Your Questions Suck. Here’s What You’re Missing.

Never get feel out of place again. Maybe.

A few weeks ago, I noticed something special.

I noticed that people usually hid the best, most interesting parts of themselves from the rest of the world. Understanding someone meant slowly bringing those things out and appreciating your discoveries. It’s a nice reminder us that we can always care about others — even if they’re nothing like us:

When trying to really understand a person, you’ll realize just how valuable asking the right questions are.

Not only does it help you go further than just talking about the work or the weather, but it’ll open up doors you never knew existed. Questions are what got me my first paycheck, my best friends, and a full-ride through university (I’ll talk about that later) — but those things come second to all the little, curious things I learn about people all the time.

Yeah, questions can do that — you just need to know how to ask them. And hey, it’s about time we learn.

1: Don’t Inflate Your Words.

If you think back to high-school business class, the more money a country prints, the less valuable its currency gets. Money loses its value when there’s more of it to go around. That’s inflation.

Words work in a similar way. The sheer volume of what you say doesn’t matter nearly as much as the value it provides. Don’t ask just for the sake of it. There’s a good chance you’ll end up saying things you don’t even believe in, and then cringing every time you think back to that talk.

Instead, talk when you think you really have something to say. Train yourself to the point where everything you say has at least some intention behind it. Without purpose to fill your words, they’re going to be empty and worthless. Train yourself to the point where everything you say has at least some purpose behind it:

“Stop yourself from saying things that you wouldn’t want to be asked or told. It’s fine if you speak less than usual, as long as there’s more value saturated in the few words you do say. When you do that, better questions come without much extra effort.”

What does this all mean? To explain things a bit better, I’ll give you a story I almost convinced myself to cut out of this article.

Back when I was in grade five (or is it fifth grade?), I lived too far from my school to walk there. So, to get to school, I walked over to the bus stop that was right next to the apartment building I lived in. On the average day, about four or five other kids (mostly my friends) waited at the same place:

And I kid you not — basically every single day was pure silence. We knew each other pretty well, but like I said earlier, there wasn’t to talk about.

I absolutely hated it. It felt like we stuck in a cramped elevator, but for for half an hour — every single day. That’s why I tried saying to try getting everyone in a conversation and clearing up the atmosphere. Why’d it have to be me, of all people? No idea. I guess I was just that kind of person.

And what’d I expect?

About ninety percent of everything I wish I didn’t say in my entire life happened at that bus stop. Some notable fails include me assuming someone was pregnant when they really weren’t pregnant, or even a woman. Just take a moment to think about the mental pain I went through.

Soon enough, nobody at my bus stop ended up taking me seriously. They saw that the words I said didn’t mean much, and slowly grew distant. Of course, everything was fine in school since we everyone wanted to talk there. But let me tell you — that bus stop was the real-life version of “A Quiet Place”.

I’m not scared of monsters or ghosts or even the dark furnace room in my basement. They mean nothing to me. But I swear — those incidents happened years ago, and I still have nightmares about them:

“At the time, I didn’t know that saying something didn’t necessarily mean I had something to say. Don’t make the same mistake I did.”

Before you ask a question, ask yourself: “Why am I asking this? What is it going to do? How is it going to help me or the people around me?” It’s hard to go wrong if you have a reason.

2: Go With The Flow.

Ever notice the difference between a scripted interview and the ones where both people totally wing it? The first option always gives you nice, clean questions and answers, but not much more than that. The second one’s usually a bit more risky, but when it works, it really works.

Like I said earlier, good conversations can get the best out of people, and they can make you laugh and think and learn all at once. You’ve probably had an interaction like that, but it might’ve been rare:

To make more of that magic happen (without relying on you accidentally “clicking” with someone), it helps to think about why those unscripted interviews hit it off, while the inorganic ones just don’t give you the same feeling.

The answer’s spontaneity.

