Jeremy Statton

Living Better Stories

How to Ask Better Questions

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Do you know how to ask good questions? Really good questions?

It may seem like a dumb question, but most of us don’t. We learned the 5 questions words in our high school English class. But we haven’t learned how to use the words well.

Our questions tend to be superficial and not deep. Passing and not engaged. We often stop asking them way too soon. We often stop right before the answers become interesting.

When we learn to ask better questions, we can stumble upon amazing discoveries. Perhaps even the opportunity of a lifetime.

Photo by Clarkston SCAMP (Creative Commons)

Discovering an Opportunity

I have a friend, Stan, who works in a marketing department of a large medical device company. He loves his job and it shows.

One of his strengths is asking incredibly good questions. I have watched him work and he never hesitates to take the next step. All he needs is a place to dig.

His questions really make you think. He is persuasive not through argument, but through his question asking. It is amazing.

His skill has even opened doors that he didn’t know existed until he asked.

One day while traveling he decided to ask the man sitting next to him some of these questions. Many of them were routine, but he wasn’t just being polite, he really wanted to know the answers.

The responses created an opportunity.

The man seated next to him was an owner of a NASCAR racing team. As they talked further and more questions were asked, the owner asked Stan a question in return.

He was impressed with Stan’s ability to connect and unify people. He asked him to be a consultant to his team.

This isn’t a position that you can apply for. It isn’t posted on Craigslist. Good luck even meeting someone who knows someone who knows someone who owns a racing team.

But this happened for Stan. The opportunity sat hidden next to him disguised in a stranger. Through his better questions, he was able to unearth it.

Asking Better Questions

Here are 5 quick ways to make your questions better.

1. Listen. Most of us are so distracted we pay little attention to the people around us. When we listen, we actually learn who people are. We discover what makes them tick. We learn what we should really be asking.

2. Care. It isn’t enough to listen, we also need to care. If we find the person in front of us genuinely interesting, then our questions will get that much better. Our minds and especially our imaginations become engaged when we care.

3. Be Persistent. Don’t stop with one question. Keep going. Better questions often develop only after you have asked a few bad ones. With the bad ones, you learn information that help you discover what a good one might be. This isn’t a license to be annoying. But please, don’t give up easily.

4. Don’t Assume. I wonder how many really good questions were not asked because false assumptions were made. I wonder how many opportunities have been lost because these better questions weren’t asked. Assume nothing. Ask everything you think might be important or relevant.

5. Explore. Most of your questions are derived from your own perspective on life. If you expand your personal life experiences, your ability to ask questions will improve as well. Don’t settle for what you know how about something right now. Learn more. Read. Travel. Explore. Experience.

Homework Assignment

Asking better questions is like everything else in life. It takes practice. Try something new this week. Start asking questions.

The next time you meet someone new, ask them at least 5 questions. One beginning with each of the 5 question words.

  • Who?
  • What?
  • When?
  • Where?
  • How?

If you only ask because of the assignment, then you will fail to discover the magic of asking the next question.

But if you ask out of genuine interest and curiiosity, then I guarantee you will find something even better than a consulting gig in NASCAR. You will discover a new friend.

What helps you ask better questions? Have you had an opportunity develop just because you asked the next question? Share with us in the comments.

About Jeremy Statton

Jeremy is a writer and an orthopedic surgeon. When not ridding the world of pain, he helps you live a better story. Follow him on Twitter or Facebook or Google +.

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29 Replies

  1. Well said.  Showing up truly curious and caring makes all the difference.  Teaching Socratically is also incredibly powerful.

  2. I agree. some of the lessons best learned were ones that I was allowed to investigate and discover through asking questions.

  3. I find asking questions that cannot be answered by a “yes” or “no” answer creates the opportunity for great insights and connection.

    Instead of asking someone if they had a good day, ask them “What was the most exciting thing that happened today?” It forces the person to think about it and not answer with a pat answer.

  4. open ended questions do create more content. I find I have to start with simple “yes/no” questions first to get people warmed up though.

  5. Joe – This is especially true of my kids. 

    In a world of communication-by-text-messages, young people seem to be losing the skills needed to have a meaningful conversation.    Open-ended questions are a great way to help curb the “yes” / “no” replies.

  6. Great tips, Jeremy.  I’m going to print your post and tuck it in my ‘good ideas’ folder.

    I think some of these same ideas can be used for writing blog posts, too.

    Thanks for the help!

  7. It is all about asking open questions, that allow the responder the opportunity to give detain outside of yes or no.  The prompts that you post are essential for finding the story. 

    Having read your comments, starting with yes/no can be useful, but actually it is surprising just how much people will tell you with an open question if asked that first.  It often depends on context though, what you are asking, and why.  Do you have an agenda in your questions, other than to hear the persons story?  Our body language plays a huge part as well.  Do we look people in the eye when we speak to them, do we make them feel respected, do we allow them time to answer, how do we listen, are we making notes, or recording, or are we filming.

