Learning to Ask Good Questions, All Over Again

Learning to Ask Good Questions, All Over Again September 14, 2018

For a long time, I prided myself in my ability to ask good questions.

Wednesday afternoons are my favorite question-asking time.

Call it the reporter or the curious human in me, I knew how to so engage in conversation that I could draw answers out of those labeled most unlikely to talk. I was the Oprah of my imagination and sometimes even of coffee shop conversations.

After all, before I became a writer, I was a high school English teacher, and after that a director in a non-profit outreach organizationSo, for twelve years much of my job revolved around knowing how to ask good questions.

Every so often, I’d ask a student if they wanted to play twenty questions.

“You mean like the board game?”

“Not exactly,” I’d reply. “This is more like, I’ll ask you twenty questions about your life and you get to answer them!” Generally, that was all I needed to say before their eyes lit up: Yes, I want to talk about myself, they’d shyly reply. Yes, I want you to ask me these questions. Yes, I want to play this really silly, but potentially really fun “game” of yours.

So we did. And usually, we’d never even get to all twenty questions because natural, normal conversation found its way into our time together.

But then, it’s like I lost my question-asking mojo.

I mean, sure, I could still be a good question-asker if I had to, if I was interviewing someone for an article or sitting across the table with a friend at a coffee shop.

But it’s as if I only knew how to ask good questions when I was getting paid for it or trying to be a good friend …so guess who oftentimes got the leftovers of my tired, same ol’ same ol question-asking self?

My family.


I think the story went something like this: once upon a time, dating turned into engagement, turned into marriage, and the endless string of questions I used to ask my husband turned into an assumption that he would freely share about his day without me having to draw it out of him.

He and I had to work hard to learn how to ask good questions of each other all over again – but it’s something we’re still learning to do again with our boys.

We can’t just show up at the dinner table and expect them to gab about their day without a little direction from us, just as we can’t expect a full report of the day’s findings at Kindergarten by merely asking, “Hey buddy, how was your day at school?”

Maybe that works with some kids, but it hasn’t necessarily worked with our boys.

Because sometimes learning how to color outside the lines means learning how to ask questions all over again. 

I say this in a most literal and a most figurative sort of way.

With my kids, I’m following the lead of a handful of parents who’ve paved the road ahead of me, instead asking questions like, “Who was kind to you today? Who were you kind to today? What made you laugh? What made you happy?”

And lo and behold, it’s working. 

It’s also not all that different when it comes to the rest of life. I’m learning how to ask questions about the things I don’t always understand and listen for the stories I haven’t always taken the time to hear. I’m learning how to question why I say the things I say, things I’ve sometimes never really thought much about but flippantly let roll off my tongue. I’m learning how to question systems that benefit me and don’t benefit others, just as I’m learning how to look at God through a lens of justice, sometimes, it feels like, for the very first time.

After all, a genuine curiosity lives within me, but sometimes I have to remind myself of its insatiability.

Now, if you’ll excuse me, I’ve got some questions I need to ask.

What questions are you asking these days, of yourself, of your religion, of your family and of the world around you? 

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