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Don’t Kill the Baby Chick of Possibility

The other day in our Facebook group I did a Live where I did a bit of coaching about the Drop with the coaches that showed up and asked questions. And in that process I created a little analogy that I think can help you have better coaching session as soon as you get it.

As you leave the Open and enter the Drop, imagine your client hands you a baby phoenix. This fluffy little phoenix chick represents their possibility. Your #1 job as a coach is to keep the chick alive. Easy enough, right?

Well, the thing I haven’t told you is that as soon as you enter the Drop, your client will try to get you to do things that will kill the chick. Mostly they won’t realize what they’re doing, they’ll simply being doing what they always do, since how we show up to coaching is how we show up to everything.

They might say, “HEY, let’s play overwhelm football! CATCH!!” #dead-phoenix

They might say, “HEY, let’s play it’s not my responsibility. Tag! YOU’RE IT!!” #dead-phoenix

They might say, “HEY, let’s play my problem is entirely practical and has nothing to do with my being boxing! DING DING!” #dead-phoenix

No matter what you do, no matter what they say, your job is to keep the phoenix chick alive.

And of course sometimes, maybe a lot at first, you’ll kill the chick. You’ll do it and not realize until later… and after the session you’ll find a limp little phoenix feather on the bottom of your shoe.

Luckily phoenixes come back to life (just like possibility), so you get another shot.

But in some ways 100% of the art of the Drop is keeping the phoenix chick alive and carefully, skillfully, having the client be present to it as well.

This is why practice, getting supported by a coach, and being in a community of transformation is so important. Because baby phoenixes can be easy to kill.

If you want to get better at the Drop:

  1. Write down the top ways clients get you to kill their baby possibility
  2. Write down what you need to remember, or be present to, so you don’t forget the precious thing you hold in your hands as a coach.


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The 3 Kinds of Shitty Coaching You’re Probably Doing

(OH, they start in the Drop BTW because #series)

You got into coaching because you wanted to help people. On some level this desire was deeply noble. You care about humanity, you care about other people, and you realize that your life means more than moving pixels from one column to another or creating tweets about deodorant all day long.

Of course, deodorant does have a noble background and history… and you can create anything to have a purpose, but I think you get my point.

So there you are, ready to go out and help people, except you’re not really sure how to do it. So maybe you read some books about how to help people, or you take a course. Or maybe you try to help people in the same way someone helped you. (A lot of people who end up coaches start because they got coached by someone.)

As the fog of your idealism wears off, you start to wonder if you’re doing this the “right way.” And so you read more books, you take a course that’s got words like “200 hours,” “proven system,” and “complete in four weeks” on the sales page, or you hire fancier, more expensive coaches and try to do what they do.

At some point you decide you’re good enough. You stop thinking much about coaching, and instead you start worrying a lot about marketing, niches, sales conversations, and signature programs.

Unfortunately this usually happens before you’ve gotten really good at coaching. In fact, very often you’re barely above mediocre. The impact? At some point your business gets stuck. You can’t sign clients above a certain fee, you can’t sign clients that aren’t in some level of crisis, or you can’t make enough money to do anything but barely scrape by (and that last one is only true if you’re really lucky).

Of course crappy coaching is only one reason why this might be the case. Sales and marketing can certainly have something to do with it, but it’s just as likely, if not more likely, that you’re coaching just isn’t that great.

Except since 99.9% of the stuff in the coaching industry is about sales, marketing, niches, six-or-seven-figure programs, money mindset, and being a wealthy walrus, you probably won’t notice.

After all, it’s WAY easier to sell you on the idea that a quick-fix funnel or social-media program will solve all of your problems, than it is to take you aside, put a hand on your shoulder and say, “Dude, you kind of suck at this coaching thing.”

Lucky for you, or maybe not, I’m here to help you not suck as a coach—or at least to come to grips with the way you suck as a coach.

But first some disclaimers:

1) The kinds/types of coaching I’m listing below are sometimes used by “successful” coaches.

I mean we hate to say it’s true but the truth is you can learn to sell something that sucks and still make money off of it.

Just look at lottery tickets. I mean the chances of winning are REALLY CRAPPY, but people still buy them.

Same thing with poorly made products. You’ve bought them, you’ve broken them, you’ve cursed at them, you’ve left angry one-star reviews on Amazon… AND YET, people still buy them.

