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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!!!

Day 1 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!

In the annals of coaching geekdom, I hope that someday there is a shrine to the total and utter dorky obsession that I have offered to the study of master coaches. I’ve spent hours watching sessions of some of the world’s best and best-known coaches, including Tony Robbins, Rich Litvin, Michael Neil, Byron Katie and plenty of others.

And while I collected a lot of questions and learned their RCFs (resting coach faces) pretty well, it wasn’t until I started putting them through the Coaching Canvas* that I started to realize this simple magic of their opening gambits.

Like a chess student finally realizing the brilliance of Bobby Fischer’s first few moves in a game, I started to discover how the world’s best coaches use simple questions to create incredible sessions and how to begin to use those same moves myself with my clients.

Over the next few days I’m going to be offering my Coaching Session Starter Mixtape, which is a compilation of four of my favorite opening questions by some of the coaches I’ve spent the most time studying. In each post I’ll explain why they work so well, what I love about them, and how you can use them with your clients starting tomorrow (or even today) to make every conversation from here on out much better than it was before.

Master Coaching Awesome OPENs Track / Question 1: What’s changed? (Tony Robbins)

To watch this question in action check out this YouTube video of Tony coaching a man at a Tony Robbins event:

Why it works: The client in this video is talking about how unhappy he is in his marriage and how he doesn’t want to go home and tell his wife he wants a divorce.

Tony discerns quickly from context that at some point this man loved his wife and was happy. Some coaches might be reluctant to take this leap, spending laborious minutes hearing about when he was last happy with his wife and getting tangled in a web of meaningless details.

Tony, a master at quick OPENs and DROPs at his events, instead cuts through that milieu and simply asks, “What’s changed?” In this question we can learn so much. If the man says nothing has changed we can learn that he’s unaware of the change or that he is aware something has changed. We can learn if he’s always been unhappy or if this unhappiness has a more recent cause. And most of all, Tony asks the client to tap into his own deep understanding of the situation and where Tony needs to focus the rest of the conversation.

Why I love it: This question gets so much done in the context of this conversation. This question in many ways serves both to open the context of the conversation as well as provide and entry point to the DROP Tony takes him into a few minutes later.

Perhaps the reason why I love it is the speed with which it is effective. Sometimes powerful coaching needs time and space, but often coaches use time and space because they think that’s “how it’s done,” when in reality master coaches get twice as much done in half the time by creating and using simple powerful questions that reveal lots of information at once. Also, I love that Tony is trusting his instincts here. He discerns something has changed, he guesses this guy has the answer, he directs his attention away from complaining to the situation’s larger context. All of this is possible because Tony has a hunch.

So often coaches have this idea that they shouldn’t have a hunch, but if you study the world’s best coaches, their BRILLIANCE comes from both the power of their hunch as well as their ability to offer that hunch in an unattached way. This is on display in a powerful way in this session.

How you can use it: To me this is the essence of master coaching. Whether delivered in Tony’s high-powered style or in a more gentle way, a simple question like this can reveal a lot. To use this kind of question, begin to record your hunches of what’s going on with a client as they talk and then try asking a questions that confirms or denies that hunch.

As you do this, make sure you don’t diagnose or prescribe an insight, keep your hunch a hunch, and like a scientist test your hypothesis and be ready to abandon it if the experiment yields conflicting data.

As you do remember the natural progression of hunches towards mastery:

  1. Clouded idea of what clients need to hear
  2. Realization you have no idea what clients need to hear
  3. Practice with not having ideas and just asking questions
  4. Starting to have insights about where sessions need to go
  5. Reluctance to go back to level 1 and trying to get clients to guess the answer you know
  6. Learning to offer hunches in a blurting way
  7. Learning to offer hunches in a gentle way
  8. Learning to offer hunches through skillful question experiments
  9. Rescue the princess from the bowser coaching castle


Okay, that’s it for today – don’t forget to tune in tomorrow where we’ll be listening to the classic and powerful “What would make this an extraordinary conversation?” used to great effect by my friend and former mentor, Rich Litvin.


