What is a questionologist? (and how can one help you?)

By Laura E. Kelly

When you’re innocently finishing up your breakfast and you see a group of women across the room putting their heads together while looking at you, you know something is up. You just hope they aren’t talking about the way you’re scarfing down your delicious granola.

The group beckoned me over to their table, where Ann was sitting. I noticed everyone smiling nervously while looking expectantly at me. I only had a moment to think “Uh, oh,” before Ann asked if would be willing to do my Flash Workshop presentation 15 minutes from then. I had been scheduled to be the second speaker on this first day of the 2018 Women at Woodstock retreat, but was now needed to pinch hit for lead speaker Alice March, who needed to switch her start time with mine because, well, no one had woken her up for her granola and she was running late.

Hey, anything for Ann and Alice. Plus, I was happy to step in because I knew that I had a great icebreaker for the 20+ Woodstock retreat women—some of whom knew each other, and others who didn’t.

I was at WAW to enjoy the four-day retreat like everyone else, but also to spread the word about the power of questions—a skill that we all possess but barely use in our autopilot daily lives. I co-own an editorial business with my husband, Warren Berger, who’s written a number of books about innovation and creativity, with a recent focus on questioning. By dint of working with Warren in researching, editing, and marketing THE BOOK OF BEAUTIFUL QUESTIONS, and A MORE BEAUTIFUL QUESTION before it, I had become a questionologist like him.

And so I found myself on 9 am Friday, Oct. 12, in the beautiful, light-filled Lifebridge meeting room in front of a bunch of sleepy women who were no doubt wondering, “Questioning? I need answers, not questions,” but were too polite to say so.

Me waking up the 2018 WAW crowd about the power of questioning.

First, we talked about who’s the best questioner out there. The mothers in the room guessed correctly:

300 questions a day for her mother!

Then the life coaches and teachers in the room nodded knowingly as I spoke about how the most famous “experts” in the world are people who are actually lifelong learners and questioners. The rest of us, however, ratchet back the questioning around the time we go to school, where answers are what wins us good grades and teacher praise. Questions are often discouraged by our judgmental peers and our time-crunched teachers, and, later, by our results-driven bosses.

Yet questions are a proven key tool for connecting, deciding, creating, leading and just plain living a full, growth-oriented life. Questions are something we need to cultivate.

The goal for my talk was to quickly reintroduce people to the power of questioning. I told everyone that I was going to touch on two big categories of questions:

  • The questions we ask others
  • The questions we ask ourselves

Working on Warren’s book, I had learned that questions are a great way to connect with someone and get to know them fast—a perfect thing to kick off a retreat!

I asked everyone to get out the “Q card” in the folder I’d handed out; it was titled “Questions to ask instead of ‘How Are You?’ and instead of ‘What Do You Do?’” I asked each person to find a partner, pick a “connect” question off the card, listen to their partner’s answer, ask follow-up “And what else?” questions, and then turn over the questioning to the other person.

When I said, “…And go!” the room sparked into animated conversations. Being forced to turn to the person next to you and ask a rather bold question like “What’s the best thing that happened to you this week?” or “What are you most passionate about?” turned out to be just as energizing an icebreaker as I’d hoped.

How to Craft Your Own Beautiful Question

After that fun exercise, we moved on to the best questions to ask yourself. To be honest, we barely touched on that topic—THE BOOK OF BEAUTIFUL QUESTIONS has hundreds of great questions to ask yourself to check your biases, figure out what to do next, be more creative, connect better with friends and family, and be a more compassionate and effective leader.

In the interest of time, I zeroed in on helping attendees start formulating their own “beautiful question,” a question that is ambitious yet actionable and begins to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change.

There are as many personally meaningful beautiful questions as there are people, but just to get things started, I suggested a framework for building a beautiful question, using three focus questions.

A) “What is one of your superpowers?”—which could mean something you enjoyed as a kid, or that you really enjoy doing now with no pay or incentive, or something that people often tell you you’re good at that you take for granted. (You know—the compliments that you wave off because, of course you can do that, can’t everyone?)

B) “What change would you like to bring about?” Here you’re trying to identify a problem in your life you’d like to solve, a cause you’d like to contribute to, or perhaps a new idea you’d like to share with the world.

C) “What might stand in the way of this idea?” Could be money, time, ability, don’t know how to start… All the obstacles we let divert us from real progress and change.

Then I suggested that people lead off their beautiful questions with the three open, expansive, and action-oriented words “How might I…”

Finally, I threw out the caveat that made all the difference for me when I was formulating my beautiful question:

“Do not think about how you would answer this question or even if you can answer this question. Your job today is just to formulate the question. Your question will not be answered overnight. You have to live with it and address it over time… The answers and actions that are meaningful to you will emerge.”

