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Coaching on the Drop


Toku riffs on and answers questions about the Drop phase of the coaching conversation, focused on the idea of the Drop becoming a “clearing for possibility”: creating a space for possibility to be present for the client.

And throws in a few Dad jokes…


Get your own copy of the Coaching Canvas here.

Mastering “The Drop” as a Coach Is Like Mastering Great Sex as a Human


We named the Drop “the Drop” because it’s hard to discern. It’s a little like great meditation or great sex. When it happens, it’s obvious.

That was HOT!

WOW! My mind was BLANK!

But in the moment it’s happening, it’s sort of just happening.

We named it the Drop because it reminded us of surfing, or snowboarding, or skiing. There’s just this moment where you Drop in. It feels perfect and free. You can create the conditions for it, but when it happens it feels like it happens all on it’s own.

So How Do You Practice That?

Well, you practice it the same way you might practice surfing. You get in position, you watch the waves, and at the right moment you paddle. And you hope to catch the wave. Sometimes you do, sometimes you don’t. But that’s okay. After all, we’re surfing, right?

Well, here’s how you can do it.

Figure Out What the Client Wants

I know this seems too simple. But this is actually very hard to do. Most coaches never figure out what a client really wants. They only learn about the strategy the client has created to get it.

You start a coaching session and you ask the client, “What would you like?”

And they say, “I’d like to make a lot of money.”

“GREAT!” you say, “Let’s come up with some ways for you to do that.”

This is how most mediocre coaching sessions go. The client and the coach talk about money, they come up with ways to make it, the client takes some action and either does or doesn’t make some money. If the client is lucky, they won’t make any money.

That might confuse you. But in truth, making money won’t give the client what they want. At least not most of the time. Because the client doesn’t want money. They want what money will give them.


If you’re better than most coaches, you’re rolling your eyes right now. Of course you know this. But before you get too smart: SLOW DOWN, CHAMP. You probably are also not Dropping—or at least not as deeply as you could.

If you’re a good coach, you’ll say, “Hmm, money. Great. Well, why do you want money?”

And client will say, “Well, I used to have a lot of money, but then I lost it all. I need to get back to having money so I can move out of my parents’ house.”

“Great, so what you really want is to move out of your parents’ house. Great. Let’s talk about how you feel about living with your parents.”

This is pretty good coaching, I mean it’s not really about the money, right? There’s more to this story. But this still might not be the Drop. This isn’t totally what the client wants.

What Coaching Really Is

Now I’m going to make a statement about what I think coaching really is. Some people might disagree with me, so I’ll just say this is my assertion, not the truth of coaching.

For me, coaching is about helping our clients create themselves as condition-less beings.

Basically clients always have it that there’s some place else to get to. And in that place, they can have what they want, and when they have that they can be who they want to be.

This isn’t true. You can be whoever you want to be right now. You just don’t realize it.

Of course this doesn’t mean there isn’t work to be done. There is. But doing has to come from a foundation of being, and being is by its very nature condition-less—or at least it can be.

This is why, if you want to be a great coach, your Drops need to move toward the condition-less. Not absolutely; you can have a great session about the conditions, but first you need to get a context of being. “Moving out of my parents’ house” is a condition. “Making money” is a condition.

For me, to truly Drop you need a context of who the person will become.

In the example we’ve been working, I might ask: “So what would moving out of your parents’ house do for you?”

“You know, I’m not sure. It just feels like I can’t be myself around them. Sometimes it doesn’t feel like I can ever be myself.”

Okay, so I cheated a little bit. Clients don’t always get there that fast, but I’m writing this narrative so I made the client easy for myself. Do you see the Drop now? Do you see the context?

The Drop is in helping the client be themselves: “I can be myself no matter where I am, no matter how much money I have, no matter where I’m living.”

THIS IS SOMETHING TO COACH AROUND. Money, living with my parents, getting a job—those are things. And you can coach around anything, but they aren’t something, not really. But being yourself, coming from yourself, that’s SOMETHING!

Okay, now for your turn: the next time you coach, figure out: what do they really want? What is the condition-less state they are trying to get to? Do this as you coach AND do it afterwards. Reflect: where is this client trying to get to? What is the condition less state they are seeking?

And see how it shifts your coaching.

A Note about Condition-less-ness

So conditions are always arising. This is normal. The odd thing about coaching a client to a condition-less state is that being there is a practice. It’s like meditation. The point of meditation is to just be. Or at least the point of Zen meditation. Just being is hard to achieve, and also you’re always achieving it.

It requires practice to just be, but you are always just being on some level. Don’t get too mixed up by this. Just remember. Your job as coach is to have the client see the possibility of a condition-less reality and get them in touch with it. NOT to put them there and keep them there permanently. Because condition-less-ness cannot be obtained, it can only be practiced.


Just like condition-less-ness, coaching mastery can’t be obtained, it can only be practiced. One of the best tools we’ve found for practicing our own coaching is the Coaching Canvas. Actually, we didn’t find it… we had to make it ourselves. We designed the Coaching Canvas as a tool to deconstruct the world’s best coaching conversations, and to learn from them.