In the coaching industry this is super easy to do.

Especially because it trades so much on persona, personality, and the perception of success, not to mention that coaching is really just a mashed up set of soft skills that are ill-defined, hard to measure, and easy to fake if you don’t know a lot about it.

Add to all this that our industry as a whole is built on a flow and churn of endlessly new and idealistic coaches who don’t know ANYTHING about what they’re doing and with dollar signs and words like “work from anywhere” in their eyes… and what you have is a San-Francisco-gold-rush-level flow of hopeless, naive, new coaches willing to throw money at their dreams out of desperation and scarcity.

Which means that for the past five years and maybe for the next five you’ll be able to make a lot of money with great marketing and not much great coaching.

2) These kinds/types/styles of coaching can be effective under some circumstances.

I’m not much of a coaching purist. I think all of this never give advice, always draw the answer out of the client, never hold them accountable BS. . . is . . . well . . .  BS.

In truth almost ALL of the bad or mediocre coaching that exists in the world has its place. I mean even the “don’t have sex with your client” rule doesn’t apply to all the great coaches I know. (A story for another day.)

Which is why I want to be clear, I’m not saying these kinds/styles of coaching will get you sent to the halls of coaching hell, or even the halls of coaching purgatory. Though I do chuckle at the idea that there’s a realm of hell for coaching without permission. What I’m saying is that when you use these as your WHOLE way of coaching, you are doing yourself, your client, and the craft of coaching a great disservice. So please, please, PRETTY PLEASE, stop doing them, or at least do them 1/1000th as much as you’re doing them now.

Okay, now that the disclaimers are over, let me do a bit better job defining what I think makes great coaching, in as simple a way as possible:

Here are (some) of the qualities of great coaching:

  1. It causes the client to change.
  2. It’s aligned with the change the client wants.
  3. It’s empowering for the client.
  4. It affects both the client’s being as well as their doing.
  5. It uses an appropriate amount and type of force/manipulation to produce the above results.

If you check out the chart I made up below you’ll see that A LOT of coaching ends up either being ineffective or disempowering. And some coaching ends up being BOTH ineffective and disempowering.  

All of the examples of bad coaching that follow fall into either the orange or red quadrants. You may wonder how this happens. Basically it’s due to the fact that coaches tend to optimize for either ego, outcomes, or feeling.

Coaching that’s effective but disempowering does tend to create more immediate and obvious outcomes. I mean, having someone yell at you to do a pushup will get you to do pushups—at least so long as they are yelling at you.

Coaching that’s empowering but ineffective trades on the idea that mindset is everything and tends to blend in a lot of woo woo mumbo jumbo without actually creating a powerful container for change. The client feels good and the coach feels good, but they are both sort of ignoring the fact that they’ll wallpapered over the same BS that the client brought into the conversation.

The last category coaching that is both disempowering and ineffective happens because either:

  1. The coach lies to themselves and convinces the client that the reason the coaching doesn’t work is because of the client, often by pointing to people who were successful, even though those people only managed to be successful despite the coach or because the coach reminded them enough of some sort of dysfunctional parent in a way that made them co-dependently effective.
  2. The coach and client are kind of just polite with one another. The coach is afraid that the client will get offended, so doesn’t really challenge the client, and the client is afraid that it’s not working because they’re broken and so doesn’t really say anything to the coach about what is or isn’t working.

And of course all of this starts to happen in the Drop. And of course there are a BUNCH of different kinds of coaching that fall victim to these problems.

But here are the most common ones.


I could easily blame Tony Robbins for this kind of coaching. The reason people coach like this is that it works… sort of. I mean there is something really powerful about challenging clients to not hide from their commitments. A bunch of different schools of transformation use this, including Landmark (though EST used to be even more hardcore), and even several 12-step programs do this in one way or another.

The theory is that if you really hold people to what they say they’re going to do, remove all excuses, push them to see what’s truly possible they get an experience of themselves beyond the BS of excuses and lies.

Coaches who use this love it, because it’s sort of simple and makes the coach feel really powerful. I mean, who doesn’t love yelling at someone, right?! It’s also close to a powerful stance to take with a clients, so it seems like a good idea.

Where it starts:

This coaching tends to start in the Drop, because the Drop tends to be ALL ABOUT WHAT THE CLIENT ISN’T DOING, and the slow, deliberate deconstruction of all of their excuses, reasons, or objections to why they didn’t do what they committed to.

