What is CEO Coaching like? A live-recorded session with a CEO and bestselling author

I’ve been pouring my heart out on this blog for some time now, doing my best to share the lessons I’ve learned from coaching well over 100 CEOs, VCs, founders, entrepreneurs and otherwise successful and extraordinary people in my eyes.

Then it struck me: All of the writing and the insights and the sharing doesn’t quite capture it. It doesn’t quite go there to the actual experience of coaching. To me, it is a holy experience. Something where 2 people come together and leave as different humans. A part of them has died in that session and a new part has then emerged.

This, then makes it scary and exciting. You never know what you’re going to get, which new insights and which consequences you might want to consider after a truly deep and powerful session.

Something else came to me: No more explanations, no more writing, no more tips and tools and advice. I’ll just record sessions and put them live on this blog. Plain and simple. I acknowledge that it takes some extraordinary individuals who are willing to step into the ring with me and be vulnerable AND to share it with the rest of the world. But those that are willing to dare, I’m offering a wager to turn their lives upside down in a way that will be transformative.

The session: Carl Richards, CEO of Behavior Gap

Today, I’m excited to unveil one of those sessions, from a show that I’m calling “Out in the Open”. The person I’m coaching is no stranger to some:

• Today’s guest is Carl Richards
• He’s a bestselling author of the book The Behavior Gap
• He’s the CEO and founder of Behavior Gap
• He’s a columnist for the New York Times for over 10 years with his creation of The Sketch Guy column.
• Carl is also someone I deeply admire as a human who is willing to challenge his own status quo over and over again – the more successful someone becomes, the harder that gets in my experience.

Here is the show, it’s completely unedited, save for a brief catch up conversation that I’ve cut out at the end. Everything else, is pretty much exactly how a coaching session would unfold with a private client of mine:

My intention of putting live sessions out there has a few reasons:

• To show that successful entrepreneurs with million-dollar businesses still have fears, still work through their own difficulties and psychology like everyone else does
• To offer a kind of secondary coaching through these videos to anyone out there who isn’t able or ready to commit to their own coach, but gets value from seeing others go through similar problems.
• To show the power of coaching – for anyone who’s unsure whether this is valuable to make up their own mind from seeing Carl’s transformation and insights in this video.
• To encourage CEOs and leaders everywhere that receiving support and reaching out for support is a sign of true strength. And the paradigm of the leader that shoulders it all alone without any support is one that doesn’t serve us anymore.

Let me know in the comments below if you’re getting any value out of this and any questions you have from watching this.