That original creation was totally selfishly motivated—we needed a tool, and we couldn’t find one already built. So we made it ourselves. And now we’re sharing it with all of you. Get your copy here.

You only need to care about the DROP if you want to be a great coach

Most coaches don’t need to worry about the Drop. Not because the Drop doesn’t happen in a coaching conversation. But because the Drop is built in to their model of coaching.

But if you want to be a great coach—a coach who has a bigger impact than most, who makes more money than most, who changes lives like most coaches ever could—your life needs to become about the Drop.


If you look at Byron Katie’s “The Work” question: “Is it true?”, or Rich Litvin’s question: “What would make this an extraordinary conversation?”, you can see that the Drop is built in.

For Katie the Drop is chosen by the statement. That’s it. The statement doesn’t matter. Your Drop is to examine the truth of this statement. It’s simple and predictable. For Rich it’s no different. His question creates a certain kind of Drop. The Drop is your dreams. Tell me about them. You can have them now.

Of course Rich’s questions is broader so it doesn’t always work, but it often does because it is a Drop creator. Which is why if you’re like most coaches—the average coach, the mediocre coach, even the good coach—you don’t need to worry about the Drop, because you’ll get to something. It’s just built in to the way you show up as a coach.

Because in all of the coaching conversations I’ve ever watched, consistently, repeatedly, the Drop is the fundamental foundation of all the magic that comes before and after.

The Drop is the pivot point of great coaching and it’s NOT something you should leave to chance or formula. It’s something to be mastered, studied, and practiced.

But of course you’ll never realize this if you don’t practice it and discover this for yourself. So that’s what I’m going to help you do right now.


The Drop is the place where the coach and client “drop into a pocket of coaching.” It’s the place where the coach and client choose or dive into a particular area of focus. It’s. . . you know, the Drop is hard to describe, actually.

Kind of like that old saying about pornography: “It’s hard to define, but I know it when I see it.” The Drop is like that.

When I watch a coaching conversation with a brilliant Drop, I can see it. Sometimes I can’t see it until after it’s happened, but even then I can feel it.

In a bad conversation it’s ALWAYS missing. And I mean always.

The reason? When a coach rushes to GET ON WITH THE COACHING, they very often miss the Drop entirely. They just start coaching on something. And it sort of works. Because, well, you can coach on pretty much anything. But just because you can coach on anything doesn’t mean that you should.

On the other hand, when a coach finds a Drop, all of a sudden the conversation becomes ABOUT SOMETHING!!! Ideally it becomes about what the client wants. But more than anything the Drop is about moving from the conversation being about ANYTHING to being about SOMETHING.

Mediocre coaching can be about anything. GREAT COACHING IS ABOUT SOMETHING.

So you should only care about the Drop if you want you coaching to be about something. Which is why your practice assignment for today, if you choose to accept it, is this:

During and/or after every coaching conversation this week ask yourself this question:


If you can’t answer the question easily, or if you realize YOU can answer it but your client can’t, it may be that you didn’t create a Drop. So just notice that and wonder: what might change if my coaching conversations were ABOUT something, instead of about ANYTHING?


If you are the kind of coach who wants to care about the Drop, who wants to have coaching conversations, who wants to be GREAT—and is willing to study and practice to get there, download your copy of the Coaching Canvas today.

The #1 Coaching Blindspot

What amazes me about coaching mastery isn’t the complexity of the blindspots coaches have, but the simplicity of them.

You would think since the Dojo is made up of brilliantly clever coaches with experience ranging from 3 to 10 years, that the ways in which coaches shoot themselves in the foot would be vast and numerous. But in truth, the #1 blindspot I see over and over again is the same simple one and today I’m going to tell you how to avoid it.

Okay, so you’re probably wondering if I’m going to string you along and build up the tension of what this one thing is. No, I’m not going to do that. So here it is:

The #1 blindspot coaches have is . . . THEY DON’T FIND OUT WHAT THEIR CLIENTS WANT.

I know you’re probably thinking you don’t do this, and I get that. For the first two weeks of the Dojo we pretty much repeat this advice constantly. We watch someone coach and then we tell them.

That was great, this question was brilliant, and I loved your presence AND the biggest opportunity I saw was that you didn’t find out what the client wanted.

I can’t even tell you how many times I’ve said it, but coaches continue to struggle with this for a very simple reason. Coaches love to coach.

And so because we’re busy rubbing our hands so that we can get in there and change their lives we forget something very simple and very important.

What about their lives do they want to be different?

We forget this because we see possibility for them, deep powerful and incredible possibility, but possibility is just that, one of many possible things.

Think about it this way. Lots of parents have babies (in fact, it’s the thing that makes them parents). And as they look at those babies they see possibility in them—the possibility of jobs, and sports trophies, and weddings. Some parents, when they look at their babies, see very specific kinds of possibility.