The problem with it:

The big problem with it is that it doesn’t really look at the thing behind the excuses, at least not as often as it might. It uses the club of extrinsic motivation to beat clients into submission. And while it can work because most of us were raised in schools that used extrinsic motivation to push us to conform, it doesn’t leave the client empowered.

Instead it subtly sows a message of, “I must need someone to yell at me to get off my lazy ass.” Now this doesn’t mean that you shouldn’t ever confront your clients, but in general this form of coaching is artless, lacks subtlety, and serves to boost the coach’s ego at the expense of the client’s.

It also should be noted that this type of coaching can happen even without yelling. It’s more of an energetic feeling than anything else.

If you notice yourself doing this more than two sessions in a row, please stop being a dick and try to figure out how to make your clients feel empowered to take action rather than just berating them into compliance.

2. “Uuuushy-guuushy, touchy-feely, go-nowhere” coaching

This kind of coaching is on the total polar opposite end of the spectrum from the “yelling at your client” session. It usually involves asking the client where they want to go and then wandering around with the client until they stumble upon some sort of insight.

This style usually leaves the client with a vague feeling of something changing or happening but without really being able to put a finger on it. If you were to ask a client what happened in a session they would struggle to explain it, but not in a “my being shifted so much I don’t have words” sort of a way, but rather more of an “I don’t really know if we did anything but I’m afraid to admit it” sort of way.

Still, coaches—especially coaches on the more spiritual or woo woo end of the spectrum—love this kind of coaching because it feels in alignment with flow, the universe, or some goddess energy they made up last week. It’s also great because clients who believe what the coach believes feel really good in these sessions. Partially because they don’t really have to change, nothing is really on the line, and it’s more about them “feeling” like they’re doing something, or the “experience” of transformation more than anything else.

Where it starts:

Again this type of coaching starts in the Drop—or should I say, the LACK of a Drop. Sessions with this coach never seem to go anywhere… but you probably don’t notice because they never seem to start anywhere either. They are guided by the client’s feeling in the moment and while they can feel good—sort of like gentle back rub—this lack of a Drop causes pretty major problems down the road.

The problem with it:

The biggest problem with this sort of coaching is that it’s both ineffective and it tends to empower people to make excuses or justify their own untransformed ways of being. It’s also problematic because it’s really similar to REALLY POWERFUL DEEP COACHING which can also go with the flow, have lots of spaciousness, and be guided by a spiritual coach. It’s sort of like a knock-off pair of sunglasses. The lenses scratch easily, the logo rubs off super fast, and the hinges break, but it’s okay, because it looks like an expensive pair of sunglasses at first.

Even worse, this kind of coaching hides it’s shiftiness in a layer of affect and spiritual aphorism, equivocation, and other subtly delusive thinking, which makes it even harder to figure out. Any objection to it not working is often met with suggestions about being out of alignment, with the universe’s negative vibrations, or something about chi or chakras—which sounds true but really just ends of confusing and obfuscating the vague meandering that the coach claims is a process.

If you think you might be doing this kind of coaching, please read EVERYTHING we wrote about the Coaching Canvas and really focus by starting your sessions by finding out what your clients want. Just adding a lil bit o’ structure to your sessions can make a BIG difference.

3. “Telling wrapped in silence” coaching

This kind of coaching share similarities with both the previous types. It has both the uuushy-goooooshy feeling of go-nowhere coaching and a subtle form of bossy-ness that exists in “yelling at your client” coaching.

Of course, these are tempered by the other, which makes it even harder to notice if this is happening.

This coaching is often denoted by long stretches of silence, which add an air of significance to the sessions but not much else. The questions are sparse and simple, which hides the fact that they’ve been regurgitated hundreds of times, and are designed to have a client dance on a string for the coach. When used by newer coaches this kind of coaching has the quality of an awkward puppeteer playing with someone else’s dolls, but it’s no less insidious.

What really sets this coaching apart, though, is that these questions are always followed by subtle suggestions or observations that are crafted in a way to seem really insightful, but are actually just advice in a clever format. Each suggestion is followed by silence and a “What if?” feeling that gives a sense of awe to the whole vibe, but the coaching itself is only crafted to look original, even though it isn’t.

