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

By Toku

(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.

Great coaches enroll amazing clients. Download my free masterclass on how to enroll clients with skill and honor.

Apply Now

To start the application process, fill in your full name and email and you’ll be taken to the application page.

Free Masterclass

Great coaches enroll amazing clients.

Download my free masterclass on how to enroll clients with skill and honor.