So, the framework for a beautiful question might look something like this:
How might I apply A (superpower) and accomplish B (solving problem) while making sure I deal with C (obstacle)?

And begin!

As the women began working on their beautiful questions, the focused brain energy was palpable in the room. I could see that some women already knew exactly what their big question was. Others were using the framework to begin building their question.

We only had 10 minutes to begin the work of crafting a beautiful question. When the time was up, I asked if anyone wanted to share their question. Nobody was ready at that moment to go public, so I asked people to take their question home with them, work on it, think about it, and begin acting on it, by chipping away with little actions to nudge them down the path to answers.

I also meant to mention that keeping the question front and center ensures continued action. Some people put their question on their bathroom mirror or on their car dashboard. I have my question handwritten on a post-it stuck on the right side of my computer screen, leading to weekly big and small actions to address it.

The power of sharing your question

Sharing your question with others is a key feature of using questions to tackle your challenges. Unlike resolutions and declarations, questions by their very nature are engaging and shareable. Upon hearing a question that begins “How might I…,” listeners become intrigued and might even offer some good ideas to help you tackle your issue.

So now I’d like to ask the readers of this post to consider sharing their beautiful question with the rest of us—and this also goes for readers who weren’t at the 2018 WAW session. As I said in my talk, there is no right or wrong beautiful question, only one that is meaningful to you. And since beautiful questions should morph and grow over time it’s understood that this is just the first iteration, ready for additions and tweaks (and even wholesale redo’s) down the road. My current beautiful question is not the one I started out with.

I will start the ball rolling by sharing WAW attendee Brenda Rush’s beautiful question that she kindly wrote on the big pad of paper at the front of the room for us all to read:

Thanks, Brenda. That’s a classic multi-part beautiful question, with many components to take apart and explore. It’s one I hope you will spend time pondering and pursuing over the next year. I fully expect that you’ll be amazed where the pursuit of your question will lead you.

Anybody else ready to share her question here on the WAW blog? I’d love to read them, and probably others would, too. I’ve listed mine below in the comments to get the comments going.


THE BOOK OF BEAUTIFUL QUESTIONS has 40 sidebars of themed questions. Forty might not seem like that many, but it adds up to more than 200 questions, and I can vouch firsthand that they required a lot of research, interviews with experts, and time to compile & curate.

I recently designed those sidebars as portable postcards. Someday maybe they’ll be preprinted in a cool card deck for sale on Amazon, but right now they are a free downloadable gift for readers of the book… and for you! Click here to download 40 cards of themed questions from The Book of Beautiful Questions.

Even if you don’t think you’ll use the cards, take a quick look at that link to see the fun list of questions, which range from “If you simply can’t find the time to be creative, ask yourself these 5 questions” to “Questions to make someone like (or even love) you.”

Book marketing section of this post (you knew it was coming)

You can find the full stories behind the questions on these Q cards in The Book of Beautiful Questions, which just went on sale on 10.30.18 and is available in hardcover, ebook, and audiobook format, for all the multi-taskers out there.

An early heads up: BloomsburyUSA isn’t offering any discounts on the new book just yet since it’s brand new, but on November 8 through December 3, Bloomsbury is sponsoring a special ebook promo of Warren’s original question book, the bestselling A MORE BEAUTIFUL QUESTION, on sale for $1.99 on Kindle, NOOK, Google Play, and iBooks during those four weeks. So bookmark those dates and pass the word along.


If you need more incentive to come up with an ambitious but actionable beautiful question for yourself, click here for a short list of beautiful questions that sparked million-dollar businesses.

Laura E. Kelly is the creative director and partner with author Warren Berger in WBLK Media, Inc., a media consultancy that specializes in words and images, specifically books, articles, book proposals, and websites for creatives. Their most recent co-production is the new book, The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead. She led the workshop, “Building Your Big Beautiful Question” at Women At Woodstock 2018.

One thought on “What is a questionologist? (and how can one help you?)

  • November 5, 2018 at 11:22 am

    So here’s my Beautiful Question 3.0, as promised: “How might I brush up my skills of what I loved to do as a child—writing and drawing—without spending a lot of money, while bringing more meaning and purpose into my life?” Pursuit of that question most recently prompted me to raise my hand to volunteer my writing and graphic arts skills to a few local nonprofits and first-time candidates. This led to me teaching myself even more new skills (I was doing only digital design and writing, now I do I print design as well) while enjoying a positive feeling of “making a difference.” The bonus is that pursuit of this BQ introduced me to a bunch of nice new people in my community.


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