    A brilliant technique for asking questions especially tough one’s, is to compliment the interviewee on something about their appearance, what they are reading, something personal to them etc this really sets them at their ease, but it also can set them off guard which allows the tough question to be answered most honestly, and often without spin, which is essential for news tv or getting a scoop, if that is what you are trying to do, say writing for a paper of something like that

  8. Mark Dutton

    Great Post Jeremy! So simple but so foundational.  I am actually a decent question asker. I love getting to know people and learning from their experiences.  These opportunities present themselves often as I fly a lot for work.  One thing I have noticed though is even though I am decent at it and an I enjoy it, is that sometimes my laziness and self absorption get in the way. Conviction overtakes me as I sit next to someone on a 6am flight and all I want to do is close my eyes and think about how tired I am. Not that it is bad to rest… just that my attitude is I don’t feel like trying….

    The thing is I never know how that conversation will affect that person or myself that day. Whether it is just encouragement, a chance to share the gospel, or a great networking opportunity, I never know what I am passing up by not at least greeting the person next to me with a compassionate and genuine hello and introduction. Thanks for the reminder to be faithful!

  9. I know people like you. I am not one of them. I have never been a great question asker, but I want to be. Althought I wouldn’t blame you for taking the nap at 6am.

  10. Great tips. People love to talk about stuff they love.

  11. You’re dead on Michael. Text messages and Instant Messaging systems have destroyed many a meaningful conversations. It seems most want a quick message and be done with it. No more investment needed.

  12. I’m naturally a bad question-asker but I’ve been practicing and (sometimes) seeing improvement. I also grew up with a father who asks “a few” questions upon meeting every stranger, so I suppose I wanted to steer away from that annoyance. I love your reminder that the next opportunity could be beside you disguised as a stranger.


  13. Being a rather…introverted…individual, asking a lot of questions was always difficult for me, but something I’ve slowly been working on…it definitely helps to get to know someone better and when people feel like you’re genuinely interested in what they have to say they are more likely to trust you, but asking the right questions is important too, don’t just ask them stuff that makes it seem like you are trying to get something from them!

  14. What a great topic and reminder. Being able to ask good questions is so essential. This goes with caring, I would add to always bring value to the conversation. When talking with someone I always try to bring value to them and the conversation. An example is that I might suggest a book or blog that would help them.

    Great post.

  15. From a fellow introvert I understand where you are coming from.

  16. there is a balance between being annoying and persistent asking.

  17. Great post, Jeremy. This is something that I definitely need to work on, to practice. I usually stop after a couple of questions, afraid of being too intrusive. But you are right, I wonder how many opportunities I might have missed!

  18. When Stan told me about his gig, it blew me away.

  19. Great post Jeremy. I like #5 esp. It’s true that we often see life as “we are”, our experiences are shaped by the person within.

    There is a saying in Africa “he who does not travel thinks his mother is the best cook”

    If you never venture beyond ur comfort zones, you never stretch, never grow.

    Experiencing new things stretches you, emboldens, makes you curios.

  20. Indeed. It’s a very fine line.

  21. Some random thoughts:

    Don’t ask questions like you may have been taught in school to do. Maybe it was just me, but teachers in my day & area had this funky idea that asking questions, even when you knew the answer, was important … but never said why. More often than not it turned into great fodder for the cruelty of elementary school classmates teasing you about what you didn’t know.

    • Don’t go into “interview mode,” like the person is there to be asked questions … unless, of course, you are interviewing someone, or if the person seems to enjoy that mode of thought. It’s often not a good “cold starter.”

    • Be sensitive to the other person. Some people are true introverts, and some suffer from a medical condition known as Social Anxiety Disorder. Some people are hurting so deep that they cannot let it out for fear of breaking down in tears or anger.

    • If the person seems to be a clam, pray about sharing a bit of your own story. I recall Anne Jackson relating a story in her book, Permission to Speak Freely, about just broad-side opening up to this one person about her former addiction (or perhaps even current at that time, I don’t recall now) to pornography. It turned out the other person had the same problem. Through that chat the other girl started a ministry, Dirty Girls, that reaches out to and helps women who are addicted to porn.

    I have to agree wholeheartedly with your list, Jeremy. Listening is the big one, I believe. Sometimes a simple question or two can open the floodgates to stuff that could blow you away. That’s where listening in another sense — to the Holy Spirit — gets major-league important!

  22. Great saying. I might steal that. But is it insulting to your mother to travel?

  23. Thanks for sharing your thoughts, Joe. I really like that story about Anne Jackson.

  24. It’s not.. lol.

    When you say it in Swahili or other local languages, others understand you perfectly. 🙂

  25. Earl Richardson


    Every post here appears to be in the context of asking questions to other people.  But I suggest the most valuable questions may be the ones we ask to ourselves.   Because that is perhaps where the most self improvement comes. 

  26. Christine

    You are an amazing writer- So thankful I found your blog!

  27. I like tip number one. Listen. Rather than rigidly sticking to an agenda, by asking questions that are based on what has already been shared will lead to more meaningful conversation.

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