The holiday season is upon us, meaning chances are good you may have more family and social get-togethers coming up. But whether you dread holiday parties and figuring out what to chat about with everyone from young to old, left or right, happy or sad, and everything in between, or you just want to have more fulfilling interactions with those you cross paths with, Charles Duhigg, author of the bestseller, Supercommunicators, has some advice for you: go deep. Not deep philosophical but deep with the kinds of questions that give you better insight into who those around you really are. And not deeply personal questions that feel weird and intrusive (“What don’t you like about yourself?”) or go from 0 to 60 in intimacy right after “Nice to meet you.” Just questions that take a standard topic –“Where do you live?” — one step further by asking, “What’s the best part about living there?”

What this kind follow-up question does is get at how they feel about where they live. When you get beneath the factual surface into the feeling then you’re moving into something interesting, revealing, and multi-dimensional about this person. Scratching below the surface in this way also often spins off into a dynamic conversation about what you happen to love and hate about where you live and so on and so forth. Before you know it, the two of you have figured out you both have an hour commute to work and are trading tips on making that work. 

Another good question that gets at personal experience is, “What’s that like for you?” It can be applied to practically anything:

• “What’s being the CEO of a big company like?”
• “What’s having four kids under age five like?”
• “What’s working the night shift like?”
• “What’s mentoring high school students like?”
• “What’s going back to school at age 50 like?”
• “What’s living in a different state than your spouse like?”

It’s so fun to make up those questions I could go on and on except now I really want to know! (I get some of those questions answered in the What’s it Like To Be podcast exploring all manner of professions from forensic accountant to rancher, Secret Service agent to ocean lifeguard, NBA referee to long-haul trucker and on and on.)

Another typical small talk question easily made deeper is, “What do you do for work?” You can follow that up with “Do you like it?” and “Is there something else you dream of doing?” and now you’re off to the races.

I know these sorts of tips can be hard to operationalize. To simplify, making a more meaningful connection with someone can come down to a memorizing a few basic questions:

1. What’s the best thing about ….?
2. What’s it’s like to …?
3. Do you like that?

Even asking those questions to people you think you know inside and out will probably turn up something surprising. The bottom line … it feels really good for someone to take an interest in us and when we take an interest in someone else it makes us more likeable. It’s a happy situation for all because we’re wired to connect. What’s more, research now shows that connection is crucially central to health.

We don’t have to make a big project of interviewing everyone we encounter which could come off weird and like we’ve got an agenda to Make Connection Happen. But softly going a little deeper with someone to find out what it’s like to be them and if they like what they’re doing might spark a really satisfying conversation at your next holiday gathering.

Cheers!

E