How to Have More Meaningful Conversations

I grab a seat at the corner of a large rectangular table. The centerpiece is a mason jar of pencils and an old school pencil sharpener. The table is made of reclaimed wood set on top of antique school lockers. In some ways, the school theme is the perfect setting for a morning of conversation and companionship.

I wasn’t alone at the table. Seated on stools around the table were 10 of the people I most enjoy spending time with in Atlanta. We were getting together for the first monthly breakfast club. A no-agenda gathering for a group of people interested in having good conversation and forming strong bonds with other good people in our city.

Breakfast club is one of the of ways I try my hardest to create or join settings where deep conversation is not only acceptable, but encouraged.

Let’s be honest, deep conversations about the things that actually matter — relationships, faith, money, careers, struggles, opportunities, or maybe even big ideas about the future — are taboo in the average social setting. If you show up to a typical networking event and ask a probing question, you better be ready for some form of stank face in return.

Somewhere along the way, we lost our propensity for meaningful conversation. Maybe it was the culture of stoicism necessary to guide society through times of war in 1914 – 1918 or 1939 – 1945. Maybe it’s the individualistic nature of a purely capitalist or consumerist western society. Maybe it was the Internet. Maybe it was social media.

It doesn’t really matter what caused it. Two simple facts remain: first, we’ve become woefully lacking in space for deep, meaningful conversations with people we care about. And second, going against that trend takes courage, confidence, and risk.

I try my best to create these spaces for the people I care about. It’s something I have to be intentional about because it’s not natural or safe. And it’s something I’ve been encouraged to share my thoughts about.

So here we go… let’s talk about creating space for deep conversations in today’s world.

Safety

Fear is an enemy of openness. Fear prevents us from being open to vulnerability. Fear prevents us from connecting in a genuine way.

We’re trained to respond to fear. It’s a natural human condition. We experience a twinge of anxiety, a heightened awareness when something feels threatening. We run from it.

Marketers and media fuel our sense of fear. Inadequacy marketing reminds us of how lacking we are without a [insert brand name here] in our lives. The morning news reports on the latest apartment fire, the fatal crash, and the impending snow storm.

Fear causes us to seek out easy sources of comfort. Those cheap sources of comfort rarely last. Like a drug, they are a temporary solution for a deeper problem that only create a deeper urge once the high has passed.

The opposite of fear is an openness to possibility. A realistic optimism about the future. A belief that we are capable of shaping our own future and reaching our potential. A belief that we can grow into our hopes and dreams for the future.

We develop that openness through the exploration of new ideas. Of new possibility. Of areas of knowledge previously unknown. Through vulnerability. Through conversation.

That vulnerability can only happen in a setting where we believe we are safe. Where we are amongst peers. Where titles, stature, and wealth are replaced by our humanity, creativity, and desire for connection.

Creating that safety starts with the space and the rules we agree to in that space.

The Rules

The rules. They’re so important. And yet, you can’t just post some rules on the wall or lay a sheet of paper on the table. These aren’t those kind of rules.

The rules are simple.

What’s shared is sacred. It’s for the group, not for outside communities. It’s not information to be broadcast, it’s information to be internalized and carefully considered. “Off the record,” if you will.

Questions are the currency of the conversation. As the cliché goes, be interested rather than trying to be interesting. Deep conversations are born from good questions. We’ll talk more about that in a bit.

Scoffs and gasps are unacceptable. By showing up, you’re agreeing that what’s shared is what matters to the person across the table. Scoffing and eye rolling and annoyance simply leads to people around the table climbing back into their shells.

Posturing serves no one. Puffing your chest and proving your importance are for another time, another place. It’s not useful in this setting. The moment you don your armor, your title, your status, your wealth, the relationship is gone. The intimacy disappears. The hope of having real conversations is lost, at least for today.

A basis of trust. The conversation has to start from a place of trust. Trust in the value of the conversation. Trust in the reaction of the people around the table. Trust in the rules. Trust in each other.

These rules are subtle. They’re almost assumed. This starts with the people you invite. People form cultures. And cultures have rules built in. Your rules come from the people in the room and their shared beliefs.

People

As Seth Godin says, “People like us do things like this.” The people you invite have to believe that they’re the kind of person to show up to a thing like this, at a time like this, in a place like this, with other people like this.

This is whatever you want it to be.

The key is to invite people who can see themselves being a part of a group that has deep conversations together. The Inklings had one meaning of “things like this.” You’ll have another. That’s as it should be.

The most important thing to realize is that the people create the environment. The people in the room set the stage for the conversation. They believe in the rules, or they don’t.

The people don’t have to look the same, but they have to be of the same mindset. They don’t have to have the same religious, political, career, or personal motivations or views. They simply have to be open to discourse.

When you’re inviting the people, remember you’re creating a new normal. You’re creating space to remind people of the power of conversation. The power of vulnerability. It may take time to get there. Which is why building a habit of creating the space is so important.

Habit

Creating a space for deep conversation once is good. It means you’ve taken a risk. You’ve invited people to a table. You’ve asked them to be open to possibility. You’ve asked the question, “Do people like us do things like this? I think so.”

If people don’t show. If they say they’re busy. Or even if everyone shows up… The easy thing to do at that point is to move on. “I tried,” or “I did it,” are natural reactions. But the better reaction is, “That was fun, let’s do it again next week/month.”

