Deeper Questions

🔗This post contains Amazon associate links (links marked with Aal in parentheses)
🌊This post is part of this year’s ongoing depth study
🧩This post continues the discussion from Deep Questions posted on April 19th

Deeper Questions II by Maria L. Berg 2025

This year’s depth study hit a bit of a snag when I came to the conclusion that to deepen my thinking and writing I need to ask deeper questions. At the end of my post “Deep Questions” from April 19th, I proposed generating questions and then measuring how deep they are from how answering them rated on my depth scale I created for “Drawing Depth Data.” But when I went to generate deep questions, I felt like I didn’t exactly know how. I realized I was going about things a bit backwards: How could I measure the depth of a question from its answers, when the depth of the question is the answer? The deepest questions may not have any answers, only lead to more questions.

Table of Contents
What are Deep Questions? • Deep Questions Mindset • Generating Questions Evaluating for Depth • Deep Questions in Action • Further Reading

What are Deep Questions?

Deep questions are open-ended. They cannot be answered with Yes or No, or a one or two word answer. Deep questions push past the surface data of things and events to the whys and hows. Deep questions ask about underlying causes, probe the subconscious, and look for the unseen connections.

But how do we generate these deep questions? Nothing I read in books or online gave me a direct answer to this question. I was looking for the rules for constructing deep questions. I wanted to find a secret formula that would tell me how to ask deeper questions, but instead I found advice for changing my mindset.

Deep Questions Mindset

In the book Questions Are the Answer(Aal)by Hal Gregersen, he recommends that we immerse ourselves in situations where we feel:

  • less right
  • less comfortable
  • less compelled to speak

His ideas reminded me of living in a new country: being hyper-aware, all my senses heightened, constantly trying to figure things out from the slightest clues. He says if your willing to be wrong, uncomfortable, and reflectively quiet, your questions will multiply and lead to deeper questions.

In the book Change Your Questions, Change Your Life(Aal) by Marilee Adams Ph.D. she says we have two mindsets: Learner and Judger. We have to move out of our judger mindset (while making friends with it) and into our learner mindset to get to “Question Thinking”(she trademarked the phrase question thinking).

She defines the judger mindset as reactive and automatic, possibility-limited, and inflexible. The learner mindset is flexible and adaptive, responsive and thoughtful, and sees unlimited possibilities. When we recognize that we are in judger mindset, she provides a list of “switching questions” to get to the learner mindset. For example:

  • What assumptions am I making?
  • Is this what I want to feel?
  • Is this what I want to be doing?
  • What am I missing or avoiding?

Over at Inquiry Institute, Marilee Adams’s website, she offers a couple blog posts on mindset.

Generating Questions

Once we’re in the a questioning mindset, one thing all of the resources I read recommended was to start by brainstorming a whole lot of questions. In Questions Are the Answer(Aal), Hal Gregersen calls it Q Storming. He recommends setting a timer for four minutes and writing down every question that comes to mind. He sets a goal of at least fifteen to twenty questions.

Another thing they all have in common is to write down everything with no judgement. In the instructions for Question Formulation Technique, or QFT at the Right Question Institute website it says:

  • Ask as many questions as you can.
  • Do not stop to discuss, judge, or answer the questions.
  • Write down every question exactly as it is stated.
  • Change any statement into a question.

I was still having trouble generating questions, so I used some of the tools we’ve explored during this depth study to get me started:

  1. The Topoi from the Deep Questions post
  2. The Deep Knowledge Worksheet from the Depth of Knowledge post. The worksheet incorporates questions from Webb’s Depth of Knowledge and the Depth and Complexity framework.
  3. The Creative Question Starts from Project Zero Thinking Routines which I mentioned in the Deep Reading post.

Evaluating for Depth

Using all those tools to generate questions, I was able to generate seventy-three questions about depth and this depth study pretty quickly. But were they deep questions?

After generating all of those questions, I realized why I had been having so much trouble coming to conclusions about how to form deep questions. I had been asking What is a deep question? and looking for an answer, when a question was the answer all along. I finally re-framed my inquiry to What makes one question deeper than another? and I started to make progress.

