Meet the Startup Founder Coaching CEOs on Mindfulness

by

Can ‘radical self inquiry’ make you a better leader?

Man standing atop a mountain with arms spread wide

Work does not have to destroy us. Work can be the way we achieve our fullest self.

This is one of the mantras of Jerry Colonna, an executive coach, public speaker and ‘C-Suite Groomer’ who has helped some of the most powerful founders and CEOs to lean into leadership – by battling their demons. The former CEO of Etsy, Chad Dickerson, says there’s a “secret society” of people who’ve been coached by him, SoundCloud’s Alexander Ljung sees him and the founder of Gimlet Media, Alex Blumberg, broadcast a podcast of their revealing session, where his business blockages were linked to his relationship with his father.

“We take clients on a path to radical self-inquiry,” says Jerry, “This is different to self-enquiry. Inquiry refers to a process of investigation​. We define it as the process by which self-deception becomes so skilfully and compassionately exposed that there’s no mask that can hide us anymore.” Ready to dig deep? We quizzed the founder of Reboot about how he makes the C-suite cry – and then thrive.

Look back to move forward

Is your leadership style impacted by your own issues? Is an influence from your past affecting how you engineer your future? “We are all motivated by sometimes unconscious needs and wishes. Until we allow ourselves to become aware of those motivations, they’ll direct our lives,” says Jerry. “There are common issues I hear from people at an executive level – fear of failure, a sense of complete overwhelm, the impostor syndrome.” The inquiry process helps people to identify where these feelings come from. “So, the CEO who, as a girl, grew up scared and hungry may build a team motivated primarily by greed,” he says, “Or take the client who, late in their life, can’t decide what to do about a career move. He finally recognises that most of their previous career ‘decisions’ were not, in fact, decisions as much as attempts to finally prove their father wrong. They can then move past that old structure and make more conscious choices.”

“There are common issues I hear from people at an executive level – fear of failure, a sense of complete overwhelm, the impostor syndrome.”

Stand still with your hair on fire

As a follower of Buddhism, part of Jerry’s teaching focuses on mindfulness. “Radical self-inquiry is really another word for true mindfulness,” he says, “Mindfulness is not ‘blissing out’ and ‘stress reduction’ – although it can reduce stress. It’s, in fact, waking up. Waking up to all that is at play in your mind, waking up to all that is going on for your colleagues.” In a blog post, he described running a startup as feeling as if you’re “standing still while your hair is on fire.” When you feel panicked, pause! “For me it evokes the image of the teacher, walking into a room filled with screaming five-year-olds,” he says. “Should you scream louder? Of course not; the right thing to do is to shut the lights and, if they’re especially rambunctious, make them put their heads down on the desk for a nap. It works for five-year-olds. It works for your employees. And it works for the crazy thoughts in your head.”

Fix yourself first

As leaders, it can be tempting to focus on staff improvement, which is beneficial, but don’t forget to turn your eyes inwards. Jerry believes that, to create company cultures that nurture the emotional health of employees, founders need to “model it” themselves. “Be unafraid to encounter your own weaknesses and your own imperfections,” he says. “Be willing to look in the mirror and discover your blind spots. You’ll find that’s the source of your superpowers.” During the weekly ‘Wednesday morning group’ he attends (“yes, it’s a therapy group”) they follow the ‘No fixing rule’ proposed by the Centre for Courage and Renewal – you can encourage each other, but commit to not fixing, advising, “saving” or correcting another person who is on their own journey.

“Be unafraid to encounter your own weaknesses and your own imperfections. Be willing to look in the mirror and discover your blind spots. You’ll find that’s the source of your superpowers.”

Find solidarity in the startup scene

As part of his work, Jerry helps executives overcome the inevitable loneliness of life at the top by encouraging them to “mindfully attend to the unconscious sharing that undergrids every relationship. Part of this is acknowledging that it’s okay to admit you’ve sought help in the first place.Being open about the ways in which we strive to grow reduces the collective shame,” he says, “It’s shame more than anything else that stops people from seeking help.” Connect with a peer, a colleague or a mentor on a deeper level. “A few weeks ago, I watched a client speak at a company all-hands and weep with joy and broken-hearted love for his family and for the gift that are his colleagues,” he says, “I saw dozens of eyes soften and know that this place is a place where it’s safe for humans to be human.”

We would love to hear your thoughts:

Your email address will not be published. Required fields are marked *