Do you encourage troublemakers?

Whenever a company experiences a moment of major public backlash, Luvvie Ajayi Jones always asks the same question: “Who was in that meeting who did not say something?”

The founder and CEO of Chicago-based content strategy company Awe Luv Media, Ajayi Jones says that whether it’s a marketing campaign that missed that mark or a failed product launch, chances are that a few people around a conference table (or on a Zoom call) thought it was a bad idea but didn’t raise their concerns with the rest of the team. Why? According to Ajayi Jones, who has lectured on company culture at Google, Facebook, Microsoft, Twitter, and Nike, most corporate missteps can be traced to one thing: fear in the ranks. Employees are often afraid to have honest, difficult conversations with their colleagues or managers because their first instinct is to think: “What happens if somebody doesn’t like what I just said?”

To avoid this, Ajayi Jones recommends recruiting and cultivating a team of what she calls “professional troublemakers” who feel comfortable challenging others and disrupting company protocol. The best workplaces, she says, are those that root out prioritizing harmony over discomfort. This prevents the wasting of time and money on bad ideas that come to fruition only because no one felt empowered to object.

“We will lie our way through the world,” said Ajayi Jones, speaking Tuesday at the Tory Burch Foundation Embrace Ambition Summit in New York City. “It’s not that we’re bad people … It’s just that it’s easier sometimes to lie.”

Chiming in during a meeting with a question or criticism can be difficult, however, especially for newer or younger workers. Instill in the team that their opinions will not be met with punishment, Ajayi Jones says. And encourage employees to think about what’s at stake if they don’t speak up by asking themselves the question: “Will my silence convict me?”