The stories the coach tells sound good, because they’ve been told dozens of times. The feeling of the session is magical, not because of the magic but because of the careful persona the coach has learned to craft or is pretending to craft in the moment. If the coach is experienced, it’s only after working with this coach for six months to a year that you begin to see the game, perhaps less if the coach is newer to this art form. But the effect is the same: you start to wonder if you’re going to get any coaching this time or simply the performance of coaching they trot out every time they do a session.

When it starts:

Again this starts in the Drop. Instead of the coach being with the client and finding out what they would like, the coach carefully nudges the client down some predetermined path only the coach can see, if they are even aware of it. And because of this, the session doesn’t Drop into the client’s possibility, but merely the coach’s script of various coaching options.

The problem with it:

The biggest problem with this kind of coaching is that it LOOKS REALLY GOOD!! In fact, this kind of coaching is optimized for observation and performance. It’s not messy in any way, it’s not even wild. Instead, it’s clean and polished, and the more experienced the coach, the more polished it is. And so it’s really hard to notice that the session isn’t actually that powerful.

Probably the worst part of this style of coaching is that it debilitates both the coach and client, because as the coach gets better at it, the sessions start to feel easier and more amazing, and the clients are more willing to buy into how amazing they are, even though the sessions have started to rot from the inside out.

This can be one of the hardest shitty ways of coaching to root out; it’s something experienced coaches have to be on the lookout for. If you’re a newer coach this kind of coaching usually starts out as a form of imitation, which is of course a great way to try on different styles of coaching. But eventually it becomes so much of an homage to the coach you’re copying that any sense of you or even the client in the session is entirely lost. If you think you’re doing this kind of coaching, add a bit more of yourself to the session or find a way to break your coaching rules and have a session that is 10x more messy than any session you’ve had in a while.

Not All Coaching Is Shitty

I’m realizing now as I finish this post that I could probably list out at least a DOZEN or more shitty kinds of coaching that you need to watch out for, but in truth A LOT of the coaching I’ve seen that subtly sucks falls into one of these categories in a big or small way. But don’t worry, almost every coach I know who’s any good has done a few sessions like the ones I described above. If you pay attention, get feedback, and keep working on your coaching you’ll notice that you’re doing one of these pretty quickly and be able to stop.

Really, the only way coaches get stuck in these types of coaching is when they don’t get feedback from their peers, stop studying their art, and double down on their way being the “right way” to coach.

When we lose our humility as coaches, we lose our mastery, so long as you can stay curious, stay humble, and keep learning, you’ll be able to ferret out these insidious kinds of shitty coaching. But of course that’s what practice, a community of mastery, and dedication to the sacred craft of coaching is all about.




The Next Coaching Dojo and Sales Dojo start on March 8th, 2019.

Priority Deadline: January 7th

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Dangerous Coaches Wanted

Coaching that is 10x better doesn’t happen because you’re paying ten times the attention, or because you’re charging ten times as much, or because you’ve coached ten times the number of clients.

A mediocre coach can’t become masterful simply by taking one quality of mastery and doing it ten times as often. But we often think like this:

  • A coach will notice how much silence there is in a Rich Litvin YouTube video and vow to be silent for half a session.
  • A coach will be enthralled by Tony Robbins’s hardcore pushing of his audience members and begin to yell at their clients for NOT DOING THEIR WORK.
  • A coach will be amazed by the simplicity of the Ten Step Executive Development system in a book and begin running all of their clients through it, like pushing meat through a transformation grinder.

And at first something happens, because it’s different, and the effect is different. But eventually your clients adjust to the change. They fill silence with nonsense, they comply to your yelling even though it disempowers them or they fire you very politely, or they go through your process and get something out of it. But nothing really changes for them.

The reason there are so few truly exponential coaches isn’t because of a lack of talent or spiritual depth, it’s that the coaching industry echo chamber and our own subtle arrogance convince us we can become masterful by doubling down on our coaching “religion” or preferred technique or system.

Creating a 10x Drop is possible, but it requires a commitment to mastery first, which also means you have to let go of the certainty, easy platitudes, and simplistic coaching catch-alls that you may have convinced yourself is the safer path to walk as a coach.


Dangerous Coaches Wanted:

For hazardous journey, certainty abandoned,

the rules of coaching dismantled, long hours of soul searching,

seemingly unanswerable questions, constant danger to your being,

survival of your current self doubtful

depth, transformation, and possibility in case of success.

