Day 2 of How to Start a Coaching Conversation Like a Master Coach (The Mixtape):

By Toku

Five Questions I Stole from the World’s Best Coaches, Why They Work, and How to Use Them to Start Powerful Coaching Conversations Today!

This week I’m working on a series of post about my favorite opening questions / gambits / strategies of some of the world’s best and best-known coaches.

Yesterday we looked at a great OPEN/DROP question by Tony Robbins (“What’s changed?”) and today we’re going to look at the classic “What would make this an extraordinary conversation?” by Rich Litvin.

If you don’t know who Rich is, he co-wrote The Prosperous Coach, one of the most applauded books on coaching by many in the industry. I studied with Rich for over two years as a member of his high-level mastermind. In talking about this question, we’ll also be talking about the importance of using questions that align with your coaching style, and how the right question for someone else can be the wrong question for you.

Master Coaching Awesome OPENs Track / Question 2: What would make this an extraordinary conversation? (Rich Litvin)

Why it works: If you’ve watched Rich coach—even just a handful of times—you might think this is Rich’s favorite question. Look up almost any video of him coaching and you’ll likely encounter it. And I think the reason he uses it so often is twofold:

  1. It’s a great question.
  2. It works very well with Rich’s style and being.

Let’s start with #1: it’s a great question. The reason this is such a great question is that it asks the client to identify what it is that they really want. Rich, like most good coaches, understands that we mostly don’t ask for what we really want but what we think we can get. By asking people what would make this an extraordinary conversation he sets a context that:

  1. this is a different kind of conversation (not an ordinary one);
  2. this conversation and its result could be extraordinary or amazing;
  3. we have control over whether or not it is (we mostly think this is outside of our control); and
  4. finally, he gives the client permission to ask for what they want.

When you combine all of these together, Rich is getting a tremendous amount done in a single question.

Which brings us to point #2: it works well with Rich’s style and being. If you’ve ever watched Rich coach, you’ll notice he has an ability to create a natural sense of awe around him when he coaches.

Everything—from his British accent to his intense-but-kind gaze to his stylish dress—creates a sense of possibility and gentle intensity. It’s almost like a form of being hypnosis, not that different that what I’ve seen created by Tony Robbins or other great leaders and public figures.

What’s great about this question is it works in alignment with who Rich is. He embodies being extraordinary, he talks about it, spends time with people he describes as extraordinary, and has a way of telling others stories that makes you feel just how extraordinary they are. Because of this a question about a conversation being extraordinary works especially well.

Why I love it: I love it because it’s such a great example of a master using just the right weapon again and again and still finding it quite powerful. I think part of me would be driven insane asking the same question again and again, and yet the way Rich embodies the extraordinary when he asks it is powerful and fascinates me every time I see it, even when part of me wants to roll my eyes at the fact he’s asking it again. Even if I get bored of it, Rich never asks it in a boring way and this always deeply impresses me.

How you can use it: This is perhaps one of the easier questions on my mixtape for you to apply to your coaching right away. I have no hesitation offering this as a great opening question to a new or experienced coach. The question itself is so structurally good it kind of works no matter who you are or what conversation you’re in.

So if you want to take it out for a spin go right ahead. But as you practice with it, I’d love for you to pay attention to how the energy that exists in the conversation before you ask this question changes how well the question lands.

If you go straight from rapport to this question without any context setting, my experience is the question seems almost too heavy. Like trying to eat a jelly donut after a workout. But if you set a powerful context and use your presence to create awe, it seems to land much better. More like creme brulee after steak tartare. But try it out and see what you notice.

Also pay close attention to how people respond to this question, because it will give you an insight into how they respond to possibility in general. If they get confused or resistant, that’s likely how they respond to possibility. If they get excited and then a little scared, same thing. While this won’t reveal all of the possibility-avoidant tactics your clients will deploy, it will give you a little preview.

Finally, as you try this out notice how it goes with or conflicts with your natural style as a coach. Does it feel like you have to pretend to be someone you’re not when you deliver it? Or does it feel really in alignment with who you are. No matter what, try expanding your attention out to see what other questions feel like this. If you want to go question hunting (an odd but favorite pastime of many coaches), consider whether or not a question aligns with your style as a coach.


Okay—that’s all for today! If anybody has questions about using this or any other question as an opener to their coaching session please don’t hesitate to post a question below. I love having my ideas challenged! And for me, inquiry is the pathway to mastery.

And please come back tomorrow where we’ll be talking about Michael Neil’s Alt-Coach Question: “What if you didn’t have to have a question? What if we both looked in a direction and saw what there was to see?”


PS: Hey, did I mention all of this analysis was made possible by this simple coaching tool we created called the Coaching Canvas? You can get a free copy of it here:

PPS: Hey, did I also mention we’re doing a free Micro-Dojo webinar-class-teaching-thingy called

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