Personal Improvement

The Art of Meaningful Conversation

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Small talk only gets you so far. If you want to improve your career, your relationships, and your life, you have to move past small talk to something deeper. Today we interview two experts on the art of meaningful conversation.

Mollie Kinsman Khine and Taylor Buonocore are the inventors of  Convers(ate), a game designed to spark conversation.

The Lost Art of Conversation

Why have our conversations become so “surface,” often rarely moving beyond mundane things like the weather or what the local sports team is up to? Partly thanks to things like texting and social media; neither medium is conducive to meaningful conversation.

Maybe also because people have become more and more contentious when their opinions differ. We used to be able to have a civil, meaningful conversation about topics we disagreed on but now we either avoid those kinds of topics because the conversation degenerates into a shouting match or we’re simply too afraid to bring them up at all.

Jeffersonian Dinners

Thomas Jefferson hosted conversation focused dinners. A small number of guests from all over the country (which was a bit smaller then) would meet to discuss one topic. The guests spoke one at a time, everyone listened and participated, and the goal was that each guest would learn something and take it home and share it with those in their community.

If you want to host your own Jeffersonian Dinner, these are the rules;

  • 8-14 guests from diverse backgrounds. You don’t want a roomful of doctors from Michigan. You want a mix of races, careers, income levels, genders, and political affiliations.
  • One topic. It can be anything but should be something that will have some relevance to each guest. The topic should be revealed before the dinner so the guests will have some time to ponder it and what they might like to discuss.
  • Five to seven questions that will help move the conversation forward.
  • A facilitator to keep things on topic and flowing along.
  • Food and drinks. Neither have to be fancy, you can order some pizzas and buy a few bottles of wine. The food is not the focus of the evening.

Each guest starts by sharing a little about themselves and how the topic is personal to them. Everyone is allowed to speak without being interrupted but the facilitator may need to prevent some of the guests from dominating the conversation and not giving others a chance to speak.

While there is some structure, in the beginning, the rest of the conversation is allowed to flow naturally.

At the end of the night, each guest shares something they’ve learned and can propose a potential topic for the next dinner.

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The Game

This all sounds great, you want to host your own Jeffersonian Dinner! But it can be a little intimidating. What if you can’t think of a topic, or can’t think of any good follow up questions? That’s why Convers(ate) was invented.

There are 28 topic cards in each box; some are lighthearted and some are more thoughtful. They include topics like wealth, endurance, and parenthood. Each topic card has questions meant to explore it from different angles. The wealth card, for example, asks things like the difference between wealth and money, wealth as legacy, and how people manage their money.

The questions aren’t random or disconnected from each other. They are designed to engage the guests on one topic but without letting the conversation get stale or repetitive.

Why Having the Right Conversations is So Important

Conversation generates opportunity whether it’s the opportunity to make more money, find a career you actually care about, to improve your personal relationships, or find out about a great new restaurant. The more you talk and more importantly listen, the more opportunities that come your way.

That’s why networking, a word I think we all hate, is a good way to find a new job or a new partner. The person you chat up next to you at the bar or the copy machine might know of or be, both. How can you get better at having more of the right conversations?

Baby Steps

It’s hard for some of us even to make small talk but it’s the first step to more meaningful conversations. There are baby steps you can take to get you there. Have a few “back pocket” questions that you can use to get a conversation started.

The questions don’t have to be deep and meaningful and those kinds of questions aren’t really an appropriate opener to the person next to you at the bar or standing next to you in the buffet line at a conference. The question shouldn’t be cliched either though so nothing about the weather or career.

The question can even be a little out of left field, try asking what the person had for breakfast or what has been the highlight of their day (meeting you, obviously!). Something silly catches people off guard, makes them laugh a little and that helps lower the auotomatic defenses most people have when they’re approached by a stranger.

The question should be one that allows the person to tell a bit of their story. What a person eats for breakfast can tell you a lot; they’re trying to lose weight, they’re Paleo, Vegan, an intermittent faster, they’re an early riser or a late sleeper. Each of those things is a tiny part of someone’s story and if you pay attention, you can go from there to continue the conversation from small talk to a deeper discussion.