* If you haven’t downloaded your own copy of the Coaching Canvas, what are you waiting for? Get yours today:

** Special thanks to Adam Quiney, Bay Leblanc Quiney, Christina Berkley, Kendra Cunov, Ken Blackman, David Burns, and most of all Christina Salerno (with whom I created the Coaching Canvas) for your insights and clarity that have and continue to help me improve my understanding of truly great coaching.

How Should I Start a Coaching Conversation?

Every coaching conversation that ever was had to start somewhere. Whether it was a life-altering session that changed the course of human history or the worst conversation any coach has ever had, all conversations have to start.

So how in the hell are you supposed to figure how to start it?

When I was a new coach, I loved being in the mix of a powerful conversation. I could feel my clients getting insights and new understandings, I could feel the next question on my lips, but at times starting a coaching session felt a little like starting a make-out session. Polite but awkward conversation, tentative advances and subtle cues, and a fair degree of uncertainty and self-consciousness.

Once I got some experience under my belt I noticed that my OPENs started coming from a different place. I would ask the same question again and wait for a response. And while the question got things started, I felt a little like the husband in a stagnant old marriage taking my boxers off for our tried-and-true Sunday night ‘whoopie-making’ session.

Which is why whenever I think about the question of how to start a coaching session I try to think about what can make a coaching session both simple and direct, but also powerful and unique. Which is why in my OPENs I always try to include three key elements:

1. Rapport: Before you are coach and client, you are person and person (unless of course you are coaching an alien, in which case you are person and xorlax). So first be a person; ask them how they are, share a little about yourself. This shouldn’t be very much of the conversation and notice the tendency to stay here too long. But building rapport is essential—especially if this is a new client or your first conversation.

While you may abhor small talk, these social pleasantries get a lot done in a short period of time.

  • Comfort. Since we know how to answer social questions, we feel more at ease and can dust off the rust of our conversational mind.
  • Connection. We use these simple questions and curiosities to connect with lots of people so there is a nice neutral groove that helps us get connected quickly.
  • Transition. These rapport-building questions can stand as a transition from whatever was before into the space of a conversation.

2. Context: Once you’ve gotten that out of the way you need to set some context. If this is the first time you’ve coached someone you can do this by creating a set of simple agreements. The ones I’ve used for a long time are:

  • Anything is possible. In your regular life there are rules about what’s possible; for the next hour can we suspend those rules?
  • Radical honesty. In most of life we aren’t honest because it’s dangerous, so let’s agree to be honest with one another—you about what’s really going on, and me about what I really see.
  • I do deep work, but you control the depth. Some coaches coach on the surface, but I love to work on the physics that dictate your world, so I’ll go as deep as you want and you can always say, “Hey, can we go deeper here,” or “Hey, can we slow down.”
  • 200% responsibility. In most of life we take 50% responsibility, and then if the other person doesn’t meet us we drop to 40% responsibility or lower. In this conversation you’ll agree to get what you want even if I ask the dumbest questions in the world. And I’ll agree to treat you like your life changing breakthrough is a question away even if you show up incredibly resistant.

These agreements—which I’ve adapted and adopted from conversations I’ve had with Christina Berkley, Rich Litvin, and more—are powerful because they set a simple but impactful context for coaching. They set a context of possibility, depth, honesty, and responsibility. Without expressing these contexts it’s very likely that my clients and I will default to a context of fear, doubt, protection, and safe betting.

Of course I don’t use agreements for every conversation, but I do make sure that we have a powerful context, either an existing context from previous coaching or one created in the moment.

3. Presence / Awe: Michael Neil offers a simple model of coaching in two steps: (1) Show up, and (2) Respond to what shows up. And even though this model is incredibly simple it’s also powerful because in many ways nothing is more powerful in the opening of a conversation than to be really present with our clients.

