Questions We Fail To Ask

I’m not entirely sure where I’m going with this, but that’s kind of the point—figuring things out by asking questions.

Lately, I’ve been thinking a lot about how questions shape our relationships, careers, our choices, and even our relevance in the workplace. You know those people in meetings who always seem to have a question for everything? The ones who aren’t afraid to raise their hand and ask the VP why they made a particular decision? Yeah, those people. They get noticed.

And it’s not just about looking smart. It’s a signal—one that management pays attention to. Because the people who ask questions aren’t just following orders; they’re thinking, engaging, and challenging the status quo. That’s a different playing field altogether.

Wait, Aren’t Questions Annoying?

Let’s be real—we weren’t raised to ask questions.

If you grew up like I did, asking too many questions meant you were difficult or rebellious. There was a fine line between being “curious” and being “disrespectful.” You obeyed. You nodded. You didn’t question authority.

To this day, I still hesitate before calling people older than me by their first names—unless we’re friends. Even then, it’s always something like “Boss” (just to be safe, hahaha).

And yet, we were somehow expected to grow up and become leaders? How does that even make sense? Leadership isn’t about blindly following orders—it’s about making decisions. And making decisions? That starts with asking the right questions.

For the longest time, I didn’t ask enough questions. Sure, I asked the obvious ones, but not the real, uncomfortable, game-changing ones.

You know that moment in a meeting when someone presents an idea, then asks, “Any questions?" And everyone just sits there, nodding, pretending they understand? Yeah, I used to be that person.

Not because I understood. I just didn’t want to look stupid.

And then—plot twist—I’d leave the meeting totally lost, only to realize everyone else was just as confused as I was.

Hahaha. Classic.

But here’s the thing: If no one asks, no one learns. And if you don’t learn, you don’t grow.

So about two years ago, something clicked. I started asking more questions—not just at work, but in life. Why are we doing this project now? Why is this task a priority? What does that acronym even mean? (Seriously, why do people throw around acronyms like we all signed the same secret contract?)

And something amazing happened. I felt more informed. More aware. More relevant.

Not All Questions Are Created Equal.

Let’s be honest—not all questions are good questions.

There’s a difference between asking a question to learn and asking a question to flex. We’ve all seen that one person in a meeting asking questions just to sound smart. (Spoiler: It never works.)

But when you ask the right questions—the ones that seek clarity, challenge assumptions, or spark new ideas—you level up.

Imagine if everyone asked better questions. The right ones. The hard ones. The ones that get to the root of things.

There’s actually a framework for this called the “5 Whys” method. (I don’t practice it much—maybe when I’m an exec, I will—but the idea is cool.) The concept? Ask “Why?” five times, and by the fifth, you’ll hit the real problem.

Example:

1. Why is this project delayed? → Because we’re waiting on approvals.
2. Why are we waiting on approvals? → Because the VP is busy.
3. Why is the VP busy? → Because they’re swamped with too many decisions.
4. Why are they making all the decisions? → Because the team isn’t empowered.
5. Why isn’t the team empowered? → Because we don’t have clear ownership.

Boom. Now we’re talking about real solutions.

You know who asks the best questions? Kids.

They don’t care about looking dumb. They don’t hesitate. They just ask. And because they ask, they understand the world with more clarity (and a lot more fun). Atleast, before they stopped asking questions. Or we Adult prevent them from stop asking questions.

Somewhere along the way, we stop doing that. But what if we didn’t?

What if we questioned things more? Our jobs, our choices, our assumptions?

What if instead of blindly following, we asked: Why?

And more importantly—what could change if we did?

Disclaimer: I don’t think I like when people ask me too many questions, weird!