The main thing that keeps most of us from starting conversations with strangers is the fear of rejection but most people will be glad someone broke the ice. No one likes to feel like the kid sitting alone at the lunch table.

Those Awkwardard Pauses

Even good conversations can contain awkward pauses and they’re usually longer and more awkward inside our own heads than they are in actuality. Asking open-ended questions is the best way to avoid and get through the pauses.

If you ask what someone ate for breakfast and they stonewall you with “cereal,” you can ask a more open-ended question as your follow up. Do they eat cereal every morning or make something more elaborate on weekends? What kind of cereal? Is that your favorite or it just happened to be what you had in the house?

Keeping People Engaged

Keeping people engaged in conversation with you is more about listening than talking. People looove to talk about themselves, even the self-proclaimed introverts. Your curiosity about others is your secret weapon. People are weird and smart and funny and interesting and engaging when they feel as though their listener is curious and interested. Listen more than you talk. 

Look at people when they are speaking to you, don’t slide your eyes to the left to see who else is in the room. Lean in and nod your head from time to time. Don’t rush the conversation.

Unless you have zero interest in continuing the conversation, never say things like, “Anyway.” That is a death knell. There is no good way to interpret an “anyway. It either means you’re bored with the topic and want to change it or bored with the speaker and want to get away from them. And maybe you do but there are more gracious ways to do it.

Sprinkle the speaker’s name throughout the conversation, not only does it make them feel special, it helps you remember their name which is a problem for some of us. If you’re in a group and there is someone kind of on the fringe not saying much, verbally invite them in, ask them a direct question and address them often.

How to Approach Difficult Topics

Sometimes you have to have the tough conversations. No one likes them but there are ways to make them more productive and less destructive.

We’re vulnerable when we have these kinds of discussions with loved ones but there is nothing wrong with that. Unless the person is a psychopath, a loved one won’t pounce on a vulnerability. They’ll want to assuage it and reassure you. It also shows trust which helps to build relationships and thus the conversations within them.

Some of us avoid asking questions because we’re afraid to look dumb. But asking questions is how you learn things and people love being asked for advice. There is that old cliche about the fastest way to get the right answer to anything is to post the wrong answer somewhere on the internet. People will come out of the woodwork to correct you.

How to Disagree

Sometimes there is just no coming to an agreement on a subject. You still have to have the conversation though. For most topics, there is no right or wrong answer. That means that no one has to “win” in these kinds of discussions.

Be respectful and listen to what the person is saying. They didn’t arrive at this opinion from thin air. This opinion has been built on their own experiences throughout their life and that alone makes it valid.

Be respectful. Hear what they say. The goal of these conversations should be that each person is understood by the other, it’s not to agree or to find a solution immediately.

If things get really tense, acknowledge the tension. Allow for a break so you can each think about what you said and what was said to you.

Practice, Practice, Practice

Being a good conversationalist is like being a good anything else, it takes practice. If you’re a hardcore introvert, we don’t expect you to take all this great advice and saunter into the nearest bar to try it out for the first time.

That’s why the ladies invented the game, so you can perfect your technique in the comfort of your own home on your close family and friends. And what you learn about those closest to you might surprise you and deepen your most important relationships.

Show Notes

Truck Stop: A honey brown ale.

Conversate Kickstarter: The campaign is live until November 10, 2017.

Convers(ate)’s Website: Check out the details of the game.

Tool Box: All the best stuff to manage your money.

Investable: Research and evaluate rental properties.

Candice Elliott - Senior Editor
Candice Elliott is a substantial contributor to Listen Money Matters. She has been a personal finance writer since 2013 and has written extensively on student loan debt, investing, and credit. She has successfully navigated these areas in her own life and knows how to help others do the same. Candice has answered thousands of questions from the LMM community and spent countless hours doing research for hundreds of personal finance articles. She happily calls New Orleans, Louisiana home-the most fun city in the world.

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