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.

Now, “Which question are you?” sounds like a clickbait Buzzfeed quiz or, more likely, the personality test nobody asked for but everyone will still end up taking once the Enneagram finally runs its course. My goal in this post is not to create this sort of test or to sell you personalized coaching sessions, but I have put a fair amount of thought into the following project and it may be worth sharing.

You see, I am bad at asking questions. I either stick to small talk, go too deep all at once, or stay silent. Worse, sometimes I just ramble without asking the person I’m with anything, and I am fully aware that this comes across as uninterested or even selfish. I genuinely do want to get to know and care for people on a deeper level; practicing the art of asking—in addition to truly active and empathetic listening—is a powerful way to develop this interpersonal curiosity through conversation.

I’ve noticed in talking to my boyfriend that he always asks about the people in my life and how they are doing, whereas I am often much more concerned with asking what he is doing; he asks more relational questions while I ask more logistical questions. He also tends to ask “why” whereas I am more prone to ask “when” or “where.”

Similar patterns are observable in my other relationships. My roommate is excellent at asking how I’m doing and my mom is incredibly thoughtful in asking about who is involved in my life.

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.

Knowing which questions I tend to ask and which questions my friends and family wish I would ask has become something of an obsession lately. I have been trying to ask more questions in general, but it recently occurred to me that it’s not 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.