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How to become a better questionologist (one who asks better questions)

I wanna know

It’s not a coincidence that the smartest people I know, the most promising students I've worked with, and the most curious of kiddos ask me the best questions.

If you stop and think about it, so much is dependent on asking good questions: relationships, science, innovation, etc. Thoughtful inquiry inherently affects progress in all aspects of our lives.

So, why don't we ask questions more often? Why don't we focus on getting better at it?

I became interested in the topic of better inquiries based on interactions with a particular patient. I was struck by his superb questions. They weren't typical. They caused me to pause and reflect before answering. I often thought about the topic from a new or different viewpoint. I started to realize I was giving better answers, better information and learning in the process. So, naturally I wondered....




You can’t have an answer until you have a question


The best questions in my mind are the ones asked for curiosity-sake alone, not with a desire for a certain answer. There is an art to questioning as you seek information. Fundamental to science is asking questions. So better questioning blends art and science.

The best inquiries are those that push us both in our work and in our personal life to make positive changes. These "better" questions make us think, hopefully in a manner that we haven't before.

Warren Berger, in his A More Beautiful Question, describes a better question as being:

· ambitious

· actionable

· creating a shift in our norm of thinking

· creating an impetus for change

Good questions move past requesting a yes/no answer. They request details. They make you ponder. Being asked and asking better questions has changed my perception and thought process in many aspects of my life.


To answer this question, I started by reading and listening. Reading is my go-to for learning these days but I also listened to a couple of great podcasts and TED talks. See my list at the end.

Here is how you do it:

First off, are there prerequisites to being a good questionologist? YES, you need to be open-minded:

  • "Open minded people genuinely believe they could be wrong. The questions they ask are genuine. " -Ray Dalio

Got an open mind? Proceed.

Focus on open-ended questions most of the time, not ones that can be answered in one word. It is pretty obvious that you will get more information from the questions in italics.


"What’s the best part of your day?" vs. "Did you have a good day?"

"What are your thoughts on a Paleo diet?" vs. "Do you agree with a Paleo diet?"

Three of my favorite open-ended questions are:

"What if…..?" Example: What if we all asked better questions?

"Tell me more" and "Explain that to me" Some questions work best when they don’t end in a question mark.

Think of Questioning as an activity, maybe even PLAY:

The critical part of learning anything is the active part. You can sit back and read all day but if you don't become an active questioner it’s all for not. So I started to implement and test out what I've read. I found with almost everything: different strokes for different folks.

Socratic questioning is key with getting kids (and adults) to think, problem solve and learn how to ask more questions. In terms of treating it as PLAY, I had the most fun with my kids. Oh, and the answers I got ........!

Be ok with foundering.

Don't worry about not getting it right 100 percent of the time and failing. After all, failure is the new black -- if you haven't heard. To become better at asking questions you must be willing to test-drive different approaches. I think this is akin to trying out different types of cues while coaching exercises. What’s salient for him may not be salient for her.

Adopt the mindset that change is good.

I think in order to ask better questions you need to adopt the mindset that change has the potential for more good than bad. Many people seem to be change averse. What if we created a culture of questioning?

As David Bowie (RIP) said “Turn and face the strange”


Inherent in the quest for behavior change is motivation. So, why am I motivated to get better at asking questions?

I often find myself feeling overwhelmed by the vast amount of things I don't know YET and the plethora of information there is to learn. So, that's part of it: I want to know more. I want to know more about what I don't know. By asking better questions I can prioritize subjects that are most relevant to my life. I can further develop the principles that guide my decision making.

Central to my life are my relationships: family, friends, colleagues, students and patients. Each and all of these will benefit from better questions.

Last but not least, I am intimately aware that the most difficult questions to ask are those we ask of ourselves. They are the ones that are easiest to ignore and likely the ones that are in most need of addressing.

I bought myself Ryan Holiday's The Daily Stoic Journal: 365 Days of Writing and Reflection On The Art Living. When I first looked at this book I thought; cool here is an active way to engage in stoic philosophy. Then I looked at the questions the journal asked to prompt reflection and I felt a visceral flood of "Aw, hell no".

I know that feeling, "Aw, hell no." It's one of the ways fear creeps up in me and can easily lead to avoidance. So, the best reaction was to press "ADD TO CART" and I bought it.

Here are a few sample questions:

· Where am I standing in my own way?

· What is the harder choice I’m avoiding?

· Do I rule my fears, or do they rule me?

· How will today’s difficulties show my character?

We spend so much time in our lives trying to feel comfortable. Focusing on things that give us a sense of reward. We do this in relationships, with eating, career decisions, exercise and hobbies. Asking questions like those above doesn't feel comfortable but it results in honest, deep reflection, which I believe is part of living a better life. It's part of Leveling Up!

Better questions -> better answers -> better relationships -> better life

Level Up!


"Always the beautiful answer who asks a more beautiful question."

--E.E. Cummings

“Great questioners keep looking – at a situation or a problem, at the way people around them behave, at their own behaviours. They study the small details; and they look for not only what’s there but what’s missing”

-- Warren Berger

"Ask yourself an interesting enough question and your attempt to find a tailor-made solution to the question will push you to a place where pretty soon you’ll find yourself all by your lonesome – which I think is a more interesting place to be."

--Chuck Close

"I never learn anything talking. I only learn things when I ask questions."

--Lou Holtz

“He who asks a question is fool for five minutes. He who does not ask a question remains a fool forever.”

--Chinese proverb

Resources on Questioning (listed in order of my recommendation):

A More Beautiful Question: the power of inquiry to spark breakthrough ideas

by Warren Berger

Improve Your Life by Improving Your Questions: The Knowledge Project: A Podcast by Farnum Street (Shane Parrish interviews Warren Berger)

Ask More: The Power of Questions to Open Doors, Uncover Solutions and Spark Change by Frank Sesno

Words That Work: It's Not What You Say, It's What People Hear

by Dr. Frank Luntz

The Coaching Habit: Say less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier


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