Some parents see the possibility of a doctor, others of a mother, others of a professional athlete. And even though this is one of many possibilities that are available to their child, the parent decides this is the one that should become a reality. And so they begin to suggest, nudge, cajole.

Sometimes they get what they want—perhaps at the cost of their children, or at the cost of authentic relationships with them. Sometimes they don’t get what they want, and instead get rebellious children who resent the various suggestions, manifested as a story about being pressured. Sometimes the stars align and the child’s desire matches their own. But when the last one happens, it’s almost always because at some point the parents give the power of choice to their children—the parents let the children choose what they want.

This is very much what it’s like to be a coach. Because as coaches we see so much and we convince ourselves we know people very well, we tend to see a very specific kind of possibility for people. This client is too shy, this client works too hard, this client is too easy going. And in this seeing we create a possibility for them to be different—and we, like proud parents with a baby client, begin to nudge, suggest, and cajole them into what we think they should want.

But this isn’t coaching, this is suggestive parenting. Of course it’s completely reasonable to see a possibility and offer it to them, like a parent offering a baseball bat as a toy. But to be clear about the line and the commitment to what the client wants is essential.

Which is why if you want to be a powerful coach, you must AND I MEAN MUST find out what the client wants before you begin to coach them.

And yet you probably will forget this.

You’ll forget this because in that next session you’ll see what’s possible and decide what they should want. And I’m asking that you not. I’m asking that in service of your deep and incredible mastery, you slow down. Take a breath and ask them.

“What would you like?”

Slow down and dig into what they want. Find out if that’s really it. Or if there’s something they think they’re going to get if they can buy a fur coat, change jobs, or break up with their boyfriend.

Slow down and really get on a very deep level what is it, this thing they truly, deeply and powerfully want.

This is the essence of the most vital part of a coaching conversation, the part we in the Dojo call the DROP. And doing this well, mastering how to DROP into the right pocket of coaching, is the difference between incredible sessions on the reg and mediocre sessions as a curse.

Okay, great. So I told you what to do… but you’re probably wondering HOW. “How do I do this?”

Not to worry. We’ll be talking about the DROP all month. Much more to come!


(And if you can’t wait that long, you can always check out our ODSC Framework series, which has an extensive section on the Drop, starting with this post.)

To do your own analysis of coaching conversations to identify the Drop, be sure to download your copy of the Coaching Canvas tool.

What Are the Best Questions to Ask to Start a Coaching Conversation?

NOTICE: Tomorrow we’re hosting a Micro-Dojo webinar called

Death to Zombie Coaching Sessions!
(How to prevent brain dead sessions that go nowhere)

In this session we’re going to:

  • break down how Master Coaches start their coaching sessions,
  • talk about the most common mistakes that cost coaches clients and impact, and
  • help you learn how to create powerful openings that prevent your sessions from dying a death of Zombie mediocrity.

Today is the last day to register, so if you want to learn how to start you sessions like a master coach, register here:

Okay, now on to today’s post: What are the best questions to ask to start a coaching conversation?

Bruce Lee once said, “I fear not the man who has practiced 10,000 kicks once, but I fear the man who had practiced one kick 10,000 times.”

If he had been a coach, he might have said, “I fear not the man who has practiced 10,000 questions once, but I fear the man who had practiced one question 10,000 times.”

And yet, if you do a Google search on coaching, you’ll soon begin to think that coaching is all about developing an arsenal of questions. You might even imagine that the world’s best coaches are the ones who have spent the longest time in a sort of “question arms race” and need to sign question non-proliferation treaties. But this isn’t the case.

Knowing a lot of questions is grand, but knowing why they work and when to use them matters even more. For a minute I’m going to ignore that advice and pretend to be BuzzFeed and give you my top 3 opening questions. But just so I’m a little more like Bruce Lee, I’m also going to explain to you exactly why they work—so you can see that while the questions are good ones, it’s the impact of these questions that matter. Which I why, though I ask them again and again, I never just rely on asking them without any attention or awareness.

Question 1: How are you doing today?

When to use it:

Whenever you get on the phone with a prospect or new client. Whenever you get on the phone with an existing client and you can sense something different in their energy. Whenever you meet your neighbor on the elevator, and you can’t remember their name, but you don’t want to stand there silently.

How it works:

It helps creates two things at once. The first is Rapport, which I’ve talked about before. It’s an easy question to answer and it also gives your client a chance to tell you how they are and what’s going on for them. The next thing it does is sets some Context. What is your client coming into this conversation with? What’s been going on for them? Has anything changed since you last talked that may have an impact on the session?

What to watch out for:

Be careful if the client dodges the question or goes on a lengthy diatribe. It may be they are trying to ignore or deny something that’s weighing on them, or it may be that they are trying to avoid the vulnerability of the coaching container.

If you want to go deeper:

You might try asking, “Can you tell me a little bit about what you day has been like before our conversation?” This is a more specific question and directs the client to look more at the energy of what they’re bringing to the coaching conversation.

Question 2: I’d like to just BE with you for a minute. Is that okay?