For most of our lives people aren’t really present with us. They are self-conscious, distracted, and set on their own agenda. So just being willing to be really present with your clients is a deeply powerful gift. Developing this ability through meditation and concentration practices can help but you also have to deploy that ability for it to be effective.

Often new and even experienced coaches are so worried about doing a good job that they forget to deploy their presence with their clients. Which is why many great coaches start sessions with deep breathing or a mini-meditation as a way to get both themselves and their clients really present with one another.

Even more so, masterful coaches actually generate a palpable space of awe around their coaching. Some do it with their deep presence and their being, some using the environment of the coaching experience, and some using meditations, incantations, or agreements that evoke a sense of awe for the entire session.

In some way the goals of all three of these elements are the same. The same as in any ritual that shifts us from our everyday life to something different, more magical.

I remember recently on a trip to San Francisco a friend and myself stepped inside a cathedral we were walking by. And almost immediately something changed. The air inside was still. People talked quietly or whispered to one another. The light coming through the stained glass shaped the energy into one of mystery and magic. The arches and height of the ceiling spoke to the work, planning, and craft that went into creating this building.

The creators of cathedrals understood well that in creating a sanctuary they needed to offer an experience that asked humans to step out of the mundane and into the divine. And that’s what you’re doing when you start a coaching conversation.

You meet your clients at the entrance of the temple in the midst of their human lives, you walk with them through the arches and doors as they move from the ordinary to the extraordinary and then you sit with them quietly as they are drawn into the chamber of divinity and have their inner selves prepared and quieted to be touched by something beyond themselves.

So if you want to start you coaching sessions powerfully you must learn the simple but powerful process of crafting a powerful OPEN, and learn how to use these powerful elements so that you know what you’re doing and at the same time it still feels like you’re doing it for the first time.

Why Coaches Suck at Explaining What They Do

Or, oral marketing as explained through a metaphor about boxes of cereal…

As coaches, we see the universality of all problems.

People think the challenge is in the content, in the people in their lives, in the details of their situation. But we know that’s not the truth.

We understand that most problems are problems of perspective, beliefs, and context. With the right view of reality anything becomes possible and with the right action in alignment with this view, fulfillment becomes realized.

But when people ask us what we do, we talk in this vague, universal language.

Who do you help?

OH, I help people who are held back by limiting beliefs.

OH, I help people who feel like there’s got to be something more to life.

Oh, I help visionaries who are up to something big in the world.

You’ve basically just described everybody.

Everyone is held back by limiting beliefs—it’s just that some people are more aware of a certain layer of beliefs than others.

Everyone feels that there’s got to be something more to life—it’s just that some of them are better at hiding behind a glass of wine at night.

Everybody is a visionary—it’s just that some people’s vision is a stable job and a couple of kids.

Because we see problems as universal and solutions as universal we tend to describe what we do in universal terms.

Then there are the other people—the niche people.

These are the people that say you should choose an arbitrary group and just learn to squeeze the infinite possibility into how you help construction companies sell more concrete.

Now for some of these people, they are truly called to serve their niche. They have experienced the pains of running a laundromat and want to help other owners.

But I’d say 90% of the people who “niche” do so more out of expediency than self-discovery. They have no idea what to do, but someone said you needed a niche so gal dern it I’M GONNA GIT ONE!!!!

It’s why so many niches seem artificial and feel fake. It’s not that the advice is bad; it’s just that it leaves out the infinite nature of deep work.

Luckily there’s a middle path—a way to do some sort of both. This is the path the Prosperous Coach walks 60% down, which is to not niche but to be in the discovery of your people.

Through coaching practice and feedback you can begin to learn who you are and who your people are. The people you love serving and who you feel called to serve. Not out of fear or necessity but out of curiosity.

Sounds kind of coach-like, right?

And then over time, you learn to understand how your people see the problem and how they frame the value of the ways they like to solve that problem.

Then over time, you begin to narrow yourself and define yourself by the person who has put the universe into a certain box of cereal.

