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  • Jason R. Waller

How to Craft Powerful Questions that Uncover True Meaning

Updated: Mar 6, 2020



Did you know that there’s one tool I use in every single coaching session? It’s the most important tool that I have, and one of the most important things I teach leaders. It’s the ability to ask truly powerful questions.


Why are powerful questions so important? It’s actually pretty simple — as leaders, we can’t change what we don’t understand. And as a coach, I can’t help people change what they don’t see.


Powerful questions help to:


  • Challenge others to dig deeper

  • Invite them to be brave and vulnerable

  • Show others that we are interested an invested

  • Take us into a more active state of listening

  • Give us more context and information on what really matters


And a ton of other reasons. So how hard is it to ask powerful questions? It’s actually not hard at all. We just need a little bit of practice and a few guiding principles.


1. Powerful questions are open

“We cannot teach people anything; we can only help them discover it within themselves.” –Galileo Galilei

A closed question is one that can be answered with a word. Usually “yes” or “no.” “Are you going to stay late?” and “Do you like this color?” are all closed questions. They can be answered simply and then they are closed. They don’t ask much engagement of the other person.


I actually first came across closed questions when I was working in a sales job in my youth. Closed questions can actually be quite useful in sales! “Do you want to start your membership on Wednesday or Tuesday?” “Do you like the red one or the orange one better?” These questions almost demand a response, and they can move people to action! But do they actually lead to deep learning? No.


Open questions, on the other hand, are just that. The answer can be anything. It doesn’t just invite response, but consideration and engagement. “Why are you going to stay late?” and “What about this color do you like?” are all open questions. They start with who, what, when, where, why, or how.


The real value of an open question is that it creates both a reflection and a dialog. By asking someone an open question, you ask them to step back and really consider. You show them your interest and invite them to engage. For leaders, all the above is critical.


The next time you have a conversation with someone, especially someone you’re working with, check your questions. Are you asking closed questions and keeping the other person disengaged? Or are you asking open questions that really get to the heart of an issue and foster collaboration?


Important note: what > why or how


Not all are open questions are created equal. At the lowest hierarchy are questions starting with who, when, and where. In fact, these might be closed questions if they don’t invite depth. Asking why or how is in the middle hierarchy. They encourage reflection, but there is still an even better way.


The top tier of powerful, open questions is the “what” question. It’s both open and less confrontational than why or how. This is a matter of subjectivity, sure, and a lot of cultural weight comes into play here. But take note of how these questions feel to you:


Why are you going to stay late?” versus “What is making you stay late?


How are you going to accomplish your goal?” versus “What are you planning to do to accomplish your goal?


It’s a simple shift, but the second set of questions will feel less judgmental to most people. “Why” can make people feel like they’ve done something wrong. “How” can make people scramble to explain and justify themselves.


Try rephrasing your questions to start with “what” when you can. It takes practice, but I promise it’s worth it.


2. Powerful questions are concise

“Speak only if it improves upon the silence.” –Mahatma Gandhi

Another good quote by Mark Twain: “I didn’t have time to write a short letter, so I wrote a long one instead.” If you want a question to be powerful, keep it short.


The most powerful questions are less than ten words long. They are easy to understand, and ask the receiver to consider only one thing. Only one thing. Don’t get caught in the trap of multi-part questions. Focus on the topic at hand and ask the question you need to ask. There will be time for follow up later, if it’s even needed.


All too often, our tendency is to make questions longer than they really need to be. Ask yourself why you do it. Are you unsure of what you’re asking, so you take extra effort to to really clarify what you’re saying? Are you worried that it will be taken the wrong way, so you take extra effort to soften the message?


Just pause, reflect on what you need to ask, ask it, and then pause again.


Important note: get comfortable with silence


On the note of pausing, try to do it more. But especially after asking a really powerful question. If you’ve just asked a question that has real weight to it, let that weight sit in the room. Silence is uncomfortable, but it’s necessary.


Silence is an opportunity for the other person to really reflect on what you asked. It’s a way to give them space to think and create a meaningful answer. Silence is also an opportunity for you to listen. Not just to their reply. Listen to their body language, their cues. Look for the impact the question is having on them.


3. Powerful questions are meaningful

“Listen to the whispers and you won’t have to hear the screams” –Cherokee proverb

It might go without saying, but powerful questions have real impact in them. They challenge people to dig deep. “What is the next step?” looks like a powerful question. It’s short and it starts with “what.” But it might not be meaningful.


What is holding you back?” is a powerful question. “What would it mean to you to accomplish your goal?” is a powerful question. Ask questions that drive deeper reflection.


This can be vague, but a simple rule to help is: don’t focus on the problem, focus on the person. Problem solving has its time and place, for sure. But if you’re trying to uncover deeper meaning and work to take someone to a new perspective, focus on their experience. What do they want? What’s holding them back? What are they afraid of?


Important note: follow the thread


As a coach, I try to release my own agenda as much as possible. I try (sometimes unsuccessfully) to let the client lead the discussion. As a leader, this might not always be an option. But you’d be surprised how often it is, and how powerful it can be to work toward the same goal when the other person is leading it.


Practice following the thread of what matters to the other person. What did you notice really mattered to them? Where do they want to go? Even if it’s not 100% aligned with where you want to go, at least you’ll understand them and their situation better. And in making important decisions of offering advice, it’s always better to have more context.


Closing thoughts


I recently had an entrepreneur reach out to me on Twitter. He had read my article How Founders Can Build Extraordinary Leadership Through Vulnerability and had a question about his co-founder. He was concerned because the co-founder didn’t seem to be invested in the product launch, which was only a month away.


Without any background, I could only give one suggestion. You guessed it — powerful questions. I encouraged him to figure out what was at the core of the issue (assuming it actually was an issue to the other person). The situation illustrates an important point: context doesn’t really matter. The questions matter.


Powerful questions come from a place of curiosity, from a beginner’s mindset. It’s an approach that I use in every coaching session to uncover what really matters to my clients. To challenge them. And leaders can use it in the same way.


Try making your questions a bit more powerful. Practice making them open, short, and meaningful. Share with others how they can be more powerful in their questions. And, as always, let me know how it goes.


Originally published on The Ascent