(Variations include: Would you mind if we did a little mediation together? I’d like to take a few deep breaths with you; is that okay? I’d like to just close our eyes for a minute and breathe; is that okay?)

When to use it:

As soon as you’ve built a little rapport with the client and you can feel you’re both ready to transition into the conversation. You can use this either before or after you set a context or agreements for the conversation and before or after you choose a focus for your coaching. It also works great whenever you need to reset or go from one topic to another, especially if the previous topic was heavy or fraught in any way.

How it works:

It sets an energetic context and brings both you and the client into the room in a powerful way. It also serves as a clear transition from the regular world into the world of the coaching conversation. It also helps you, as coach, to get grounded and present. And finally, if done right, it creates a sense of awe which prepares the client to do deep, powerful work.

What to watch out for:

Make sure this doesn’t just become a rote exercise you do because you’re supposed to or something you’re just doing for your client, because it can be powerful for both of you if you actually use it to get grounded and connected with your client.

If you want to go deeper:

Use this meditation to set a powerful context for the client and/or allow your heart and their heart to open up. While coaches often practice and learn opening steps they often forget about the power of opening energy. Master coaches never make this mistake—they use their energy as much as their questions to open up a powerful conversation.

Question 3: What do you want to talk about today?

(Variations include: What would you like to get out of our conversation today? What would you like create during our conversation today? What would you coach around today? What would you like to get out of our conversation today? What would make this an extraordinary conversation?)

When to use it:

After you’ve built rapport, gotten grounded and are ready to dive into the session. Ideally this question should come within 10 – 15 mins of the start of the conversation. After watching hundreds of coaches coach, I can say with a fair amount of confidence the #1 reason coaching sessions go nowhere, wander around aimlessly, or are unsatisfying is because the coach never really discerns what the client wants.

Too many coaches think that a conversation will just DROP (find a focus) on its own, even though this is almost never the case. Which is why if you do NOTHING ELSE in a coaching session you should USE THIS QUESTION AND GET AN ANSWER. Doing so may be the difference between the life and death of your coaching session.

How it works:

It asks the client to set the context for the coaching conversation. Often clients don’t know exactly what to get coaching around, but this at least helps the coach figure out what subjects are available and begins to move a coach from the OPEN phase to the DROP phase of the conversation. While this question won’t clarify what a coach should DROP or focus/coach on, it does give the client a chance to ask for what they want.

What to watch out for:

Clients love to not answer this question. They will ramble about their day, refuse to choose a subject matter, say they have nothing to coach around, or do something else to avoid choosing an area of focus. Sometimes it’s because clients don’t know what they want support around, but often it’s because clients are unconsciously avoiding the things they know they need to look at in order to move forward.

This is why it’s essential—and I mean ESSENTIAL—to make sure you don’t advance beyond this stage without finding out something—anything—the client wants, even if what the client wants is to know what to have the conversation around. Again, 90% of the bad or mediocre coaching sessions I’ve watched end up being much less than they could be because the coach doesn’t find out what the client wants.

If you have a more open or intuitive style that’s fine. Start by finding out what they want and let go of the structure and explore freely after that. Wandering in search of a lost artifact can be powerful, wandering in search of your own tail much less so.

If you want to go deeper ask:

You might try asking: “What would having that do for you?” and/or “And what might you lose that you value when you can have what you want?”

Both of these questions come from the NLP Marin lineage. I’m loathe to explain the reason why they work, nor would I say that using them serves a solid substitute for learning the NLP Marin method called Transformational NLP. But these questions can still be powerful no matter who uses them.

The reason is simple: when we only pay attention to the peak we often miss motivation or other key areas of the terrain around a desire. When we can help our clients understand the underlying motivations of a desire, as well as what’s at stake in our pursuit of it, a lot of things become possible that previously weren’t.


That’s it! Three simple, powerful questions to help you start any coaching conversation the way some of the best coaches in the world do. In fact, the more I watch truly masterful coaches, the more I see and realize just how good they are at making very simple questions do incredible things.

If you want to do work that matters, change your clients’ lives, and make a bounty of treasure by helping them create incredible futures, don’t practice 10,000 questions once, but a few questions 10,000 times.


How to Open (i.e., Being Human with Other Humans)

(a guest post by Sensei Bay LeBlanc Quiney)

Hey you! Nice work, getting into connection with a potential client! That’s awesome! Someone asked you for a conversation of possibility, or you invited them, and they said yes.

Seriously, that’s no small thing when your entire business depends on your ability to create connection and turn it into conversations.

Have you ever noticed though, that once you start getting those conversations on the calendar, you also start to get a little weird about them? Maybe you start wondering what you’ll talk about, or what you should say to get them to be a yes to your fees. Maybe you think about what you could say that would create instant insight and demonstrate your incredible prowess as a coach/Powerful Transformer of Human Potential. Maybe you start wondering what might be their issues or concerns, or how they’ll say no to your offer.

