Which Question are You? On the Art of Asking

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It’s no accident that one of Instagram’s most popular features enables followers to ask questions of each other. Everyone loves being asked about themselves, not necessarily out of pride, but because, as human beings made for community, we naturally feel most supported when others express an active interest in our lives. Practicing the art of asking—in addition to truly active and empathetic listening—may become a powerful way to develop this interpersonal curiosity through conversation.

What. When. Where. How. Why. Who.

It seems that there are two key groups of questions, the first being the details: what, when, and where.

And the second group being the development: how, who, and why.

I have been trying to ask more questions in general, but it recently occurred to me that it’s not always about asking more questions or even about asking better questions, but about asking the right kinds of questions.

I feel best known, for instance, when people ask what I am working on, what I like to do in my free time, what I hope for in the next year. And I feel most valued when people seem genuinely interested and appreciative of what I do. Likewise, I tend to ask people what they are working on and am more prone to ask about people’s projects and careers than their feelings, though I am doing my best to grow in this area.

Similarly, I also tend to ask when and where because, being a planner and something of a perfectionist, I like to know what to expect and how to best be prepared. As a result, I often ask people where they like to study and when I can expect to see them again; for me, these questions are about forming a solid plan to facilitate future meetings and foster companionship.

Rather than simply recognizing my preferred questions and forcing other people to cater to my personality, though, I hope to use this realization to better engage with others in dialogue and relationship. Recognizing that someone I love is more of a “who/why” questioner will help me ask better questions about his/her relationships, motivators, and goals, ultimately deepening our communication and understanding.

Again, this is not a comprehensive theory by any means, nor will I create a catchy quiz to help you all sort out new identities based on the 5 Ws and 1 H (there are too many competing numbers and letter combinations out there already anyway). I do think, though, that the following may prove helpful to those of you who, like me, find yourself struggling to know what to say—or better, what to ask.

Questions and Tendencies:

What: From my personal experience, people who ask what-based questions tend to be focused, task-oriented, and pragmatic. They want the facts and checklists and step-by-step plans for success. However, these people are likely to also be highly-conceptual, potentially more interested in understanding theories and projects than relationships or emotions. To encourage these individuals, consider asking about their current pet projects, and offering positive comments about their work.

Where/When: I’ve grouped these together as they are both centered on planning and preparation. Again, from my experience, these askers are often regimented individuals who value foresight and preparation. Alternately, these individuals may be prone to worry; asking about time and place may be a way of creating a less-anxious future. Continually asking where or when-based questions may be a way of easing the stress of scheduling, securing quality time in relationships, and/or voicing expectations.

Who: I love people who ask who-based questions because they inspire me in their care for others. These askers are likely very caring and relational, even asking about the friends of friends of friends in an effort to get to know someone through their social circle. They will likely want others to show the same care for their community and appreciate it when others check in on their loved ones as well. These individuals thrive on questions that foster deeper companionship and a broader sense of community.

How: There are two types of “how” questions: emotional and technical. Those who ask “How are you?” and follow up with specific inquiries about a person’s wellbeing are demonstrating a more emotionally-aware version of how-based questions. More akin to when/where/what askers are those who ask “How?” in order to gain practical insight into the method by which something is accomplished. Both versions, however, can evidence an intrinsic curiosity and desire for deeper knowledge which I admire. (Interestingly, “knowledge” itself carries a similar dual nature as we can know about a person or thing, or genuinely seek to know a person or thing.) Askers of both types will appreciate reciprocated curiosity and active listening.

Why: More than once, I’ve been frustrated by someone daring to ask me “Why?” because this question cuts to the heart of the others. Those who are careless with it may come across as cynics, while those who never ask it may lack discernment. Those who ask why-based questions often are value-driven, desiring to act in accordance with their well-considered ideals. Asking why-based questions of another person can either express interest in or challenge their fundamental motivations, so it must be approached with sensitivity. However, this may render “Why?” the most telling question of all, and those who ask it tactfully may learn a great deal about others and themselves.

So, what do you think of this idea? Or, maybe, who do you think of when reading this? Or, where/when do you see this being applicable in your life? How do you think this little thought-project may be helpful?

For once, the “Why?” of the matter is simple. Why write or read or share this article? Why consider the different ways in which we ask questions?

Why? Because, I hope, we desire to be better equipped to communicate effectively, care personally, and connect meaningfully, and asking the right kind of questions might just be a good way to start. We might practice leaning into the questions that we naturally ask well—with good questions leading to more, deeper questions—as well as broaden our curiosity to encompass the full range of asking.

2 thoughts on “Which Question are You? On the Art of Asking

  1. Beck February 23, 2020 / 9:47 pm

    So I tried to comment, WordPress LOST the comment, and deleted it. So Let me try to rewrite what I said initially…

    Yes to ALL of this, firstly. As a fiction writer, questions are the most important part of the writing process to me. Especially the “Why” questions. “Why” questions push people forward, and – like you worded it – allow them to “learn a great deal about others and themselves.” I posted that one article about world-building a long while ago, and that is the driving force: Why? “Why” does a hobbit live in a hole? “Why” is this boy going to a wizarding school? “Why” is this ship on a journey to parts unknown?

    That Why question, man, it makes the world turn. Just think of all the “why” questions that led to so many inventions and discoveries. “Why” can’t we have light at night to continue working? “Why” does it take three seconds for this apple to fall from the branch to the ground? “Why” can’t we build a machine that lets us fly like the birds?

    In my opinion, the best Why question is “Why not?”

    Liked by 2 people

    • Ryanne February 23, 2020 / 10:28 pm

      Oooh the tables have turned. You’re brilliant, as ever.

      Like

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