Great leaders must have the confidence to trust their gut and be the first to speak up when they see colleagues considering a bad idea — even if calling them out is uncomfortable, according to investor and author Eric Becker.

Failing to do either of those two things consistently can force your career to stall out, says Becker, the co-founder and co-chairman of Cresset Capital, a Chicago-based wealth management firm with more than $70 billion in assets under management. Becker, whose book “The Long Game: A Playbook of the World’s Most Enduring Companies” published on Oct. 14, has started or invested in more than 100 companies, he says.

In Becker’s experience, cooperation and teamwork are essential to any organization’s success, he says. However, your inclination to support your colleagues and be a team player can make it harder to voice dissent, even when you feel strongly that the group’s thinking could lead your organization down a hazardous path.

“What I’ve found is we have to listen to our guts more. But that’s not enough. We have to also exercise our uncomfortable conversation muscle,” says Becker.

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