Investor and author Eric Becker says great leaders must trust their instincts and have the confidence to be the first to speak up when they see a colleague considering a bad idea, even if it makes them uncomfortable to criticize.
If you can’t do either of these two things consistently, Becker says, your career can stall. He is a co-founder and co-chairman of Cresset Capital. Cresset Capital is a Chicago-based wealth management firm with more than $70 billion in assets under management. Becker’s book, “The Long Game: Strategies for the World’s Most Enduring Companies,” was published on October 14th, and he has started or invested in more than 100 companies.
In Becker’s experience, cooperation and teamwork are essential to organizational success. However, because of your tendency to support your colleagues and want to be a team player, you may find it difficult to speak out against a group mentality even if you feel strongly that it could lead your organization down a dangerous path.
“What I realized is that we need to listen to our hearts more, but that’s not enough. We also have to exercise our uncomfortable conversation muscles,” Becker says.
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Developing the confidence to trust your intuition isn’t always easy, especially for employees or first-time entrepreneurs who are starting a new career path. But trusting your intuition, especially after doing extensive research, listening to alternative opinions, and weighing options, is critical to becoming a confident and successful leader who identifies and seizes opportunities before they slip away.
“It starts with a feeling that something is wrong,” he says.
When those feelings arise, Becker added, it’s important not to ignore them, even if it means speaking up in a meeting or stepping aside a colleague to share your concerns.
“Someone has to speak up,” he says. “And at the end of the day, if you’re going to be a leader, you always have to take personal responsibility to speak up.”
The importance of being “comfortable even when uncomfortable”
It can be uncomfortable and difficult to call out a co-worker for a bad idea or question the direction of a company, so it’s “absolutely important to get comfortable with being uncomfortable,” Becker says.
he is not alone. Communication is an essential skill for leaders, and the best communicators “can tolerate discomfort,” best-selling author and University of Houston research professor Brené Brown told the New York Times in October. Brown said it takes vulnerability and honesty to effectively speak up when you want to point out a bad idea.
According to best-selling author and motivational speaker Simon Sinek, uncomfortable conversations are inevitable and necessary for not only your personal success, but the success of the team or organization you want to lead. “The skill of having uncomfortable conversations is essential,” Sinek said in a video posted to his YouTube channel in July 2023. “And the way to practice having that conversation is to actually have it.”
Sinek recommended starting difficult conversations with tact and transparency so no one is caught off guard.
“I recently had a[difficult conversation]with a friend, and it went like this: ‘I need to have an uncomfortable conversation.’ Stating what’s going to happen allows the other person to take a deep breath and figure out what’s going to happen,” Sinek said. “It also helps you get ready and your defenses can drop a little bit.”
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