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How and Why To Ask Better Questions

| Molly Slicker |

As the world re-opens and we start to slip back into social settings, there’s never been a better time to reevaluate our everyday communication habits and patterns.


As an introvert who recharges by being alone yet actually enjoys socializing with friends and family, I have spent quite some time analyzing why certain social situations can be so draining for me. I’ve realized that it’s not necessarily the socializing that’s exhausting, it’s the type of obligatory surface-level social niceties our society has trained and applauded that takes the wind from my sails. I’m sick of small-talking with big-hearted, big-minded people.

Yes, small talk is polite and certainly has its rightful place and purpose. It can be perfectly fine and necessary, but we too often stay in the shallow end for too long. Many of us are still in the shallow end even with those we are closest with. Our time is finite and our relationships on this earth are the greatest things we can create while we’re here… so why shouldn’t we make things more intentional, more purposeful, more fun?

If one more persons asks “How was your quarantine?” as if we’re just returning from Summer Camp I might… I don’t know? Look into adult Summer Camps to get away from this ridiculous question. After almost 2 years of not seeing each other and experiencing some truly horrifying realities along the way, let’s be a little more thoughtful. Let’s ask better questions.

According to a study in Harvard Business Review, “Dating back to the 1970s, research suggests that people have conversations to accomplish some combination of two major goals: information exchange (learning) and impression management (liking). Recent research shows that asking questions achieves both.”Also… “In a meeting or group setting, it takes only a few closed-off people for questions to lose their probing power. The opposite is true, too. As soon as one person starts to open up, the rest of the group is likely to follow suit.”

I have always been interested in people. I’ve had friends call me before dates to hype them up and prep them with some fun questions to have in their arsenal should the conversation lull. At one point my family voted me the one they’d most like to bring on a road trip because I am always ready with a good playlist and a good set of open-ended questions. Most of us have probably heard of the now infamous — Modern Love piece from The New York Times “The 36 Questions That Lead To Love.” Yep, that was always my go-to for suitors and I highly recommend it as an excellent start to anyone on the quest for better questions.

For some, questioning comes easily. They may be naturally inquisitive with a higher emotional intelligence and ability to read people. Whether you’re a natural journalist or not, know that most of us just don’t ask enough good questions. We need to explicitly expand our interest in others and dig deeper. I will say, if you’re someone with a varying level of social anxiety — asking fun questions is a great resource to steer the conversation on a path you’re comfortable with. Win/win.


My best advice? Start light, adjust accordingly, stay open.

My Patron Saint of Goodness, Ted Lasso’s, best advice? Be curious, not judgmental.

Replace circling through the same old small talk with your loved ones and actually get to know them in ways they may have never even considered themselves. It can be as simple as “If you were a baseball player, what would your walk-up song be?” to “If you had one free day to do whatever you wanted, how would it start?” to “Which movie character would you want to be stranded on a deserted island with?” to “What’s the best compliment you’ve ever gotten?” to “If you could create a new Crayola crayon – what color would it be and what would you call it?”

Sometimes deep and introspective, sometimes random and silly — the full spectrum of what it is to be human.


This inquisitive intentionality has trickled over to my work at helping open my family restaurant, Slicker’s Eatery. The last question in every interview we gave was, “What is a cause you care about?” so we could get some better insight into the heart of the people behind the resumes and applications. One of the first things I did in the building stages was, putting a dry erase board up in the bar that says “Question of the Day”. It was a way for our tight-knit team to get to know each other better along the process and offer some levity in the very long work days. Now, it’s become something that our regulars specifically look for. Next time you visit, I encourage you to ask one of our team members what the Question of the Day is and discuss.

Life isn’t black or white, right or wrong, yes or no. Our humanity is found somewhere in the mix of the messy, beautiful gray. You never get to truly know someone in a binary perspective of Yes or No questions or canned responses to the usual questions. It’s not to get information, it’s to gain insight. It’s about connecting, not checking off boxes. So, I’ll start: If you could have a dinner party with 5 famous people, who would you choose?

Photos from & Molly Slicker

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