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A Simple Exercise that Makes You a Better Coach (by making you better at the Drop)

The Drop can seem a bit mysterious sometimes—and I have to admit that from time to time I’m at a loss for words to explain it, teach about it, and help you understand it.

In some ways the Drop is the whole pivot point of a coaching conversation. And yet, even in saying this, I make is sound singular—when it truth it’s often not.

In some ways the Drop is incredibly magical. And while it feels magical, there are not spells or incantations for you to chant. And yet, it also has its own sacred form of mechanics.

In some ways the Drop is so complex, it can feel like staring into a seven-dimensional ice cave through the eyes of a mantis shrimp… And yet, it’s also incredibly simple.

And it’s this last AND YET that I want to offer to you as a practice today.

Here is a simple exercise that will make you a better coach, by helping you be better at the Drop:


Imagine your client arrives to your session and just as they sit down they are struck on their head by a magical rock.

As soon as the rock hits them, they become confused. They don’t remember they were hit by a rock. They deny this ever happened, and in their confusion they don’t realize they are confused at all. In fact, they don’t have any memory of what it means to not be confused.

They think their confusion is clarity. And so any attempt to convince them that they are confused will be met with its own form of confusion.

Your job is to coach them so that they come to see that they are confused.

Okay, so right about now you’re probably confused, mad at me, or a little bit of both. But I’d like to remind you that the exercise is simple, but not easy. In fact, this may be the most difficult session you’ve ever coached.

But the question at the core of it is incredibly simple:
How do you coach someone who is confused?

Or if you want to make it more complicated:
How do you coach someone who is confused and in their confusion has confused clarity for confusion?

And yet both of these questions—even the simple one—capture the essence of the Drop.

One thing I’ve learned as a coach is that our clients are ALL master manipulators. And I don’t say this to be mean. After all, I’m a client, so I’m a master manipulator as well.

The reason I can say this without judgment is that even though your clients are all master manipulators, they have no idea that they’re doing it. They are 100% convinced they are telling the truth—about their lives, themselves, the world. ALL OF IT.

But they aren’t. They are simply telling themselves just enough of the truth so that they don’t really have to change anything.

There are lots of words and phrases that point to this:

  • Survival mechanism
  • Denial
  • Unconscious unconsciousness
  • Things that you don’t know, you don’t know

The list goes on and on.

And yet this is what your clients show up with.

Your clients show up confused.

Some have small confusions:
I think I have to say yes to this dinner party I don’t want to go to.

Some have medium confusions:
I think I have to get this person to like me, in order to be okay with myself.

Some have BIG confusions:
I think I am powerless in my life and to my circumstances.

But no matter what, they show up confused.

And your job is to coach them.

BUT WAIT . . .

That’s not ALL . . .

You are ALSO confused. In your own way. About what’s possible for you and in many ways what’s possible for your client.


Well, I have good news. The good news is, if you are a coach, you probably know you’re confused. Though you may forget from time to time.

Part of a coach’s job—maybe the most important one—is to know that you are confused, to remember that you are confused, AND even more importantly to remember that your client is confused.

Your client is confused and they are confused about their confusion. And in the DROP you help them get they that are confused, or you create the possibility of them being open to being confused.

Simple, right?

Well, the exercise itself is actually simple even if you now feel incredibly confused.

If you are, stand up and SHAKE IT OFF! SHAKE OFF THAT CONFUSION!!!

Okay, are you back?


Now before the next time you coach, write on a Post-it note:

Then the next time you coach, after your Open, short or long:
Simply look at your piece of paper as you create the Drop.

At first this might seem hard, but notice how your client will try to convince you they aren’t confused. They will try to convince you that what they want is what they want, that they understand their issue perfectly, that the session should 100% be about coming up with a better email sorting system.

But just remember: THEY ARE CONFUSED.

Your job is to coach them so that they come to see that they are confused.

NOT to tell them they’re confused.
NOT to help them in their confusion.
NOT to agree with them knowing they’re confused for the sake of expediency.

NO, your job is to coach them so that they come to see that they are confused.

And as soon as you begin to get the sense that they are beginning to see they are confused or that they become open to the idea or truth of their confusion…

That right there is you creating the DROP, coach them RIGHT THERE!!

Right at the crack in their confused confusion.

Simple and yet sacred. Deep. Powerful. A lifetime’s worth of practice right there.

