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How Deep Are You Willing To Go?

Within ten minutes of my meeting a girlfriend’s mother, she was in tears, sharing a story with me that she’d never told another living soul.

That’s what people do when they speak to me. They open up…

My wife once said to me, “Why can’t you talk to my family about ‘normal’ stuff… like football?!”

I tried.

I really did.

I literally researched ‘how to make conversation about football’. Believe it or not, there are thousands of articles about this on Google.

But I couldn’t do it.

I didn’t actually care!

At a party you’ll almost always find me in the corner of the room, talking deeply to one person for the entire night…

Want to talk coaching, business, philosophy, politics, psychology, independent movies, life, death or human behavior? I’m your guy.

Want to talk about the game on the weekend, the weather or American Idol? I’ll stand there stammering or slack mouthed, without a clue what to say next!

This can be somewhat of a disadvantage in a social setting. (You know you’re an introvert when plans for a night out are cancelled and you’re secretly relieved!)

But I’ve turned it into my secret advantage when it comes to business.

I’ve been building a community of leaders for years, around the power of Deep Coaching and Deep Conversation.

I’m writing this piece at the end of a Deep Dive, where a small group of people traveled from as far away as New Zealand, to spend 3 days with me.

Non-stop for those 3 days, I’ve put them one at a time on a hot seat. And I’ve coached them – again and again and again.

I’ve asked them questions to challenge their thinking, such as:

  1. What’s the one question you have, that if it got answered, would change everything?
  2. If you could only work 2 hours a week – what would you focus on?
  3. What are you tolerating?
  4. What are you willing to struggle for?
  5. What’s your favorite flavor of failure? (We all know, in advance, how we usually fail at anything).

I took everyone out for dinner on the second night. But this wasn’t your usual dinner party.

I told them that I was going to ask an interesting question. And that we’d go around the table, taking turns to answer it.

I never know, in advance, what I’m going to ask. This time, I said, “What’s something surprising about you that most people would never know?”

Someone shared a story about working for President Obama. Someone had scared away a mountain lion – at a naked retreat center! And someone else had gone AWOL from the army when he was a teenager in the 60s. To punish him they put him in solitary confinement for over sixty days. He said it was the best thing that ever happened to him.

That’s my kind of conversation, when people respond, “What?! Tell me more…”

If you are tired of being the most interesting person in the room, come and join us…

If you like interesting conversations, with extraordinary people, come and join us…

If you’d like your own personal hot seat with me, there’s 1 spot left to join me in Europe, this July. And we’ve just opened the doors for 10 people to join me in Los Angeles, this December.

Bring along your biggest dreams and your deepest fears. Get ready to open up about what truly scares you. Be prepared to let me know what wakes you up at 3am, with tears running down the sides of your face.

Just don’t, whatever you do, talk to me about football!

Love. Rich


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