Sunday Email: Connecting Thru Questions / Present in Conversation

Read time: ~6.30 minutes

Happy Sunday!

Every Sunday I offer strategies for the week ahead and a thought to fuel your action.

To be curious means having more questions than answers—and discovering that each answer only leads to more questions.

So, is the goal of life clarity or deeper curiosity?

When we travel to new places, we gain fresh perspectives. We're present, taking in new sights, sounds, smells, and tastes. Exploration becomes our way of quenching curiosity. We wander down unfamiliar streets, try new restaurants, and visit landmarks that expand our understanding.

This act of exploration creates intrigue. It brings us perspectives we never had before.

In relationships, curiosity works the same way. Relationships are personal adventures, and conversations are the tools we use to explore them. At the core of every meaningful conversation lies a question. Like an adventure, the right question opens new paths to understanding.

The Decline of Curiosity in Conversations

Over the past few decades, society seems to have shifted. Instead of valuing curiosity, we've started prioritizing answers. Technology, instant access to information, and the speed of communication have created a culture that views questions as a weakness, a sign of unpreparedness or lack of knowledge.

But before the internet, questions were essential. They were the only way forward, the bridge to deeper relationships and connections. People asked to understand, not to prove. And in that slower-paced world, relationships felt more connected.

Why does it seem that more information has brought us less connection? Could it be because we've lost the art of asking meaningful questions?

From Facts to Feelings

The art of a great question isn't about facts; it's about feelings.

Consider common questions like, "Where do you live?" or "Are you married?" The answers are factual but don't tell much about the person. A simple "Yes, I'm married" offers little insight into who someone is.

Now imagine shifting those questions to uncover feelings: "What do you love about where you live?" or "Tell me about your family." These questions go beyond surface-level facts and invite more profound stories, emotions, and connections.

Facts tell us what is; feelings show us why it matters. Knowing a tree is green might be interesting. But finding shade under its branches? That's meaningful.

The Role of Permission in Conversations

Asking questions is important—but how we ask them matters even more. Exploring someone's beliefs without permission is like trespassing on their property. It feels invasive.

When we assume someone understands our intentions or that our questions won't offend, we risk creating distance instead of connection. What if, instead, we asked for permission? "Can I ask you more about that?" or "Would you mind if I explored that idea with you?" These small acts of respect create safety and invite openness.

Age often dulls our instinct to ask permission, but it shouldn't. Connection thrives on trust, and trust begins with respect.

Listening Beyond Words

Listening isn't just hearing words; it's understanding what's behind them. And that requires more than ears—it requires presence.

Words pass through the filters of our unique experiences, which can lead to misunderstanding. To bridge that gap, repeat what you've heard in your own words. This simple act clarifies meaning and ensures alignment.

Pauses are powerful, too. Saying "umm" or letting silence linger gives the speaker space to think and express themselves more deeply.

Imagine two scenarios: driving a race car versus sailing a boat. In the first, every action is reactive, rushed. In the second, there's time for reflection and adjustment. Conversations that connect are more like sailing than driving—they require patience, presence, and flow.

Connection Through Curiosity

To see a tree's strength, you must dig below the surface. The same is true for understanding others. Our shovel in these moments is a thoughtful, relevant question.

We make a mistake when we assume we understand others. Even if the statement seems simple or obvious, there's always more beneath the surface. Stating what we've heard and following up with a clarifying question deepens the connection.

Curiosity isn't just about asking questions—it's about understanding the answers. Understanding begins when we approach conversations as opportunities for discovery, not exchanges of information.

Life Is a Circle, Not a Straight Line

Life is cyclical: we're born, grow, and raise others, only to care for those who raised us. Each stage brings new opportunities to explore and connect.

So, what's the beginning of that connection? What's the first step toward building a meaningful relationship?

A thoughtful, vulnerable question.

A Thought To Ponder This Week

The goal of all conversation is to create connection.

If we create connection we create mutual benefit in conversation.

The act of conversing is simple. Yet the act of conversing to connect remains very challenging.

We take the conversing part for granted.

But we must remain vigilant to ensure that each conversation creates the appropriate connection.

Some connections with be more emotional, others will be more tactical.

Either way, connecting appropriately ensures the conversations delivers effectively for both parties.

In order to continue to improve our conversing ability, we must continue to be self aware.

Aware of the tone, the needs and the desires of a conversation.

As you enter your next conversation, try to be more present and identify the cues and be sure to know what it is you want out of the conversation. This may make for an unexpected connection.

The best is ahead!

-Matt