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Four Questions Deep

By Dave Stuart Jr.

I want you to try something with me this week: what if, in a conversation or two — with our kids, with our colleagues, with our spouses, with our students, with crazy Uncle Harry who you only see at Thanksgiving — we tried asking four questions in a row. “In a row” isn't the best way to put what I mean: picture each question as a shovel scoop; I'm talking about digging four times down into the same hole.

I'm sitting here trying to list examples and struggling.


  • Question 1: Hey Johnny, how was your weekend?
  • Question 2: You really enjoy that game, don't you?
  • Question 3: Um…?

What I predict is that, as I try to have a “Four Questions Deep” conversation this week, I'm going to flail around a bit.

Why try to go Four Questions Deep?

I think that asking great questions of someone helps us understand them. When I ask the right questions of my students or my own children or my colleague across the hall, I learn who they are. And, more often than not, when I ask the right question, they feel more understood by me. Great questions enhance both sides of a relationship.

Practicing the art of question-asking also has a humbling effect on us. (Think of humility in the C.S. Lewis sense: “thinking of yourself less and thinking of others more.”) Humility, as I've written before, makes us better and saner teachers.

And finally, I suspect that, if we do happen to have a conversation this week that truly goes four questions deep, that will probably end up being the most interesting conversation we have. Interesting conversations cultivate character strengths like curiosity and gratitude, and they probably just make us smarter, too.

Take a crack at it with me this week; let me know how it goes in the comments.


9 Responses to Four Questions Deep

  1. Shelly Smede November 24, 2015 at 9:48 am #

    Each question has to be inspired by the answer that comes before it:)
    Question 1: Hey Johnny, how was your weekend?
    Answer: Boring
    Question 2: What made it boring?
    Answer: There was nothing to do. Mom took my computer and the TV’s not working.
    Question 3: Would you like to go to the bookstore and pick up something to read for next weekend?
    Answer: I hate reading.
    Question 4: Why?

    I love this idea – I think I read about it in either The Innovator’s DNA or A Whole New Mind. Except they say go five questions to really dig deep. I’m going to do this all week. Thanks, Dave!

    • davestuartjr November 24, 2015 at 10:39 am #

      Shelly, I will have to check those books out. It didn’t seem like a novel idea to me when I wrote it last night, but I promise I’d not read or heard of those books prior to you leaving this comment. Thank you, also, for filling in my four questions 🙂

  2. Heidi November 24, 2015 at 11:05 am #

    My initial experiment went like this: I asked two students as many questions as I could think of. It wasn’t hard for me, these two were talkers, as am I. I had a conversation with them, that was more personal than academically based. Then told them what I was doing. I asked them how it made them feel to have me ask them questions (these are new students to me, I have only had them three weeks). They said it made them feel good, like I actually wanted to get to know them and what they do in their lives outside the classroom. This is my life-skills class, so I am going to include the “4-Deep” theory when we read the AOW about listening. I think this is easier for someone who is totally comfortable talking to strangers (as I am), as an extrovert. After this, another student approached me with a question, the original 2 students stayed by my desk and counted 9 questions that I asked the 3rd kid! Most people are cool with talking about themselves…especially 8th graders, so my sample may have been a little skewed.

    • davestuartjr November 24, 2015 at 1:52 pm #

      That is an excellent experimental report, HBonn 🙂 You got right on that! Thank you! 🙂

  3. Angela November 24, 2015 at 11:54 am #

    As an Instructional Coach the art of question-asking has to be exactly that, an art. In order to be effective and build trusting relationships with other teachers and staff I must be willing to go “4 questions deep” often more. Most importantly I must ask in order to listen. Actively listening and paraphrasing the response values the other person and demonstrates to them that I am not there to “fix” them or “ding” their instructional practices, I am there to support them and work alongside them through the highs and lows, and the mountains and valleys. Thank you amigo for putting this out there and challenging your readers to practice the art of question-asking and listening.

    • davestuartjr November 24, 2015 at 2:04 pm #

      Angela, thank you for sharing this. The best coaches seem to find a way to do exactly what you’re describing, offering explicit feedback when requested or needed. I hope you and your family are well!

  4. Kyle Fedderly November 24, 2015 at 3:24 pm #

    Love it, as always. I’m also struck by the fact that this is exactly how I get my students to elaborate in their writing. I have developed the habit of grabbing a chrome book and logging on to the same document a student is working on at the time and typing questions in a different font color where I want them to elaborate or clarify. They then highlight my text and replace it with their answer. Voila: elaboration. If I could get my students to do the same thing during peer-editing exercises, they should begin developing a better sense of where elaboration or explanation is required in their own writing. Thanks, Dave. Once again, you’ve helped me connect a few critical dots. Happy Thanksgiving!

  5. davestuartjr November 27, 2015 at 9:21 am #

    Kyle, this is a cool idea for advancing your students’ writing. Great teachers = great questioners.

  6. davestuartjr November 27, 2015 at 9:25 am #

    UPDATE: Asking more and better questions is proving to be an interesting challenge. There’s a social intelligence aspect of this that I think I’m hit or miss on — sometimes it’s not so great to keep asking questions. However, erring on the side of taking an interest in other human beings — that is what I want to do. I would rather be thinking less of myself and more of others than afraid of asking too many questions. Thank you, commenters, for the encouragement and keeping me on this thinking track over the holidays. Cheers 🙂

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