I can’t tell you how many brilliant humans I coach who, as smart as they are, often play a little duhᐧmbfounded when it comes to having deep and connected conversations — whether it’s with their co-workers, employees, bosses, partners, teens, etc. Let alone with someone they’ve just met and want to get to know!

In these odd (to say the least and the nicest) times, isn’t it about time we bypass the bullshit and go deep, QUICK? I mean, come on: F talking about the weather.

[What?! It could stand for forget, forgo, or forsake!}

Don’t get me wrong, there isn’t one of us – myself, friends, and family included – who couldn’t easily get caught up in a shallow conversation; from what happened at work today, to what do you do, to where do your kids go, to who do you know, and so on.

Truth is, it was actually my two sisters and my fault that we even started curating dinner conversations in the first place. Hard to imagine, I know (cough, cough), but whenever my sisters and sister-like friends get together – no matter when we last spoke, even if it was twenty minutes ago, it’s as if it’s been AGES. Often, much to some of our polite-r, non-interrupting, passive aggressive-r partners’ dismay.

Namely, mine.

For the past several years, Friday night dinners have become a mainstay at my sister Marnie’s house and although everyone, of course, is BEYOND welcomed to join in our “catch up” yack-fest, the men in our group, just sorta watch and, well, watch.

I remember this one time, in particular, when my husband, David, the politest of the lot, half-jokingly, kinda cutely, slightly pathetically, raised his hand to see if he could get a word in. And, voila, in that moment, we adopted the following new party policy:

For the first 20 minutes or so of every gathering, the sisters and friends are free to hungrily “catch up.” However, once we sit down to dinner and everyone gets comfortable, one person, usually my brother-in-law, CEO of HG, and party host, Shir quiets us down (see: he’s Israeli and has substantial military training) and introduces the process of curating a conversation to any newbies at the table. We do this at every dinner, no matter how many people are at the party, from 8 to 48.

And because having connected and curated conversations has been such a game changer for us, I’m sharing them with you. Because if we’re ALL not the ones causing connections, who is?

So, here’s a sampling of some of our favorite curated conversations, ranging from the shallow end of the pool to the deep. Obviously, “swim” at your own pace (only better!) and anything you ask, be prepared to answer. Some are more “out there” than others. But remember, the bolder you are in your life, the more the people in your life will meet you there.

Shallow end:

• Knowing what you know now, if you could swap what you studied, what would you have studied?
• Best high school moment?
• Worst high school moment?
• Have any siblings? Favorite thing about each sibling?
• Favorite teacher/mentor story?
• Freshman roommate story, godsend or god awful?
• What’s on your bucket list? Why?

Knee deep:

• Groundhog Day moment: What moment in time would you go back and do differently, if you could?
• Greatest character trait you got from your dad/mom?
• Worst character trait you got from your dad/mom?
• Everyone has their own brand of magic (ie: thinking of someone and them calling or emailing shortly thereafter) What’s your magic? Give an example.
• What’s a superpower you want? Why?
• What’s something you’re most proud of?  Why?
• Biggest regret?
• Advice you’d go back and give your tween self? Your teenage self? Your twenty-something self? Your thirty-something self? Yesterday?
• Describe a spiritual moment (however you define it) you had in your life?
• [Borrowed from Inside the Actor’s Studio] If heaven exists, what would you like to hear god (or whomever/whatever you believe in) say when you arrive at the pearly gates?
• If you could pick any career in the world, regardless of ability or age or salary, what would it be? Why?

Deep end:

• What’s a fight you had with someone that you’re still reliving, stewing over, and/or waiting for an apology?
• Describe your most embarrassing moment. Any long lasting decisions (good or bad) you made from it?
• What’s a sex story you were, UNTIL NOW, going to the grave with?
• What’s your favorite thing about you?
• What’s one of the biggest lies you ever told that you got away with?
• What’s one of the biggest lies you ever told that you didn’t get away with?
• If you could change one thing about yourself, what would it be? Why?
• What’s something you saw, heard, or experienced this week that moved you?
• Share one CUTE thing about you that no one knows.
• What three things are guaranteed to make you smile?
• Name something you’re scared of but would love to find the guts to do.
• If someone gave you one million dollars and you had one month to spend it, how would you spend it?

You know how the warning label on certain risky things usually reads, “don’t do this at home.” Our recommendation is quite the opposite: do this at home and, while you’re at it, everywhere else, too.

Love,

Lauren

P.S. What’s your life like? Sucky? Sexy? Somewhere in between? Take the Current Reality Quiz! It’s a quick, easy, and fun (we swear) way to self-assess and get a better idea (or at least an honest one) on what areas of your life you need to work on.

Lauren Handel Zander is the Co-Founder and Chairwoman of Handel Group^®, an international corporate consulting and life coaching company. Her coaching methodology, The Handel Method®, is taught in over 35 universities and institutes of learning around the world, including MIT, Stanford Graduate School of Business, NYU, and the New York City Public School System. Lauren is also the author of Maybe It’s You: Cut the Crap, Face Your Fears, Love Your Life (Published by Hachette Book Group, April 2017), a no-nonsense, practical manual that helps readers figure out not just what they want out of life, but how to actually get there. She has spent over 20 years coaching thousands of private and corporate clients, including executives at Vogue, BASF, and AOL. Lauren has been a featured expert in The New York Times, BBC, Forbes, Women’s Health, Dr. Oz, and Marie Claire and she is a regular contributor to Businessweek and the Huffington Post. Click here to schedule a 30-minute consultation with Handel Group.

Image courtesy of Lee Hnetinka.