The Inklings didn’t have their best ideas in their first meeting. The Hobbit wasn’t born from a single conversation. The Beatles didn’t create their best music in a single session. Trust is not formed in an hour (or three).

Each conversation builds on the last. The habit of conversation is what creates change in people. The repeated exposure to new ideas fuels creativity. The knowledge of the past, the collective conscience grows with each meeting of the minds.

Do it once and I applaud you. Do it every month and you won’t need my applause. The benefit will be apparent.

Creating Space

I’ve said “space” in the abstract repeatedly. So let me give a couple of thoughts on what that means, exactly.

Food

Food always creates a shared experience. It creates natural cadence to the gathering. The in-between moments of silence provide a necessary escape to process any meaningful conversation.

Better than food is good food. Good food creates an emotional experience. It anchors us to a place and time. It is an inherent connection amongst the group.

Perhaps most importantly, food is an excuse. Just enough of an excuse to send that invite. Just enough of an excuse to show up.

“If nothing else, I’ll get some breakfast out of it,” we tell ourselves. “I’ve always wanted to eat dinner there,” we say.

All you need is enough of a reason for people to have the courage to show up. You already took the risk of sending the invitation. Do yourself a favor and make it around food. As you get more comfortable together, the food can come or go. It won’t matter so much.

Today, the day you send your first invite, food is a good excuse to show up. Use it to your advantage.

Introductions

It’s a bit like being a third grade teacher.

“Now, before the food gets here, let’s go around the circle and introduce ourselves,” I say.

Everyone looks at each other with a knowing smirk. It had to be done, but it’s no less hilarious. A group of grown men, sitting around a table with a pencil sharpener in the middle saying a few words about who they are and where they come from.

Without it, they would have left without knowing who they were sitting at the table with. With it, it feels slightly contrived. Slightly forced. Until you (the inviter, the instigator, the impresario) save them from posturing.

People hate introducing themselves. It’s awkward. How much do you share? How humble should you be? How honest about the great work you’re doing? Let’s be honest, it sucks.

So don’t make them decide. Do it for them. Let them say their name and what neighborhood they live in and then take over. Be their introducer. Brag on them. Lavish honest praise on them that comes from a place of knowledge and respect.

“Hey, I’m George. I’m a designer for [XYZ company] I live in Kirkwood,” George says.

You jump in with, “I love George because he says he’s a designer, but really George is a relationship builder. He understands people and he uses his incredible empathy to build things on the web that people will actually use. He’s an incredible father to two awesome kids and a role model of a husband. If that weren’t enough, he runs a meetup for the design community here in Atlanta that’s grown like a weed since it started.”

George is flattered. The group knows who George actually is. And you did the heavy lifting, which is far less awkward for everyone involved. It’s taken as truth instead of posturing. The difference matters. A lot.

Questions

There is a standard bell curve of meaningful conversations. To the left of middle are the negative events in life that we talk about. To the right of middle are the positive events in life that we talk about.

The middle 68.2% is the standard small talk (read: bullshit) we talk about every day. On the negative side are things like the rainy or cold weather, the guy that cut us off in traffic, and the terrible latte the barista made. On the positive side are your new shoes, nice weather, or the extra shot of free espresso.

The 13.6% percent on either side of the middle include, on the negative side, things like you being sick last week or your kid punching another kid at school. On the positive side are the bonus you just got or being pregnant with your second child.

And then there are the harder conversations. The conversations that help us grow. The 4.4% on the very ends of the distribution consist of the conversations we never have, but that we need so badly. The ones that allow for emotional releases and healthy acknowledgement of the true challenges and opportunities we face everyday.

My grandfather is dying of lung cancer. My boss just offered me a massive promotion and I’m terrified I’m not qualified to do the work. My kid is showing a trend of troubling behavior and I’m worried it’s a result of my divorce. I just earned a scholarship to get an MBA at a world-reknowned school, but it would mean I would have to move out of the country and require my spouse to sacrifice her career.

You know, the meat of life. The stuff that actually occupies our mindspace but we tell to go away. The kinds of conversations that “aren’t appropriate” to bring up because it “might offend someone.”

This space we’ve created is for one thing: those 4.4% of conversations you can’t have anywhere else. And the way we get there is with deep, important, daring questions.

Things like:

• What’s the shittiest thing that happened to you this past week? Is it part of a trend or something that happened by chance? How do you feel (gasp!) about that?
• What’s the most exciting opportunity in front of you right now — the one that scares you so much you haven’t even talked about it yet?
• What’s the deepest, darkest secret you’re holding on to right now that’s holding you back from your best work?
• If you could wave a magic wand, where would you be living and working right now? What’s holding you back from making that a reality?

You know, the conversations we wish we could have but we don’t know how to have. You as the inviter, the curator of conversation, the impresario… that’s your job. It’s your job to make people just uncomfortable enough, but still vulnerable in a way they wish they could be more often.

If you’re going to go through the effort of creating space. Of sitting down at a table with people you want to know. Of caring…

Why wouldn’t you ask the questions everyone wishes you would ask?

In this crazy, damaged, scary world. This promising, hopeful, growing world… We need connection. We need to feel known. And yet we continue to build barriers to deep, meaningful connection. The only way out is to step up.

It’s your job to create space for that connection amongst the people you care to know. It’s time to say, “I think people like us should do things like this. Will you join me?”