Tuesday Email: The Art of a Question

Read time: ~4.30 minutes

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

A question opens doors; a statement closes them.

Have you ever been in a conversation where, at the end, you realize you’ve been talking the whole time?

I’ve been there. And despite the guilt of owning the conversation, I felt great.

Because we all yearn to be heard—it’s a form of acceptance. That’s why asking questions creates connection, while statements often fall flat.

A question gives someone the space to explore their thoughts aloud. And in that exploration, something incredible happens—walls come down, vulnerability rises, and authentic connection forms.

Five years ago, I sat in front of my mic, mid-recording, realizing something felt… off.

I was talking, sharing, explaining. But when I hit stop and listened back, I noticed something obvious to others: It was just me.

I had no guests; I wasn’t learning. I was just filling space.

That’s when it clicked. The best podcasts weren’t platforms for hosts to talk. They were masterclasses disguised as conversations.

Hosts weren’t lecturers—they were explorers. They asked, they listened, they learned.

So, I changed everything.

I started interviewing people—technology leaders, marketers, wealth managers—giving them space to talk while I listened.

But what I found most satisfying wasn’t just the conversations themselves—it was crafting the questions and then scrapping them when the moment demanded it.

Because the best questions are not the ones we plan—they’re the ones we discover in the moment.

I used to think a well-crafted statement was the most powerful way to communicate.

I was wrong.

Questions go deep. They ignite authenticity and bring out truths that a prepared statement never could.

If you want people to remember something, a question is more powerful than a statement.

A statement is passive. A question is active.

A statement is information. A question is engagement.

A statement is giving an answer. A question is creating a connection.

Think about learning to drive:

You can hear someone explain how to drive for hours. But until you actually get behind the wheel, you don’t learn.

A statement is like telling someone how to drive.

A question is putting them in the driver’s seat.

Yet somewhere along the way, we stop asking questions—not because we lose curiosity but because we are trained out of it.

Children are born explorers.

Before kindergarten, they ask countless questions.

But the moment structured education begins, curiosity shifts from exploration to performance.

“What’s the answer?” replaces “What if?”

“What’s right?” replaces “What’s possible?”

We become trained to be right rather than curious to be better.

As in all things in life, there are negatives to something so positive. And for questions that lies in asking “why.”

Think about the last time someone asked you why.

Did you feel open and reflective? Or did you feel the urge to defend?

“Why” puts people on the defensive.

It’s like a stop sign—it forces a pause, a justification, and often, an exit.

If you genuinely want to understand someone, replace “why” with “what” or “how.”

Instead of “Why did you do that?” → Ask, “What led you to that choice?”

Instead of “Why do you believe that?” → Ask, “How did you come to that belief?”

One puts up walls. The other opens doors.

Too many doors are slammed shut because of differing views.

And we keep kicking them shut—using statements to convince others that we’re right and they’re wrong.

But maybe we’re using the wrong tool.

Maybe the answer isn’t in statements that close conversations.

Maybe the answer is in a single, well-placed question that opens one.

The best is ahead!

-Matt