Sunday Email: Listening

Read time: ~4.00 minutes

Happy Sunday!

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

Discussing difficult topics can feel less like a conversation and more like a battle of wits. It’s as if we’re preparing for a debate rather than a simple exchange of ideas.

Instead of just talking, we strategize. We collect our information, decide how to use it, and plan our points to ensure we “win” the conversation. Sometimes, it feels more like planning a covert operation than just speaking our minds.

Why is it so hard to just talk these days? We either strengthen our shared beliefs with those who already agree with us, or we argue, trying to convince others of our way of seeing things.

Our struggle with difficult conversations—whether about politics, values, or social issues—has less to do with our actual beliefs and more to do with the mindsets we bring to the table.

Take political season, for example. Tensions rise, and people seem primed to take sides. Imagine I began a post with either “I support Kamala Harris” or “I support Donald Trump.” Suddenly, the rest of my words would change shape for the reader.

Those who agree with my stance would nod along, perhaps unconsciously finding my words insightful, even “proof” of what they already believed. And those who disagree? They’d likely argue every line in their minds, building a counterargument as they read. For one side, I’d be wise; for the other, misguided. Same words, same ideas, yet two completely different interpretations.

Curiosity fades when our instinct is to take sides. Instead of exploring where we might find common ground, we fall back on “us” versus “them.” Rather than listening, we’re preparing to be correct.

Our natural human need for acceptance drives us to convince others, not to connect. As social beings, we’re wired to be part of groups, whether supporting a sports team, backing a candidate, or standing for a cause. Belonging has always meant safety—a necessity for survival. Our ancestors knew the risks of being alone, and while society has evolved, our instincts haven’t entirely caught up.

Imagine two people looking at the same tree. One sees vibrant fall colors, and the other sees sturdy branches. They’re both right, yet they might debate each other, laughing off their “silly” differences, never once stopping to ask, “Tell me more about why you see it that way.”

Those three words—“Tell me more”—slip from our minds as we rush to persuade, to bring others over to our side. It’s as if the drive to feel understood outweighs the desire to understand.

Assumptions are our own cheat codes to help us advance levels in our game of life, but they come at a cost: they blind us to empathy.

Think about the last time you asked someone, “How are you?” What did you do with their answer? Did you accept it at face value and move on, or did you dig deeper? When someone says they’re “good,” we assume we know what they mean. Of course, we all know what “good” means, so we assume that their “good” is the same as our “good” because “good” is “good” and we are all “good” with that. It’s a simple, convenient cheat code. But is it understanding, or are we just moving on?

Difficult conversations aren’t about reaching a consensus. They’re not about thinking alike. And they’re not a tactical game requiring strategy and rehearsed arguments.

Instead, maybe the only tool we need is self-awareness. Curiosity makes it easier to explore something we don’t know than to defend what we think we do. When curiosity guides us, our conversations lose the friction that often builds around difficult topics.

Imagine a conversation where, instead of proving a point, we’re genuinely interested in learning something new. What could change if “Tell me more” became our default response?

A Thought To Ponder This Week

Are you listening?

Yes.

Are you really listening?

Likely no.

Despite living in the present moment, we tend to find our minds in other moments.

The past, the future, the what ifs, the what could be.

And so, yes we are listening. We hear the words. We understand the words. Yet, we don’t comprehend what the words mean together.

The idea of being present and actively listening goes beyond being in the same spot as the other person and hearing what they have to say.

Active listening is more like being the batter in a game as opposed to the spectator. The spectator is there and understands what is going on, but not highly engaged and neurally synced with the moment in the game.

Despite not being a professional athlete, we are constantly at the plate in every conversation.

It’s our choice as to whether we are the batter or the spectator.

So, as you enter your next conversation with a team member or a client, I urge you to become more aware… are you the batter or the spectator?

The best is ahead!

-Matt