The problem lies in this thinking part—and specifically, the thinking-too-much part—especially when it comes to how you can do this right.

“Now, Bay,” you say knowingly, or perhaps even a bit smugly, “there isn’t any right way to do this.”

Correct. But even though you know there’s no such thing as the right way, you still want to do it right, and by “doing it right” we know you mean that you want this conversation to be successful, and go the way you want it to go, and obviously result in a yes to your proposal.

There may not be a right way, but I’m pretty sure I’m right about that last part, yeah?

I mean, sure, you talk to humans all the time, but this human might be a potential client, and you want some of those, of course. Now you’re wondering how to not be too needy or too eager, but also play it cool—but not too cool, right?

It’s not unlike trying to have a normal human conversation with that person you had a crush on in high school, only to discover your tongue/brain suddenly went into a strange paralysis when the opportunity actually presents itself and you’re face to face with the object of your affections. Suddenly, you don’t know where to start, or what to say: I could’ve sworn I knew words?

It’s one of those great mysteries of life—we often create an inability to successfully execute an action we do all the time, as soon as we stop and try to think over it too much.

So in support of you not overthinking an opportunity to step up to the plate and play for your desired outcomes, I’ve put together a few thoughts on how you can practice having great conversations of possibility with humans (even of the potential-client variety) that are enjoyable and satisfying for you. Because if you’re going to build a business upon conversations, it matters that you have a good time with it.

1. Don’t be a weirdo—slow down and build some rapport.

I know. It’s so tempting to jump straight to the quick and see if you can spontaneously generate a breakthrough for the person across from you. After all, you can see their obstacles and blind spots and limiting beliefs, right? Bonus points if they cry?

(Seriously though—please don’t play that game. Coaching is not baseball; you don’t need to hit a home run, and while crying/emotional distress may occur, it is not a goalpost.)

The thing is, since there’s a real live human across from you, it might be nice to say “Hi, how are ya?” before diving headfirst into someone’s deepest desires and fears.

This person has overcome at least a certain amount of fear or discomfort to say yes to this conversation with you. What do you know about them? How are you going to find out? What do they know about you? How will they know they can trust you, or relate to you?

Have you ever been approached by a salesperson in any kind of business, and known that to them, you were just a potential commission? Or had someone offer you a solution before they bothered to uncover your problems or needs? It’s gross, right? Or at least off-putting?

Don’t off-put people when you want to connect with them. Instead ask them questions and let them ask you questions, too. What do they want to know about you? What would be important for them to understand about you, as a fellow human?

Rapport is about slowing down and spending time getting to know who is on the other end of the conversation. What matters to them, their background, where are they from, etc. So spend AT LEAST five to ten minutes meeting this person, and get interested in them.

This isn’t useless information, by the way. This is solid gold. It’s where you can start to listen for the context of their world, and understand where they’re coming from. You know, so you can coach them on it and maybe even get clear on what would inspire them to commit.

2. It’s not about you.

This conversation? It’s not about you. It’s not about what a great coach you are, or how good you are at selling programs, or solving people’s problems.

This conversation that you’re in is all about whoever is across from you, whether that’s in person, on the phone, or on a computer screen. Her hopes and impossible dreams. His future. Listen to the person across from you, and hear what is said, what is unsaid.

If you’ve been thinking about where to take the conversation, then it’s not a conversation in the realm of possibility; it’s a conversation in the world of predictability. What’s worse, it’s not even their world of predictability: it’s YOURS, including all of your preconceived limits and ideas.

If you’re trying to figure out where to go in the conversation, you’re not listening to them; you’re making it about you and what you want (to do, to get, etc.). The person across from you will know it, too, even if they don’t know that’s what you’re doing. You can feel that vibe a mile away, and it tends to close more doors than it opens.

If you’re really listening, you’ll likely become curious about what you hear and learn. But curiosity only shows up if we allow ourselves to play in the realm of not knowing.

3. Don’t think; dance.

You’re not playing sheet music here. You’re dancing with a partner who may not know the steps. Maybe they’ve never even danced. It’s up to you to take the lead initially, and then let go and move with the music. It’s an improvised game—but even in improv, someone has to know the game for the magic to happen.

This may sound counterproductive to my earlier points, but I promise you it isn’t. Remember, you’re the coach. This person you’re talking to? It’s possible she has never talked to a coach before. That means she may have no idea what to expect, or what to do.

She may need some support in understanding where you two will go in this conversation, or what a coaching request is, let alone what she’s responsible for in this session. She may not even understand what coaching really is, or how it differs from, say consulting or therapy.

Be willing to provide a general direction for the journey ahead, so that you can then lean back and let the client take the lead.

4. Be present.

Honestly, if you were to take on practicing only one of these points, this one is the gold standard. If you practice being present in your conversations with potential clients, all of the above will usually resolve itself.

So, take a deep breath. Your only job is to be here, with this person, right where you both are. You’re in this conversation together, so why not chill out, and just be with this human across from you?

