How to Ask Great Questions and Why It’s Life-Giving for All

clouds shaped like question marks amid a bright blue sky. Feature image for the article How to Ask Great Questions and Why It’s Life-Giving for All

Ever have 43 things on your to-do list, and instead of getting them done, you fill out one of those silly internet/Facebook questionnaires that ask great questions? You know, the kind where you check off books you’ve read, movies you’ve watched, states you have visited, favorite breakfast cereal, etc.

I am a sucker for them. I mostly don’t even post them, I just read and answer them. I have taken almost every personality test out there. (Enneagram 7 here with a strong 8 wing, ENFJ). I read somewhere that people take personality tests, even the bad ones, in hopes of learning something new about ourselves.

Figuring Out Who We Are

enneagram article boardWe are all trying to figure out who we are… and maybe we will get closer if someone just asks us the right question. I’m not sure the answer to my being is in a quiz telling me what percentage of Betty White I am, but I still very much want to know. (The answer? 100%).

One of my least favorite things about therapy is when we get past the small talk and she just looks at me and waits. I know it is my turn to bring up the work. I’m a good student. I have prepared a list in my head of things I want to talk about and/or work on.

But sometimes I still hesitate.

I would rather she just ask me a question.

I know what I want to say. I am paying for this time, but at the moment I’d still rather answer a question than just tell.

Questions and Prompts Make It Easy

I have a friend who hosts what she calls a veritable feast in her bookshop once a month. She brings in food and she reads passages from a few books and you talk through a few simple questions or prompts at your table.

That is it. That is the whole format. Good food, a short reading and intentional conversation—mostly with strangers. It is like a book club without having to read a book first. Also, the story you find yourselves talking about is yours and your new friends’ more than any characters on a page. Each time I’ve walked away with new perspectives, insights, compassion and new questions rattling around in my head. You don’t need to go to a feast for this; just simply have a few prompts and a few people.

My favorite part from graduate school was that it gave me the opportunity to interview people. I sent emails to the smartest people I knew (and some that I didn’t know) and asked if I could meet with them. Eventually, I had questions that were coded and used for research, but at first I just asked the things I wanted to know.

What shocked me is that not a single person said no.

Every person, even people way above my pay grade, made room on their busy schedules and answered my questions. Many seemed to enjoy it and a few even took their own notes. I learned that people generally like telling their story and sharing their expertise.

…Even with Teenagers

Most Sunday evenings I help lead a group of high school girls at church. When I agreed to volunteer, I anticipated serving a meal, subbing when someone was out or something simple. Instead, I found myself each week leading a dozen high school girls all talking at once around me. I have plenty of experience from my years in the classroom with teenagers, but getting them to talk still felt intimidating. It took me a few weeks to find my rhythm. The secret was simply asking questions (and showing up with good snacks). Sometimes they were the questions off the handout, but mostly they were things like:

  • How was your basketball game last week?
  • How is your grandmother?
  • Chick-fil-A or Canes?

And we have spent entire breakout sessions simply answering our high, low, buffaloes. (High of the week, low point, and something random).

I have two teenagers of my own and I know better to ask how school was that day. The answer is always “fine.”

“What did you learn today?”

The answer is always, “Nothing.” (Lies.)

I’ve read the articles that have more specific suggestions: What made you laugh today? Who did you sit with at lunch? Did you help anyone today?

It worked a little bit when they were younger, but now those still get me an eye roll. My daughter will even occasionally ask if I read some article because a teenager loves to call you out. What they will do is answer outside questions. The more random the better.

We used to get texts that had weekly questions to ask at dinner. Things like:

  • What is the weirdest dream you’ve ever had?
  • If you could eat only one food for the rest of your life, what would it be? (Tacos, of course).
  • If you joined the circus, what circus act would you be?

Those texts stopped showing up each Monday on my phone. I forgot about them, but my kids surprised me and asked what happened to the questions.

The Secret to Sharing? Learn How to Ask Great Questions

Sometimes I think we are afraid to share without the ask. I’m a pretty terrible listener. (I’m forever working on this). But I’ve always believed in the gift of going first (sharing, inviting, kindness) and now I am learning the value of the gift of asking.

Questions are a springboard. A prompt or a question gives us an excuse to share. In most cases we don’t need an excuse, but somehow it feels less presumptuous than just telling. It is the gift that allows someone else to give themselves.

There is something even easier when the questions come from an outside source. Here a few of my favorites but it only takes a quick google search for age- or content-appropriate questions or would-you-rather scenarios.


Want more insight into who you are? If so, check out this podcast episode: Answering the Question “Who Am I?” With Meaghan Dawson – 116

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