The box of cereal that has the pictures and images your people are drawn to.

The box of cereal who advertises the prize they want.

And has ingredients they aren’t allergic to.

And on the inside, you know when you walk down the aisle that ALL cereal is essentially grain and sugar.

That the problems are beliefs and ways of being, primarily…
and practice and commitment secondarily…
and action, tactics, and doing tertiarily.

But you also know you need the box it’s in because your people will buy the cereal that’s in this box.

Your people can only see infinite possibility on the aisle if you learn to see the infinite problems and express them in the same language as their finite complaints.

This is the magic of coaching and marketing combined.

Selling water by the river because some people can only find a way to see and drink water once it’s in a blue cup.

This is the art of a master samurai coach.

So stop pretending that explaining the infinite is any explanation at all and learn to make cereal boxes in your backyard. So you can test them out. And so you can—as you learn who you are as a coach—also learn how to express the tiny piece of infinity your people are most looking for.

After all, as a friend of mine from NLP Marin says:


The Delusion of Unattachment

Somewhere along the way, we got this idea that being unattached is a sort of perfect ideal we should pursue. When in truth, pretending to be unattached is the doorway to delusion.


Recently I was called out by a member of the Dojo because I joked that I didn’t want to give him a list of other coaches to work with, because I’d like to see him work with one of the Sensei in the Dojo.

And at first when he called me out I felt ashamed.

I thought: “Man, he’s right! I shouldn’t hold back names of other coaches. I shouldn’t even joke about it. I should be unattached.”

But then I realized this isn’t true.

It is never true that I am unattached to a client I’m trying to enroll.

When I like someone, when I spend time with them, when I create possibility with them, I become attached.

I become attached because I’m enrolled in them, their being, and what I see for them.

When I serve a beautiful I enjoy being with, who’s thoughts inspire me, I WANT THEM AS A CLIENT, on no uncertain terms.


Acknowledging this attachment doesn’t make me an awful coach or doomed in enrollment. Rather, it makes me human.

A phrase I hear a lot is: NEEDY IS CREEPY

Which is true.

But needy and wanty are not the same things.

I want to sign my clients, I want to work with them, I want them to hire me over another coach, sometimes I want that even if I wonder if another coach might be better for them.


I pause for a moment and wonder, “Could another coach be better for them?”

I do this because I love my clients and because I know I’m not perfect, because I know that I am of the nature to become attached and at some points that attachment will lead me to act against my client’s own possibility.

But this knowledge doesn’t mean that I’m being unethical or being a “bad” coach.

I WOULD NEVER want to work with a coach who didn’t want to work with me, who didn’t salivate a little bit at the idea of getting inside my life and mucking around.

I would also never want to work with a coach who let that want get out of hand and pinned their ego on signing me up.

Nor would I want to work with a coach who was under the delusion of unattachment. Who believed that not even letting themselves want a client was the “right” way to be.

I believe our clients want us to want them. They want us to desire and crave their possibility. I think as coaches we should aspire and stoke this desire whenever possible.

I also think we should acknowledge our innate attachment so we don’t become ruled by it.

After all, the reason I said what I said as a joke was because I was and remain willing to share the names of other coaches.

  • I’m willing to tell a prospect they shouldn’t hire me, even if I want them to.
  • I’m willing to tell a client our relationship had broken down and we should stop working together, even if I want to keep working with them.
  • I’m even willing to tell a prospect No even if we both really want to work together, but I’m clear it wouldn’t serve them.

I’m willing to do these things because for me the practice of being a master coach isn’t one of becoming drunk on my own delusion of unattachment. But rather one of acknowledging that I am of the nature to be attached and allowing that attachment to serve me and my clients—right up until the point where it stops.

It’s the practice of being both humble and unapologetic of my humanity. And also of learning to step from a wisdom that includes the truth—without losing sight of what it means to serve the incredible possibility of the human being in front of me or the human being inside of me.