In this moment, you’ll know where to go, because the moment you were in just before will inform you. This means you don’t need to worry about whether he’ll hire you at the end of this session, or two more, or if she can afford your rates.

To sum up, if you’re looking at how to open a conversation for possibility, you may want to consider just being your plain old open self. This means being willing to let go the reins, and trust the conversation to go where it will best serve going.

If you didn’t have to focus on how to serve this person best, but you could just relax and BE you, in this moment, inviting this person to do the same, what might happen?

I know one way to find out…


PS: For other Open goodness, check out our recent mixtape series on the best questions to open a coaching conversation, plus our comprehensive ODSC series. And of course, the tool that’ll help you analyze all four phases of the coaching conversation, the Coaching Canvas, is available free to you.

Day 5 of How to Start a Coaching Conversation Like a Master Coach (The Mixtape):

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

Today our little OPEN phase series on how to start a coaching conversation like a master coach comes to an end, with my favorite question: “What would you like?”

I had to answer this question at the start of almost every single coaching conversation I had with my coach Jeff Riddle. Part OPEN phase question, part DROP question, I learned to love and hate it as client and as coach. But in learning why the question worked and how to use it, I also learned how to avoid the pitfall we see almost every single coach make when they first enter the Dojo…

Master Coaching Awesome OPENs Track / Question 5: What would you like? (Carl Bucheit)

Why it works: If you ask 100 coaches what the point of coaching is you’ll get 100 different answers, but when you boil those 100 answers down, you end up with a few simple concepts, central among them being Freedom. Our jobs as coaches is to help our clients get what they want. Of course sometimes they don’t really want what they say they want, but this is beside the point. It is almost impossible for a coach to do their work if they don’t know what the client wants.

And yet I can’t even tell you how many sessions I’ve watched where neither the coach nor the client knows what the client wants. Now don’t get me wrong. You can certainly sit in inquiry and discover desire. There’s a lot of coaching that’s very much this.

But at the end of the day I would bet that 90% of bad coaching is a coach and client wandering around inside a client’s mind without direction or a coach shoving a client through a system or process without really knowing what the client wants. And sort of like a computer if you put junk into the coaching process you tend to get junk out.

This is why this question is my favorite OPEN/DROP question of them all. It works on two simple principles:

  1. If you want to know what someone wants, ask them.
  2. We tend to add extra energy to words like want, need, crave, desire, but when we decide what we would like, we merge both the lean of desire with the softness of discernment.

This question takes the stance that life is like ordering off a menu. Anything is possible on the menu, we simply have to decide what we would like.

In addition it works so well because most people are great at telling people what they don’t want (stress, their partner to complain, 10 lbs of fat, etc.) but they are less good at saying what they actually do want.

This questions starts the client at the simple place of desire and asks them to choose. Of course the process doesn’t stop there. Jeff would often follow this question with questions like:

  • What would having that do for you?
  • What might you lose that you value when you can have what you want?
  • And what would having that do for you?

But “What do you want?” gets the ball rolling in a powerful and simple way.

Why I love it: Every single bad-to-mediocre coaching conversation I have ever watched would have been improved by the insertion of this simple question. A coach and client lost in the weeds can be returned to reality by the question, and a process gone deeply off the rails can be returned to the tracks with this question.

It is so simple and so foundational, and yet creates an opening wherever it goes. Providing of course that you actually get the client to answer the question, which at times might take entire sessions.

But the lightness of it embodies so much of what I love when I watch a master coaches. Watch any great performer. While it may be the flashy moves that stand out, it’s the complete mastery of the fundamentals that lies as foundation of their practice. And this question serves as a keystone of any master coach’s skill set.

How you can use it: Just start asking it at the beginning of the coaching conversation and don’t choose to create a DROP until you have an answer. If you are a new coach, I urge you to take on this practice as an absolute for 6 months to a year. It’s not that there aren’t naturally intuitive coaches that can skip over this step, it’s just that most people who claim they coach by intuition look more like they’re trying to bowl with bumpers, but someone put the rails down.

Of course any answer to this question won’t be complete, but it is a good place to start. As you deepen your practice you’ll learn to hold the tension of accepting and starting with what the client says they want, while also probing and discerning what the client actually wants.




If you loved it, I’d love if you comment on it, share it, or email me and tell me what you liked about it. If you’re confused by any of the points, please don’t hesitate to ask me some questions as well.

I also want to point out that the level of analysis I offered in these questions was only possible because I used the simple but powerful tools of the Coaching Canvas to study these master coaches. We created the Coaching Canvas to help coaches learn how to study, improvise, recreate, and vastly improve the way they coach. Get your free copy here.

If you want to learn more about how to make your coaching sessions as powerful as the world’s best and most successful coaches, on Tuesday, November 27, at 3pm Eastern, join us at the Micro-Dojo Webinar called:

Death to Zombie Coaching Sessions!
(How to prevent brain dead coaching sessions that go nowhere.)