Thank you for practicing, from the bottom of my heart.


The Next Coaching Dojo and Sales Dojo: Starts on March 8th, 2019.

First Priority Deadline: January 7th

Apply Now: –

What are the best questions to OPEN YOUR CLIENT UP and find out what they want?

(AKA the Dopest Drop Questions EVERRRRRRR…)


Coaches love questions. We collect them. Admire them. DROOOOOOL OVER THEM.

So even though part of me knows that coaching isn’t really about the questions alone—sort of in the same way chess isn’t about the pieces, or music about individual notes or phrases—I can’t help but want to give you what I too would want. So here you go. These are my three favorite, tasty, delicious, juicy, organic, farm-to-table, artisan Drop questions you can use to be SUPER DOPE AF about your Drop.

Question 1: What would you like?

I know, I know, I used this question in the Open series earlier. I’m sorry for giving you leftovers to start off with, but this question is a really good one.

When to use it:

Always forever and often. This is perhaps one of the best universal coaching question I have ever encountered. You can use this for opens, drop, re-drops, shifts, and even closes. In my mind this question is like salt or sriracha is goes with EEEEEEERRRRRverything.

How it works:

The beauty of the question is that it immediately invites the client to look at where they want to be. Most of us know what we don’t want (= the past) unless the past was really great and we want to get back to it. Of course even with clients like this, they still don’t want the past, because they want whatever they had in the past without having to experience losing it.

So yep, clients can tell you ALL DAY what they don’t want. But this question directs them to say, “Hey, what DO you want?” And it does it while not adding something that can be really problematic, which is SIGNIFICANCE. While I love the possibility of Rich Litvin’s “What would make this conversation extraordinary?”, it runs the risk of adding significance, and in doing so it can also make a conversation incredibly heavy and bring in all the pre-preconceived obstacles we have to getting what we want.

That’s why this question is SO DOPE!! Because it asks the client to look at the future like a menu. After all, when we order food at a restaurant we rarely ask ourselves, “WHAT WOULD MAKE THIS MEAL EXTRAORDINARY?”! Now I’m not saying this would be a bad question, but I am saying that it may make us feel a sense of PRESSURE—pushing down on me, pushing down on you—as you order your food.

And it’s why “What would you like?”—in its simplicity, lightness, and subtlety—can be so powerful.

What to watch out for:

Mostly you have to watch out for the client telling you what they don’t want, or finding a way to say A BUNCH of words without answering this question at all. So mostly you just need to make sure they answer the question in a way where you get what they want and they get what they want.

The other risk is they say, “Well, I don’t know.” And this can happen, but what I find is “I don’t know” is very often a subtle way of saying, “I don’t know how to get what I want so that means I don’t know what I want.” We mostly know what we want. It may just be a feeling. Or an amount of money. Or some kind of respect. Or status.

Seth Godin describes what most people want quite beautifully in his book This Is Marketing. “You’d like to be respected, successful, independent, appropriately busy, and maybe a little famous. You’d like to do work you’re proud of and do it for people you care about.”

So don’t be fooled by “I don’t know.”

If you want to go deeper:

Read the next question.

Question 2: And what would having that do for you?

At this point I’m basically just stealing from Jeff Riddle and Carl Bucheit’s bag of coaching genius, but both of these questions are really truly beautiful questions.

When to use it:

As soon as someone tells you what they want or they describe something they want to create in a session and you think there’s probably something behind that—something they actually want. And what you’re hearing about is their strategy to create it, rather than what they actually want.

How it works:

This question is built on a simple premise. People don’t go after what they want, they go after the thing they think will create what they want. When you ask people how much money they want to make they might be able to say a certain figure. For a LOT of coaches this is six or seven figures.

But that’s really just a number. On its own it’s meaningless. For example, in the first year of my coaching business making $15k in a single month sounded AMAZING!! Now, on average, our business needs more money than that just to function. Which means that if I make $15k that’s a BAD month for us.

So all numbers are just a matter of perspective. The reason coaches say they want to make six figures is they think they will have “made it” when they get there and they can say they are “successful” coaches. They imagine it will gives them a status they want and a feeling of “security.” But I can assure you, being a six-figure coach as a status doesn’t mean that much to me anymore and there was no security package that arrived along with it.

This is true for almost everything your clients say that they want. This question cuts underneath that and asks about that next-level thing.