When something’s scripted, there’s enough room for talking, but not enough for an actual conversation. Both people know how and when they’ll ask or respond, but that’s never an environment where either person can be genuine. Why’s that? Because no matter how you answer, you know the next question’s always isn’t going to change:

“The conversations that really matter are the ones that evolve and have the freedom to stray from the intended path.”

Both people should feel like they have the ability to influence what’s going to be said. When the topics and things you talk about get too constrained, conversations turn into interviews — and we all know that nobody enjoys interviews.

Here’s what I mean:

Fast-forward from my middle-school life to the pandemic, and anyone who likes social interactions is getting burned at the stake. Let me give you glimpse of how I was holding up through all this:

At my lowest point, I realized that basically every video call I had went something like: “How’s it going?”, and then “Oh, that’s cool (I really didn’t think what they said was cool), and then “Alright, cya”.

For lack of a better way to describe it, it was bad.

I had to learn the value of loosening up and not worrying about the outcome the hard way. But now, when I put spontaneity first, it doesn’t matter if it’s a video call or a suspiciously-worded text — I know I can make things work.

Before you ask a question, ask yourself: “Would I have asked this question anyway — regardless of what the person I’m talking to said?”. Catch yourself when you start sounding like an email template or a greeting card. Throw away your internal script every once in a while. Do that, and you’re always in for a fun time.

3: Rely on Others.

But, as useful as all these rules can be, they’re just nice-to-haves if you can’t get a conversation started in the first place.

What do I mean? Something like this:

You could think of the most spontaneous, intentional way to start a conversation with the person who sits next to you at work. That great!

But (and this is a very important but), if you end up asking them where the coffee machine is or what their name is, you’ve basically signed a contract to stay their acquaintance for the rest of your life.

Why? Because anyone could’ve answered that.

I call questions like those “non-questions”. They’re things you could figure out yourself, or if you just asked around.

The last time I was on a flight (headed towards a city in Eastern Canada), I tried having a conversation with the stranger sitting next to me. And as a **great** thought-starter I asked him:

“So, you’re flying to Fredericton?”

Seriously, I want to punch myself in the face for saying that. I mean, come on — it was a one-stop trip going to one destination. It’s not like he was going to jump off the plane halfway.

I don’t exactly remember how he responded, but I’m pretty sure he pretended not to listen. When someone does that, you know you messed up.

Now, that’s how you don’t start a conversation. To prevent certain doom, take some time to think about how you can find something unique to ask them.

That almost always means going away from the beloved structures of “Who”, “What”, “When”. “Where”, “Why”, and “How”. That’s the anatomy of an average question. Most questions are usually so bland that when you throw something new into the mix, people take notice:

Ask “if” questions to make people imagine about a completely different future. Ask about “would” or “could” to make people reflect on their lives. Really, it’s hard to overdo it.

I’m talking about “Would you change anything about your life?” or “If you could meet yourself from ten years ago, what would you tell yourself?”.

No one else can answer those questions for them. That’s the power of asking about things unconventionally.

Just realize that this isn’t one of the ten commandments. It’s a rule-of-thumb designed to get you to to ask better, more exclusive questions. Override it as much as you want, as long as it serves its original purpose.

For example, asking someone how they’re doing is much deeper than asking them what they’re doing. Again, it’s all because only that person can answer the first question, while any fool who follows that person on social media can answer the second. You get the idea.

Before you ask a question, ask yourself: “Could someone else (or even Google) answer the question I’m going to ask this person?” If yes, think of something else designed just for them. Make every question with someone in mind, and they’ll always see it as a gift.

4: Don’t Overthink It.

Oh, and one last thing. Even if you know what you’re going to say is important and valuable and spontaneous and everything in between, you might hesitate. Even if it’s for a second, you’ll second guess yourself.

Right before you put your question out there, ask yourself if you’ve done your best to make it a good question. And if you’ve followed everything up till now, trust me — you’ll be fine. Now go. Make something wonderful happen.

Thanks for reading,
— Aaryan (Your best online friend)

I write about things every week(ish).

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