If we were another kind of coaching course, I’d tell you about how it can also help you 10x your client results, impact, referrals, and the rates you charge, but in the Dojo we believe that masterful coaching pays for itself several times over, in deep enjoyment of doing work you love, and in incredible results that prospects and clients come back (and pay) for.

To save your spot (in the infinite number of available spots), click this magical bit of red text right here.

Day 4 of How to Start a Coaching Conversation Like a Master Coach (The Mixtape):

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

While part of me would love to spend this entire post talking about the simplicity of The Work as well as its limitations, for now we’re just going to look at the OPEN/DROP questions and why they work to open a session powerfully no matter the subject and how you can use their simplicity to know how to create possibility even when you feel out of your depth as a coach.

But first, some background…

Byron Katie’s The Work is one of the most systematic, and in some ways rigid, coaching or deep-work structures that exists. It’s also a very polarizing approach to deep work. Some people love the simplicity; others criticize it as a bit of a hammer in search of a nail, and that its community is a little too cult like for its own good. But opinions aside, I think there’s some real gold to be extracted from The Work, whether you use it as it was created or whether you just learn from the model it offers.

Part of the reason The Work, um… works? so well is that it contains all of the elements we see in every great coaching session.

Three powerful OPEN/DROP questions:

  • What statement/belief/thought would you like to work on?
  • Is it true?  
  • And can you absolutely know that it’s true?

Two simple but effective SHIFT questions:

  • How do you react, what happens, when you believe that thought?
  • Who would you be without that thought?

And a simple but effective CLOSE:

Which is achieved by ‘turning around’ each statement and experiencing the alternative view of  reality they offer.

And while each phase of The Work holds some magic, a bunch of that magic relies on the relativistic/Zen-like foundation of the Opening questions Katie crafted to start The Work.

Master Coaching Awesome OPENs Track / Question 4: Is it true? (Byron Katie)

Why it works: While many coaching models spend a great deal of time trying to figure out what to focus on in a coaching session, The Work employs an incredibly simple process that tosses that discernment to the wind.

This first question is both incredibly simple and powerful. It asks the client to “write down a stressful concept about someone (alive or dead) whom you haven’t forgiven 100 percent.”

(For example, “He doesn’t care about me.”)

This first question acts as a sort of indiscriminate, industrial, belief-sifting machine that won’t allow more than one belief through its chute at a time.

Once that statement is produced—”he doesn’t care about me”—this very same machine cleaves your resolute righteous from reality with a single chop with the question:

“Is it true?” (Yes or no. If no, move to Question 3.)

In some ways The Work could stop here. After all, with enough resourcefulness and perspective anyone can see that their strongly held beliefs are often poorly constructed, but BK knows that our beliefs and judgments are hardier that that.

Which is why question two follows question one for any statement that survives the first chop:

Question two is: “Can you absolutely know that it’s true?” (Yes or no.)

At this point almost no belief can survive unless the illusion is deep. This question in a way provides a full coaching cycle that shatters obstacles. It OPENs with a unit of belief, it chooses a DROP of absolute truth, it creates a SHIFT by cleaving belief from truth, and it CLOSEs by producing a shattered belief for integration.

The rest of the process in a way is all about having the client see the impact of having a certain belief and showing them what’s possible from different perspectives, but these OPEN questions are so powerful because they rest on a stance of absolute truth and the imperfection of human perception and thought.

This opening point itself is so powerful to have garnered The Work a nearly cult-like following of belief-cleaving practitioners.

Why I love it: I love the simplicity of The Work’s OPEN phase and how formulaic it is. I’ve watched new and experienced coaches alike grasp and crawl around for a subject coach around and The Work reveals just how simple and powerful an opening can be.

I also see the limitations of The Work in the same way I see the limitations of three principles work. In a way, both fall victim to the idea that Right View is enough for deep awakening. Perhaps with a side of Right Thinking. But when I look to the paths of awakening from the Buddha to the Christian Gnostics, I soon find that Right View and Thought are just two parts of the process and it’s because of this I don’t just do The Work with my clients.

And having said that, I can’t deny the raw power The Work offers and the glorious effectiveness of its opening. It’s something I often think about when I find myself struggling to find a solid OPEN or DROP with a client or prospect.

How you can use it: Again, you can use The Work out of the box. I don’t think it’s a panacea, but I learned a lot by taking clients through The Work. After a while it begins to feel a little paint-by-numbers and feels a little like being a Samurai behind a machine gun or a meat grinder.

But if you don’t want to follow the step by step you can rip out the architecture and use it free standing.

As you go into your OPEN and move into the DROP phase, notice what statements of belief the client is holding most dear. Sometimes these beliefs will be apparent: No one sees me. And sometimes they will be camouflaged. But before you move forward, write down a belief or two, especially the ones that either the client sees as most true or the ones you most want to buy into.

And there on your notepad ask: Is it true? Can you absolutely know that it’s true? (Yes or no.)

Once you’ve seen beyond the view of the world your client is trying to buy into you will be in a much better position to see what’s possible for the client and be much more likely to choose or guide a client into a powerful drop for your session.

