Box of Crayons Blog


Coaching Questions: Ask What, Not Why

We see it in television shows, movies and even comics. One character had the answer to the dilemma all along, and when questioned as to why they didn’t say anything, their response is: “You didn’t ask.”

“You mean you could have deactivated the bomb anytime? Why didn’t you tell us?”

“You never asked.”

You can’t get answers if you don’t ask questions. And, more importantly, you can’t get the right answers if you don’t ask the right questions.

Mastering the art of asking a powerful question is the key to freeing up your time and empowering your team. The more questions you ask, the less advice you give, and the more your employees learn and develop.


Knowing What to Ask

Just as important as how to ask a question is what exactly you ask.

In her book Living Your Best Life, Laura Berman Fortgang talks about the common question of “Why?” — and reminds us that we start asking this at a young age. When I think about this, I immediately picture a five-year-old asking, “Why is the sky blue? . . . Why? . . . But why?”

While that “why” really helps us as children, it loses its strength in certain areas of our lives as we grow older. It doesn’t always bring forth the wisdom we’re looking for when we ask a question. Laura points out that asking “Why?” can definitely be the key to great discovery, but it’s not an effective tool when it comes to making changes.

She suggests asking deeper and more useful questions. She gives this example in her book: “If I asked you, ‘Why are you reading this book?,’ you might tell me a story about some things you are wondering about. Maybe you’d go on to provide a few details about what brought you to this moment of information seeking. Your responses would probably have something to do with your past.” But if you were instead asked, “What outcome do you want to reach by reading this book?,” your answers would become future-oriented, she says.

It seems to me that asking “What?” instead of “Why?” might just be one of the ways to ask a good question. Replace your usual “why” questions with updated “what” questions and you’ll be surprised at how forward-thinking the conversation becomes.


Instead of: Why are you here? Ask: What’s on your mind?

When someone schedules a meeting with you or wants to have a conversation, you probably think, “Why is this person here?” Because at the end of the day, you want to know what exactly they are doing in your office. But rather than asking them why, ask them what. The Kickstart Question — “What’s on your mind?” — transforms your why into an open-ended question that gets to what matters most. It cuts through the banal chitchat to uncover what’s going on. (And then you can follow it up with the best coaching question in the world: “And what else?”)


Instead of: Why are you struggling with this? Ask: What’s the real challenge here for you?

The Focus Question — “What’s the real challenge here for you?” — is meant to get to the heart of the matter. It still addresses the “why” that you want to know, but it brings clarity to the issue at hand and makes it personal by asking the other person to explain what the challenge is for them specifically.


Instead of: Why are you coming to me? Ask: What do you want?

“What do you want?” is the Foundation Question. With it, you’re asking the other person to really think about what they want. This is different from asking why they are coming to you, which will often only elicit a response of “Uh, because, uh, you’re the boss and . . .” That reply doesn’t help anyone. By forcing them to think about what they want, you’ll also find out what, if anything, you can do to help.

What can I do?” and also what I call the Lazy Question — “How can I help?” — are good questions to ask because they keep you curious. “What do you want?” will narrow in on what exactly the person is hoping to get out of the conversation, but the Lazy Question forces them to make a clear request of you. It answers the “why” that you needed but also draws out more.


Instead of: Why can’t you do this? Ask: If you’re saying yes to this, what are you saying no to?

As a busy manager, you probably know what it’s like to be overwhelmed and overcommitted. Strategy (a highly abused word, in my opinion) is all about knowing when to say no to an idea in order to really define another yes. Asking the Strategic Question — “If you’re saying yes to this, what are you saying no to?” — forces the other person to think and prioritize. It brings them closer to their Great Work and helps them decide what they need to let go of. It also asks it in a safe way. You can see how a question like “Why can’t you do this?” might cause a fight-or-flight response and make the other person feel like they should keep piling on the work.

We learn from one another by asking questions, and we inspire our teams by doing so too. The Learning Question — “What was most useful for you?” – is a way to finish a conversation with meaning on both sides. It creates an opportunity of learning, as it encourages the other person to reflect on the conversation, which is what leads to insight and learning.

Knowing how to ask a question well is what helps you stay lazy. A good question keeps you curious and helps you give less advice and do less work, while having more impact.


2 Responses to Coaching Questions: Ask What, Not Why

  • Don Smith

    Michael, thanks for this helpful blog. I’ve long held that the most important and most interesting question is “what should you/we/I do about this?”

  • Barry Wilding-Webb

    Michael, Thanks for the reminder of the power of the ‘what?’ question. ‘Why’ is a great question but can sometimes be interpreted as somewhat challenging and occasionally judgemental if you ask it with a rising tone, as if you’re saying: “There is a better way of doing this…” Clients can quickly become defensive which is the opposite effect you intended. Barry

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