The 5 Whys Blueprint

By Toku

Every coach with a desire to do deep work, longs to help create a powerful shift in each and every conversation. And while the depth that you go with a client is dependent on many factors, the place you start from is perhaps the most important.

Imagine if you had to have a bullet removed from your shoulder. Would you want the doctor to open up your chest and go up to search for the bullet? Or would you prefer they find the spot the bullet entered and dig into the hole it made to find it and pull it out?

If this answer seems obvious it shouldn’t be. Many coaches out of ignorance, enthusiasm, or both start performing open chest surgery before truly understanding where to begin their work. As Sensei and members of various different coaching communities, we’ve seen coaches rooting around for topics or trying to ‘get somewhere’ with clients without knowing where exactly they need to begin.

Here’s a technique we love using with clients and with ourselves called “The 5 Whys”. This simple, but powerful technique, is highly effective at helping you take yourself and your clients deeper. While we don’t recommend you use this with every client in every situation it can be handy for helping you practice the art of finding a powerful place to begin a deep conversation.

We want to share a little bit about how we use this with clients and how you can use it in your own practice.

Before The First Why

Before you get to the first why there’s some important things you need to do, to lay the groundwork for this exercise. While we could write a whole post just about this groundwork, we wanted to mention it so that it wouldn’t be lost.

Before you ask your first why, you need to make sure you’ve created the three C’s:

  1. A Safe CONTAINER – the key elements of a safe container are:
    1. Rapport with your client
    2. A set of powerful agreements
    3. An outline of what will happen before, during, and after your conversation
  2. A Powerful CONTEXT – the key elements of a powerful context are:
    1. Expansive possibility
    2. An intention for the call
    3. Energetic resonance
  3. Incredible CURIOSITY – the key elements of incredible curiosity are:
    1. Trust for your client and your own deep intuition
    2. A willingness to step into the unknown
    3. Surrender of your bias, judgements, and any fixed beliefs of the way it “must” or “should” be.

There are many ways to create the elements above, how you do these is not as important as your willingness to do them. If you take the time to lay the groundwork before the first why everything else that follows will be more powerful.

While this can seem like an overwhelming list, in truth I’ve seen coaches like Rich Litvin, Toku, and many others do all of these in a matter of a few mins. Especially if you’ve already done some work with the client before this call to establish trust, rapport, and a sense of your ability to lead them powerfully.

The First Why

Once you’ve laid the groundwork for a powerful session, you can begin with your first why.

The Set Up –

First, you have to set this up by asking a question. While there are many questions you can use, here are some of our favorites:

  • What would make this a powerful conversation?
  • What would make this conversation extraordinary?
  • What could we create together today that would make this conversation life-changing?
  • What would make you gleefully happy?
  • What’s something you want but are afraid is impossible?
  • Where’s your attention being drawn?
  • What’s coming up for you the most in your life?
  • Where are you avoiding?

The point of each of these questions is to find out where the client is at and what they want. What they long for and deeply desire. Remember you’re not looking for the ultimate answer, just a place to start.

Knowing when you’re ready to start –

What you’re looking for in a coaching context is: “Does the client really want this or at least think they do?” If the answer they give doesn’t land for you, or doesn’t seem totally honest, you may want to ask them again in a different way what is they really want before you get started.

While the 5 whys work with almost any desire, they will work even more effectively if the client expresses a desire that is close to home for them.

Asking –

This part is easy. Just ask the client why? Or some version of it. Some other versions of why are:

  • Why do you want that?
  • What would that give you?
  • What would that create for you?
  • What would that do for you?
  • What might that mean about you?
  • What makes that important for you?
  • Who would you be if you had that?

These question variations are especially helpful when the client responds with “I don’t know?” Of course if they continue to say I don’t know, you can always do what one member of the Dojo once did, you can say “well let’s google it!” This is surprisingly effective at breaking tension and helping the client relax into the situation. (Thanks to Mark Pettigrew for that one!)

Listening –

Now you listen, listen deeply, listen for what they want underneath what they first desired. Notice if they are trying to justify wanting it which is different than revealing what’s underneath their desire. Slow down and listen for the lost or unspoken desire. And make sure to notice and pay attention to common patterns around desire.

You may know from experience as a coach or as a human that our desire to make ‘lots of money’ is often a desire for safety, freedom, recognition, or love. So listen deeply and reflect.

Keep reflecting until something lands with them. When it does, slow down, pause, let that insight sink in. Your client might be excited about this little insight. Slow them down as well.

Once it has sunk in, you’re ready to move on.

The 2nd, 3rd, and 4th Whys

The 2nd why digs deeper but the same principles apply. Ask powerfully and listen deeply. Reflect their answer and let the insight sink in. Feel into if you’re going deeper or in circles. Notice if you start moving sideways. One sideways move is fine, but if they keep moving sideways they may be avoiding something that is more true. Some desires they may feel ashamed about. So don’t give up and trust your instincts until you feel it in your gut.

If they go sideways maybe ask them that same level of why again. Ask them: What’s underneath that? What would that really give you? Don’t give up, they can go deeper, if you slow down, if your heart is open, keep going… down and down and down.

The 5th Why

The 5th why is a bit of a misnomer. It might take 5 or not. 5 is a good number because it requires patience and curiosity. You can rush through 3 whys but 5 makes you slow down. So, no, there’s nothing special about 5 and yet 5 is powerful. It may take 8 whys to get to the 5th why. Or it may take 1. It’s not about the number it’s about the depth. At first do at least 5 whys, but over time you might realize you don’t actually need that many.

How do you know if you’re at the 5th why?

You know you’re at the 5th why when you land on a foundation belief. A belief usually related to belonging or a core wound. Here are some examples of 5th why beliefs

  • I want to be loved
  • I want to belong
  • I want to feel safe
  • I want to feel worthy


Here’s a quick summary of general 5 why steps:

  1. WHY are you here?
  2. WHY are you really here?
  3. WHY is that so important to you / why do you care?
  4. WHY are you holding yourself back / afraid / resistant / protective?
  5. WHY are attached to this pattern / belief / story / behavior?

Beyond The Why

Once you get down here you’re there. You may not want to go further. If you do you might discover a story from their childhood where this foundational belief begins. Or you might have found the core of an old wound they’ve been afraid to heal.

Remember the 5 whys are not a coaching session. They are a way to get started. Once you get down here, you can make an impact, not just by asking why, but by getting to a deep belief or wound and then reframing or challenging the fixed thought behind it.

This is the art of the 5 whys.

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