In the end, if you follow this down far enough you’ll get to something like love, acceptance, or freedom of expression. This is the core of what they want. And it’s why this question is so powerful.

What to watch out for:

This can be a hard question for people to answer and often they don’t totally know. In fact you can create a DROP right here. Finding out what’s behind something someone has wanted for a long time can be a powerful session. AND if you are wanting to do something with more than that, it’s important you slow down and figure out the thing behind the thing, because otherwise you can solve a problem without resolving the existential kink in their hose of being.

If you want to go deeper:

Read the next question.

Question 3: What might you lose that you value, when you can have what you want?

You know, it’s funny… when I started writing this post I didn’t intend this to be a breakdown of Carl Bucheit’s power questions that I got from Jeff Riddle. But it’s sort of just what ended up happening. Which is why I want to pause and say if you like these questions, GO STUDY TRANSFORMATIONAL NLP. They have an incredible program at NLP Marin and it’ll make a HUGE impact on you as a coach if you do. This model HIGHLY influences who I am as a coach and it’s POWERFUL. Okay—on with the show.

When to use it:

Use this anytime it feels like something in the way that’s hidden. If someone is blocked or in impossibility around creating what they want this is a great way to discover what that thing is.

How it works:

Early on in my career as a coach I learned about this thing called “competing commitments” from Jason Goldberg. The concept exists in some form in a BUNCH of different transformational models.

The basic idea is that there is always a payoff for the things we do that keep us stuck. Procrastination, avoidance, inactivity, gives us some GOOOOOOOD STUFF. If it didn’t, we would stop doing it. People who like getting spanked for sexual pleasure will ask to get spanked. If you don’t relate to spanking this way then you probably won’t ask to get spanked a lot.

This question helps reveal what’s at stake for your client’s desires. Because something is always at stake. It’s often not something rational, reasonable, or even present in the current moment. In fact, it’s almost always something from the past. Something they don’t want that they are trying to avoid.

If you say you want a lot of money but are afraid you will become a rich greedy jerk, you are afraid you might lose your authenticity or integrity when you can have the money you want.

If you say you want to go on a nice vacation, but keep not booking it, because you know you’ll feel guilty and indulgent, you are worried you might lose your status as a responsible, thrifty person when you can have the vacation you want.

This question, when used well, can reveal these hidden obstacles with ease.

What to watch out for:

The main thing to watch out for is confusion. People will often deny they will lose anything that they value when they can have what they want. They think it will be ALLLLLLLLL upside. But if this were true they would probably already have it.

The fact that they don’t reveals that something is missing, either in their being or their mastery. But a lot of people have a hard time seeing this. Which makes sense because we’re dealing in the hidden commitments, desires, and belonging.

Again, this question by ITSELF can be a Drop. ALL THREE of these questions can create a Drop in different ways. You can spend a whole session looking for and at what’s at stake for a client in getting what they want. You can actually spend AN ENTIRE COACHING RELATIONSHIP doing this.

And have it be really powerful.

If you want to go deeper:

Learn a model of transformation that helps you examine these forces with ease. There are a bunch of them out there. Transformational NLP looks at these forces in the terms of the brain, the unconscious, family systems, and quantum physics. Landmark uses a whole different set of tools to do this work through distinctions like stories, enrollment, possibility, and authenticity. Zen Buddhism uses a whole ’nother set of tools and practices.

In some ways all the models I’ve seen address this on some level, but if you have studied, practiced, and learned any of these models deeply GO DO IT. Take the Forum, study at NLP Marin, just pick one and learn it.

In the Dojo we teach elements of all of these as foundational frameworks. AND it can be really helpful to know one really well.

Closing Thoughts

Knowing a question and mastering it are two different things. I’m still working to master the question:

“What would you like?”

I still work to understand when to use it, when I can take and answer and really be with it and use it to create a session.

This is true of all of these questions, so DON’T STOP NOW!! When it comes to mastering these three questions, try them out, study how they work, reflect on where the gap is.

Coaching is a sacred art and questions are powerful incantations for possibility. Don’t forget that. Don’t be afraid to use them, but also don’t step out of wonder and curiosity with them either. Dead questions are like dead coaches—not much use to anyone at all.


Analyze the best Drops and make your own list of favorite Dope Drop Questions with the Coaching Canvas tool. Get your copy here.

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.