ‘I tried that, but it didn’t work,’ to try to normalize a failure,” Smith said.
Smith was one of four C-suite executives I spoke with at the Fortune Most Powerful Women Summit in Washington, D.C. last week on a panel about women redefining work in the age of AI. Encouraging employees to experiment with AI—and giving them permission to fail along the way—was a big theme of our conversation.
When it comes to sharing the stories of things that haven’t gone according to plan, Emma Chalwin, Workday’s chief marketing officer, encouraged business leaders to “get more comfortable being uncomfortable.”