First, I combined any questions that were asking the same thing in different ways which got my list down to around fifty questions. Then I picked out the twelve questions that I found the most interesting. Twelve questions that I thought were the deepest of the bunch.

Here are the twelve deep questions I came up with for this depth study:

1. What am I avoiding in my depth study? Why?

2. What has yet to be proven about depth? What is unclear, missing, or unavailable?

3. What depths do I want to explore but haven’t found a way yet?

4. What is the possible value and purpose that I want from this depth study? What are the possibilities of this depth study?

5. When do we recognize depth?

6. Where do we find depth beyond its physical attributes?

7. How would others approach this depth study differently?

8. What moral arguments could emerge from this depth study?

9. Who values and cares about depth? Who are the experts or stakeholders? Who or what is influenced by depth?

10. What assumptions am I making about depth?

11. What general statement, hypothesis, or main idea about all of the definitions and underlying structures of depth relate in a way to create a useful understanding of depth?

12. What analogies or metaphors could be used to compare depth to other things?

These questions are not in any particular order. You’ll notice that many of these questions are more than one question: I found that for some of my questions I couldn’t decide which way of asking was the deeper question, and couldn’t find a clear way to combine them, so I kept the related questions together. This is not a definitive list, but only a starting point. To continue my exploration, for each of my questions I need to ask: What is a deeper question than this? Why?

Looking at my list, I was surprised to see that most of my questions start with What. I found that strange when deep questions are about why and how. The first question start of Project Zero’s Creative Question Starts is just “Why . . . ?” My first question has a Why? at the end. So I started looking at all of my questions and they could all be followed by Why?

Exploring this idea, I came across Five Whys. Five Whys is an iterative interrogative technique used to get to cause and effect first described and used by Toyota Motor Company. Like a little kid asking why the sky is blue, each answer is responded to with Why? until getting to the root cause of a problem (or an acceptable answer). It is called Five Whys because the technique is to ask Why? five times, but it may take more or less iterations to get to the desired conclusion.

For our purposes, we may want to practice Five What’s Deepers along with our Five Whys.

Deep Questions in Action

Now that we have tools for generating and evaluating deep questions, and some ideas for how deep questions can lead to deeper questions, what’s next?

The next thing I did was see if my twelve deep questions were as interesting (and deep) when applied to another topic. I’m working on my prompt posts for this October’s Writober with the theme Our Deepest Fears, so I replaced “depth” and “depth study” with “our deepest fears” and was happy with the results. I can now use these questions for:

  • journaling
  • evaluating example poems
  • creating prompts
  • writing inspiration
  • guiding research for daily topics and themes
  • continuing our depth study during Writober

The resources I read recommend making a daily practice of generating questions. As with all things, practice leads to improvement, and daily question generation will keep us curious and aware of all the exciting things we don’t know. They recommend setting aside a designated time each day for silent contemplation. One recommended practice is during this time: Note how you are feeling. Q storm for four minutes. Evaluate the generated questions. Choose up to three questions to guide your inquiries. Note how you are feeling again.

Further Reading

Books

Questions Are the Answer(Aal)by Hal Gregersen
Change Your Questions, Change Your Life(Aal) by Marilee Adams Ph.D.
The Book of Questions(Aal) by Pablo Neruda (poems)

Websites

Right Question Institute
Harvard’s Project Zero’s Thinking Routines Toolbox
Inquiry Institute

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For this post I tried a new format including a Table of Contents with jump links for the different sections. What did you think? I’m testing it out for the Writober prompt posts. Do you like it? Please let me know in the comments.

Published by marialberg

I am an artist—abstract photographer, fiction writer, and poet—who loves to learn. Experience Writing is where I share my adventures and experiments. Time is precious, and I appreciate that you spend some of your time here, reading and learning along with me. I set up a buy me a coffee account, https://buymeacoffee.com/mariabergw (please copy and paste in your browser) so you can buy me a beverage to support what I do here. It will help a lot.

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