Practice Asking Questions

Reframing questions through a CP lens to get you quickly to the "So What" of the matter. My thoughts, here.

A few years ago, around the holidays, my family and I went through a big box of old home videos. I’m one of four girls, you can imagine the endless reels of dress-up, performances , and admittedly, some fights over American Girl Dolls or something of that sort that my mom was forced to sit through and film. In one of the videos, my older sister owns the frame, twirling in a dress in the living room of our childhood home—when suddenly the camera starts shaking and the sound of heavy breathing from little lungs envelops the audio. The camera turns—a bit foggy—landing mere inches away from my 4-year-old face, and I say, “Mommy…whyyyyyyy doin’?”

To which my mom very plainly replied, “I’m filming you so I can have something to embarrass you with when you’re older.”

Reminiscing on this time in our lives, my mom recalled how I was an incessant question-asker—almost as if from the moment I could walk and talk, there was never not a pair of little feet padding behind her asking what she was doing, where she was going, and why, why, why. Like anyone, after being asked, “Why?” enough times, she would hit a dead end. Honestly, I have to give her some serious props here, because she is so the type to be a good sport and entertain my repeated questions, but once she had exhausted all of her ability, I’d be met with an, “I don’t know, Stella.”

Cut to the present day, not much has changed. Actually, I find myself asking even more Why’s and What’s than ever before. I’m in my mid-twenties (scary, yikes!), I’m living by myself for the very first time. I’ve been in the corporate world for five years—there’s actually never not something to be figured out. It’s exciting, energizing, exhausting…and very often met with an exasperated, “I don’t know, Stella.” Most of the time, said to myself in the mirror. I also work in an incredibly entrepreneurial office—discourse and questioning is not only frequent, but it’s demanded. We’re constantly asking ourselves what, when, why, and how.

Something I’ve found solace in as I navigate what it feels like to no longer be a rookie—both at work, and in early adulthood—is seeking information. About anything and everything. Yeah, yeah, knowledge is power and everything…but above anything else, in this stage of my life, being informed makes me feel grounded.

There’s a publication I’ve become completely enamored with that shares articles related to behavioral science, across all industries, and from incredibly interesting vantage points. As an alternative to doom-scrolling on social media during my morning commute to the office, I’ve begun picking a new article to read each day. A few weeks ago, my article of choice was by a sociology professor on the importance of framing questions through the lens of “How” rather than “Why”. She went on to suggest that asking why tends to produce an answer similar to my mother’s finite, “I don’t know.” If you ask why enough times, you’ll inevitably hit a brick wall rather than dissecting deep enough to get to the root of the question at hand. But if you swap out why with how, you’re more likely to be met with not only a more robust answer, but it will likely prompt deeper thought paths leading to the answer you may not have even known you were looking for.

The author gave a great example, which will round out what I’m trying to say: if someone were to ask you why you were at your current job, you might say, “It pays the bills,” or “It was the first role I was offered out of school and I’ve just been here ever since.” But if someone asked you how you came to work at your current job, your answer would probably be much more illustrative of why you do the work that you do.

At Tibi, I work in digital marketing and publishing. I’ve also supported our public relations team, production team, and wholesale team over the course of almost five years. I’m not a sociology professor, but having worked in varied departments at this company, I can certainly attest to the importance of practicing thoughtful question construction.

I remember when I first joined Tibi, my role was split between public relations and project management—but at the time, we were down a team member on the wholesale team, so I filled in for about six months. Back then, I had zero wholesale experience and hardly knew how to use Excel. I remember being so completely panicked by the task of compiling weekly selling reports—at first, they would genuinely take me days to complete, just for one of our account executives to flag all the errors I had made. You know that thing that happens when you ask someone a question in a loud room, and you can’t hear their answer, so you ask them to say it again, and then you still don’t hear them, so you just nod your head? That’s how I felt crawling my way through the first couple of weeks—a total crash-course. But in hindsight, I was asking the wrong questions.

“Why do we include last week’s sell-through %?” was probably answered with something along the lines of, “Because it’s helpful for Elaine to see the numbers week over week.” But if I could re-ask that question, I would have gained much more insight from asking, “How can last week’s sell-through % help me better understand what I’m looking at when creating these reports?”

Separately—but undoubtedly related—is the importance of posturing your mind to be open to answers that change the course of what you had planned, what’s easy, or comfortable. I so vividly remember just after I had passed my first anniversary at Tibi, Amy asked me a question—I think it was about the runway show—and, hoping to sound informed, I began my reply with, “Well, historically…” and she stopped me in my tracks. She said, “Wait, what do you mean by ‘historically’? This is your first runway show, so I just want to make sure I understand what you mean.”

To be clear, she was genuinely asking—and she made an incredible point that has stayed with me for years, and pops into my mind every time I encounter a new puzzle to be solved. Given that I actually do have legitimate experience now, it’s very easy to repeat processes simply because that’s how we’ve done things in the past. And it’s for this reason that I often question how I do things—how I plan out our social media calendar, how I tackle the production of a new book, etc. And when I question my methods, I could ask, “Why do we post the Curated Closets Instagram Stories every Friday?” and easily answer myself with, “Because that’s when we initially decided to post it.” But instead, asking, “How can we position Curated Closets on our social calendar to make the most sense?” results in changing the posting date from Fridays to Sundays, so our audience can get in the mindset of preparing their wardrobe for the week ahead, resulting in higher engagement (this is a real example, by the way—and if you’ve never checked out Curated Closets, there’s no time like the present!). Asking the “how” helps reveal when the original goalposts may have moved.

It’s no surprise to me that a sociology professor’s article on effectively framing questions would directly apply to the work that we do here at Tibi, and likely for many of us, in our personal and professional lives, as well. The beauty of mindset is that it completely transcends trends or aesthetic preference—Creative Pragmatists are not just “sexy” or “edgy” or “chic” although they very well could be one or all of these things. They’re independent thinkers who ask questions. They’re curious, clever individuals from all walks of life. And what’s even better is when a company has attracted a consumer base that shares the same mindset, you proceed with confidence knowing that you’ll all be on the same page and if not, highly respectful in the discussion to getting there.

In chewing on these thoughts and writing this out, it’s so clear to me that in its own way, Creative Pragmatism and behavioral science go hand-in-hand—and it’s not a practice that remains exclusive to a classroom, or even an office. So from one young professional hopefully to another, I urge you to begin practicing asking thoughtful and purposeful questions in every facet of your life. In the looming expansion of AI growing more rapidly than the human brain can even comprehend, navigating uncharted territory regarding global events, interpersonal relationships, and careers, and getting to know yourself as you come into your own, sharpening your questioning skills will allow you to reframe your thinking in ways that can help you enormously. If something in your gut is scratching at you to inquire further…then scratch, ask, reframe your questions, and listen.

Read “The Power of Asking ‘How?’” by Rene Almeling here