The Underrated Superpower: Asking Better Questions

Ever catch yourself in a conversation where you're just waiting for your turn to talk? You nod along, maybe throw in a “yeah, totally,” but really, your brain is working overtime crafting that perfect response—the one that makes you sound insightful, witty, or just plain smart.

We've all been there.

But while you’re busy planning your next mic-drop moment, you might be missing something big—an opportunity to learn, connect, and actually get to the heart of what matters.

Asking the right questions isn't just a communication trick, it’s a superpower. It builds trust, uncovers hidden truths, and transforms relationships, businesses, and even entire industries.

Why Questions Matter More Than Answers

Here’s a fun fact: the most successful people aren’t the ones with all the answers. They’re the ones asking the best questions.

Take a look at the world’s top investors, founders, and innovators—they’re not just throwing out bold statements. They’re relentlessly curious. Jeff Bezos built Amazon by constantly asking, "What won’t change in the next 10 years?" Elon Musk rethinks industries by asking, “What are we assuming to be true that might not be?”

Even Einstein credited his success not to intelligence, but to curiosity. He said, “I have no special talents. I am only passionately curious.” The guy revolutionized physics, not by memorizing formulas, but by asking simple yet profound questions like, “What if I could ride a beam of light?”

In business, leadership, and life, better questions lead to better outcomes. Period.

The Cost of NOT Asking Questions

Let’s look at the other side for a second. What happens when you don’t ask questions?

Imagine a leadership meeting where everyone is more focused on pushing their own agenda rather than digging into what’s actually going on. Creativity flatlines. Innovation stalls. Decision-making disappears.

Or think about a relationship where no one asks how the other person really feels. Over time, emotional distance creeps in, and what was once a deep connection turns into a series of surface-level interactions.

The truth is, a lack of meaningful questions doesn’t just lead to boring conversations. It leads to missed opportunities, weak relationships, and businesses that plateau instead of scaling.

Why We Suck at Asking Great Questions

It's not like we’re trying to be bad at this. We’re just wired to prioritize answers over curiosity.

When we were young, we got rewarded for getting the right answer and for not for asking why things work the way they do (aka: insubordination). Schools hand out gold stars for memorization, not curiosity. In a lot of businesses, assertiveness is valued over open-ended thinking. But sometimes the culprit sits within each of us. 

• We assume we already know the answer. (Spoiler: We don’t.)

• We’re impatient. We’d rather share our perspective than wait for someone else’s.

• We’re afraid of looking uninformed. But real confidence comes from curiosity, not certainty.

So, how do we move from surface-level small talk to game-changing conversations? Master the art of listening. 

Before you can ask great questions, you need to actually listen. Really listen.

Not the kind of listening where you're just waiting for a pause so you can jump in. Not the kind where you're half-distracted by your phone or mentally rehearsing what you’re about to say next. Real listening is active. It’s about tuning into what’s not being said just as much as what is being said.

Pay attention to:

• Tone – Are they excited? Frustrated? Hesitant?

• Pacing – Are they speaking fast, like they’re eager to get something out, or slow and measured?

• Pauses – Sometimes, what someone doesn’t say speaks volumes.

When you listen on this level, you’re no longer just exchanging words—you’re engaging with emotions, ideas, and perspectives. And that sets the stage for asking the right questions.

So how can you level up your questions?

1. Go Beyond the Basics: Instead of asking, “How was your day?” try, “What was the most challenging part of your day?”  One invites a generic response. The other invites insight.

2. Use Open-Ended Questions: Yes/no questions kill conversation. Instead of “Did you like it?” try, “What stood out to you?”

3. Follow Up: One great question deserves another. If someone says something intriguing, dig deeper. “That’s interesting—what makes you say that?” or “Tell me more.”

4. Make It About Them: Resist the urge to immediately jump in with advice. Instead of saying, “You should try…” ask, “What have you considered doing next?”

You’d be amazed what people will share when you give them the chance. 

The quality of your life, leadership, and relationships are directly tied to the quality of your questions. The right questions can unlock ideas, challenge assumptions, and create deeper human connections.

So next time you find yourself zoning out in a conversation, waiting for your turn to shine, stop yourself.

Listen.

And then, ask a question that actually matters.

Here’s a question for you: 

What’s one question you should be asking more often but aren’t?