Ask Better Questions, Make Better Connections

Whether it’s hanging out in the barn with the horses, or my professional work as a branding expert, my life’s work revolves around depth and connection.

I don’t do surface, I don’t do quick fixes, and you might even remember when I wrote about how I don’t do the ever-popular weekend branding intensives.

If I’ve learned one thing, it’s this:
You won’t get to a deeper place of connection and you won’t delve into an abundance of possibilities in conversation if you’re asking basic questions.

As simple as it sounds, you’ve got to ask some interesting questions, actively listen to the person speaking, and be willing to dive in deep yourself if you want the quality of your conversations to increase.

Boring questions lead to boring answers.
And I think we can all agree that “so, what do you do?” sends us each into a yawn.

And even worse than coming off as boring? Asking lackluster questions invites non-specific responses. The more general and vague we are in our statements, the more room there is in the conversation for projection and guesswork. (Which is why knowing the core pillars of your brand message is so important and a big part of what I do in my work, but I digress!)

What’s so bad about asking a question that prompts a vague answer? It thwarts connection.

When I lived in NYC in the late 1990s, the incorrect answer to the question “so where do you live?” was enough to abruptly end a conversation.

Why?

Because our brains are wired to attach meaning and make assumptions based on very little information – and a zip code carries no context, no heart and soul, no deeper explanation of what message we’re wanting to get across.

So how do we take our conversations to a deeper level?

How do we ask questions that bring our values to life?

1. Get some ideas ahead of time.

I’m a fan of Rob Walker’s work (and not just because I met him when I was living in Savannah), and his Icebreakers Google doc has become quite the resource for everyone wanting to have more interesting conversations.

2. Practice with the people closest to you.

Next time you’re in a conversation with a partner, friend or a colleague and there’s an opening to move past, “hey, how was your weekend?” try an interesting question or icebreaker to learn a bit more about them (and invite them to do the same)!

3. Be willing to step out of your comfort zone.

We get in question-asking ruts because it’s comfortable, not because it serves our deeper desire for connection. The first few times you try it might feel a little awkward, but that goes away with practice.

So go ahead and try it out!

Send me a note to practice one of the icebreaker questions from Rob Walker’s google doc, and get ready for me to ask you one in return.

Talk soon!
Jocelyn