And as with all of these things please go and practice them. You learn ideas by reading but you gain confidence through practice.


The next post will be the last one in this little series. And I’ll be looking at my favorite question of all: “What would you like?”

It’s a question I learned from my coach of two years, Jeff Riddle, which he learned from his teacher, Carl Bucheit. We’ll talk about why this is the only question that ever really matters and why most coaches who try to go deep forget to ask it.



PS: Remember, all of this analysis was made possible by this simple coaching tool we created called the Coaching Canvas. Get your free copy here:

PPS: And for more on great Opens and other coaching goodness, remember to sign up for our free Micro-Dojo webinar-class-teaching-thingy called

Death to Zombie Coaching Sessions!
(How to prevent brain-dead coaching sessions that go nowhere.)
Register now!!! 

PPPS: Enjoying this series? Please share the love with your fellow coaches and others who might benefit!

Day 3 of How to Start a Coaching Conversation Like a Master Coach (The Mixtape):

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

So far we’ve listened to the situational brilliance of Tony Robbins’s powerhouse hit (“What’s changed?”) and Rich Litvin’s classic (“What would make this an extraordinary conversation?”). And today we’re going to listen to Michael Neil’s Alt-Coach anthem: “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?”

And in learning why this question works, why I love it, and how you can use it, we’ll also look at how to challenge some fundamental assumptions many coaches and clients make, and how disrupting those assumptions can open up a trove of possibility and help you take your worst sessions and make them some of your best.

Master Coaching Awesome OPENs Track / Question 3What if you didn’t have to have a question? What if we both looked in a direction and saw what there was to see? (Michael Neil)

Why it works: I got this question from a Michael Neil YouTube video, which you can find here:

In the video, a woman is sitting on stage with Michael and says she doesn’t know why she’s up there. She doesn’t even really know what her question is.

And in an instant Michael accepts her premise and context and shifts it entirely by asking, “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?”

He extends this by using a metaphor of taking a stroll in a park and juxtaposes it with the idea that you’d have to have a specific purpose in mind for what you’re looking for on a stroll—which brings a moment of lightness and humor to the conversation.

The client believes she needs to know what to ask to get value out of the conversation. This belief is an assumption Michael undoes by offering an alternate reality; one in which coaching is more than having a question to answer.

And in shifting from one reality to the other he takes the resistance offered by the client, “I don’t know why I’m up here,” and turns it into an opportunity, “What if you didn’t have to know why you were up here?” And in that moment possibility is created.


Why I love it: Our clients often resist the truth or perspective we offer, but most coaches make the mistake of fighting or pushing against that truth.

And while directly challenging a truth can sometimes serve a client, often this action causes and even sharper and stronger reaction.

In contrast, with this OPEN Michael does a beautiful job of accepting the client’s resistance and then creating a larger context for the conversation.

This is an especially powerful example because it reveals that while most coaches have the ability to see and shift a client’s assumptions, a master coach has the ability to see and shift their own assumptions in service of the client or the flow of a session.

How you can use it: The easiest way to begin to use a question like this is to pull it out whenever a client comes to a session without anything to talk about. But as you do, be careful your stroll doesn’t turn into a madman’s ramble. Your job as coach is to follow your client until you can discern or guess what journey your client’s subconscious is wanting to take and then to offer a path to see if their conscious self would like to walk it.

In this conversation, Michael does this using more teaching than coaching, but what he doesn’t do is let the client wander and get lost with her.

But if you want to go deeper with the underlying skill of feng shui-ing client resistance, you can start by noticing how you respond to client resistance in your sessions. Try to take a few notes whenever you notice resistance (especially in the opening) and how you respond to it. Then once you’ve brought some awareness to this, see if you can accept the resistance and use the momentum of that resistance to create a sense of spaciousness.

Of course this takes time and practice. Going deeper on this by practicing with a sparring partner and getting feedback can be incredibly valuable for refining this ability, but just bringing awareness to it alone is a great place to start.


That’s it for this one. Tomorrow we’re going to cover Byron Katie’s super-famous opening question from The Work: “Is it true?” And talk about why it’s so effective and how you can use the power of this question even if you don’t love the system of The Work as BK offers it.


PS: Remember, all of this analysis was made possible by this simple coaching tool we created called the Coaching Canvas. Get your free copy here:

PPS: And for more on great Opens and other coaching goodness, remember to sign up for our free Micro-Dojo webinar-class-teaching-thingy called

Death to Zombie Coaching Sessions!
(How to prevent brain-dead coaching sessions that go nowhere.)
Register now!!! 

PPPS: Enjoying this series? Please share the love with your fellow coaches and others who might benefit!

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

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

Death to Zombie Coaching Sessions!
(How to prevent brain-dead coaching sessions that go nowhere.)
Register now!!! 

Before the internet seats run oooouuuuu… ooooohhhh right, internet seats are infinite… Okay, well… register anyway so you can ask your questions live. And so you don’t tell yourself you’re going to watch the recording later, but you never do!!!