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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Developing the confidence to trust your gut isn’t always easy, especially if you’re an employee starting a new career path or a first-time business founder. But having faith in your own intuition — particularly after doing extensive research, listening to alternative opinions and weighing multiple options — is crucial to becoming a confident, successful leader who identifies and seizes opportunities before they slip away.
“[It] starts with this sense that you have that something’s not right,” he says.
When that feeling pops up, it’s important you don’t ignore it, even if it means speaking up in a meeting or pulling aside a colleague to share your concerns, adds Becker.
“Somebody’s got to speak up,” he says. “And you should always be, at the end of the day, taking personal responsibility that you’ll be the one who speaks up if you’re going to be a leader.”
The importance of getting ‘comfortable with being uncomfortable’
Calling out a colleague for a bad idea or questioning your company’s direction can be awkward and difficult, which makes it “absolutely critical [to become] comfortable with being uncomfortable,” Becker says.
He’s not alone. Communication is a requisite skill for leaders, and the best communicators “have a tolerance for discomfort,” bestselling author and University of Houston research professor Brené Brown told The New York Times in October. Speaking up effectively when you want to call out a bad idea requires vulnerability and honesty, Brown said.
Uncomfortable conversations are both inevitable and necessary for personal success, and the success of any team or organization you want to lead, according to bestselling author and motivational speaker Simon Sinek. “The skill of having an uncomfortable conversation is essential,” Sinek said in a video posted to his YouTube channel in July 2023. “And the way you’re going to practice them is by actually having them.”
Kick off any difficult conversation with tact and transparency to avoid catching anyone off guard, Sinek recommended.
“I just had [a difficult conversation] recently with a friend and it went like this: ‘I need to have an uncomfortable conversation with you.’ By stating what’s about to happen, it lets the person take a deep breath and know what’s about to happen,” said Sinek. “It also lets them be prepared and be a little less defensive.”
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