Try Asking People Why Things Matter to Them

It can make your conversations weirder and more interesting

Before I get into this, caveat. You shouldn’t ask this question in all circumstances. Many—most—conversations don’t provide the right context. Its use requires judgement. Don’t blame me if you end up with awkward results after you throw this question around indiscriminately in an attempt to be some kind of Social Hacker or amateur cult leader. Not my fault.

But it can be a genuinely great tool. To paraphrase Kafka, it can serve as an axe to shatter the frozen seas of idle conversation.

The question is: “why is that important to you?” 

I’ll talk about the practice of this question first, then the theory. 

(Also, credit where credit is due. I learned of this question through Misha Glouberman, who you should hire if you need a negotiations expert/facilitator—he discusses the question in the context of negotiation, which is related but different.)

Recently I was drowning in a conversation at a wedding. I was talking to a very kind, smart person about her academic work, which I was struggling to maintain interest in, through no fault of hers. Though I’d like to be the kind of person who can eagerly suck up a bunch of facts about European history after a couple of glasses of Prosecco, I am not. 

I knew she was cool and interesting, but I was finding myself increasingly irritated and lost. But before my meager attentional abilities failed completely, I remembered my handy question: why is East Germany important to you?

There was a pause. Her face changed. You could almost see her reaching down into a different floor of the inner library. And then she explained: her parents were from East Germany. She’d never had much of a relationship with them, and the country no longer exists. As a result, she’d always felt rootless in the world, bereft of a home, or even a sense of home. Through her academic research, she could create an intellectual/emotional home for herself.

Our interaction was transformed. Suddenly, I cared about East Germany in a way I hadn’t expected to. And I think she felt understood in a way she hadn’t expected to. And I could tell her, too, about all sorts of ways I felt rootless and alienated in the world. Asking one question at the right moment turned a passable conversation into a memorably good one. It was a magical portal into a different social plane.

Most activities we participate in are charged with some sort of meaning. Nearly everything we do is connected to some deep layer of our identity or history. Even frittering away our evenings on YouTube—perhaps we’re engaging in avoidance behavior because we want to assure our own failure. Or perhaps our work has become more emotionally demanding recently, and dissociating has become a necessary element of our self-maintenance routine.

This deeper stuff is often way more interesting than the surface behavior. If you hear that someone is gaining muscle mass, that’s kind of cool. If you hear that someone is gaining muscle mass as a way of embodying their attempt to take up more space in the world after a lonely, trauma-filled early life, that’s obviously a richer subject of discussion.

But our deeper strata are totally opaque to most people we’re speaking to. And, also, funnily enough, they’re often opaque to us. Our values and history are the vessels that shape our behavior, but they’re often transparent in the moment. Few of us step back regularly to examine why we’re living our lives this way. And even if we do, the rigors of daily life require us to move that stuff into the cognitive background to get things done.

Accordingly, when someone tells you that they’re excited that their new job will pay them more money, and you ask why that’s important, you’re inviting them to engage with themselves more deeply, as well as you. Why is money so important in their particular case? What do they need the freedom to do? Do they have a passion for fine wine that needs indulging? If debt is their motivation, what violence did they do with their credit? 

In the best-case scenario, if you ask someone this question, you’re both giving that person the space to understand themselves aloud, and the opportunity to connect to you more deeply.

It’s delicate, though, as previously mentioned. Not everyone wants to enter into a vulnerable conversation about their values and intentions. And the question can come off confrontationally if it’s delivered with the wrong tone. (“I’m just curious” is a nice thing to preface the question with.) 

However, a lot of people do want to be seen. And before they can be seen, they need an invitation. And this is one powerful way to extend that invitation, instantaneously. Try it. You might find yourself having unexpectedly rich, charged interactions with all sorts of people in your life.

But, first, I’m just curious—why is that important to you?