How To Have More Meaningful Conversations

The other morning I sat down to map out my perfect day. I won’t bore you with all the minute details but one part of my perfect day is sitting down with a friend or stranger over a cup of coffee and having really meaningful conversations.

Meaningful conversations to me are where the other person shares ideas, thoughts, stories, and theories about life and their experiences that get me to see past my own personal biases – not necessarily to change them but to get me to evaluate and think about them. Hopefully, I can do the same for them.

Meaningful conversations put me in a flow state. Flow is a term coined by Mihaly Csikszentmihalyi (good luck with that one). It’s that moment when you’re totally absorbed in what you’re doing that you forget about yourself. Time seems to fly by, you lose yourself in the moment, and you just zone out.

It almost sounds like a state of unconsciousness. But in reality, it’s an elevated state of consciousness where your awareness is at such a heightened state that it feels like you’re completely on another level. 

But that’s just me. What do you look for in a good conversation?


It might be weird to think about conversation as an art but it is. 

Art is the expression or application of human creative skill and imagination, typically in a visual form such as painting or sculpture, producing works to be appreciated primarily for their beauty or emotional power.

While a conversation might not have as much visual impact; outside of looking at the person, you’re speaking with. I’m sure we can agree that they are very creative, imaginative, beautiful, and contain plenty of emotional power.

So how can you create more meaningful art – in this case, conversational art?

Manage your expectations

Recently I was out with some friends and they were discussing their favorite IPA’s. I haven’t had a beer in about 15 years and had no clue what they were talking about – secretly wishing the conversation would turn to wine so that I could contribute something. But it didn’t.

There are a few things you can do here.

You can totally zone out, nod your head randomly every once in a while to pretend you’re engaged, and maybe laugh awkwardly, or give a few yeah’s and mmmhmmm’s.

Or you could participate and be interested in asking questions about what they’re talking about. After they were talking a bit I got the courage to speak up and say, “Hey fellas, I haven’t had a beer in like 15 years. Could you explain real quick to me what an IPA is?” After they all looked like this at me I was surprised at how interested they were as to why I haven’t had a beer in the last 15 years. They explained what an IPA was to me but the conversation quickly turned to why I wasn’t a normal human being. Lesson learned – just be honest. Your insecurities maybe a cool topic of conversation.

Oh, and if you’re wondering, yes I did try an IPA that day. It was gross. I had a few sips and kindly offered that bad boy to one of my buddies.

Now, this goes both ways. You may be having a conversation about the new movie, a video game you’re playing, a recent Paleo recipe you tried, art, literature, sport you love, or the trip you just took. There’s a good chance the person you’re talking to may not have any idea what you’re talking about. Make sure you manage your expectations for how they should contribute to the conversation – it may be a lot, a little, or nothing at ll.

Practice Self Awareness

Conversations typically are conducted in 1 or a combination of some or all of the following ways.

I-I Conversations – Not seeing the other person and just seeing yourself. Unfortunately, I’m notorious for this and have been actively trying to improve it. This happens when someone is talking and you stop listening because you’re trying to think of the next thing to say.

I-IT Conversations – These conversations are all about a means to an end. For example, you may have a conversation with your boss about getting a raise, your girlfriend about breaking up, the dealer down the street (car dealer not a drug dealer) about lowering the cost of the car you want to purchase.

I-Ghost Conversations – Not seeing the person you’re talking to but instead a ghost of your past. Oh believe me I have definitely done this before and I’m sure you have as well. 

I-You Conversations – These are the Care Bears of conversations. These are the conversations that make you all kinds of good inside like when you used to climb the rope in gym glass – that was a joke that probably only the guys understand.

The I-You conversations are the types of conversations that you want. A mutual sharing of ideas, thoughts, and emotions. These are those conversations that “flow.” For example, a few years back a friend of mine came over to the house and we poured ourselves a glass of wine and sat in my kitchen and just chatted. We talked about love, relationships, travel, and a host of other things. We were both open, honest, and vulnerable – allowing the other person to speak and taking a few seconds to respond instead of trying to get in the next word.

How easy do you find it to have I-You conversation? 

Embrace The Silence

I’ve always been a little uncomfortable with silence. It’s awkward, uncomfortable, and just plain weird.

Being uncomfortable with silence is what can lead you to ignore what the other person is saying and instead of trying to think of the next great thing you can say. It can also rush you into a response without really thinking about whether it’s an appropriate one. 

Conversations can sometimes be difficult and part of that difficulty is with the silence that may come. Poet Parker Plamer writes:

In our present culture, silence is something like an endangered species…an endangered fundamental. The experience of silence is now so rare that we must cultivate it and treasure it. This is especially true for shared silence.

Sharing silence is, in fact, a political act. When we can stand aside from the usual and perceive the fundamental, change begins to happen. Our lives align with deeper values and the lives of others are touched and influenced.

Silence brings us back to basics, to our senses, to our selves. It locates us. Without that return, we can go so far away from the true natures that we end up, quite literally, beside ourselves.

We live blindly and act thoughtlessly. We endanger the delicate balance which sustains our lives, our communities, and our planet.”

Like Palmer says above, embracing the silence can bring you back to the basics of not only conversation but life in general. 

Accepting silence is a difficult task but give it a shot today. In the next conversation, you’re intake 10 to 20 seconds to respond after someone is done talking. You can use this time to consider your response or to simply soak in what they have just said. 

Sometimes the most meaningful conversations are often the ones that we don’t have.

Have More Adventurous Opening

How many times is this week where you asked, “how’s it going?” Or maybe on Monday, “how was your weekend?” Boooooooooring!

These canned questions get canned responses. 

  • Good
  • Fine 
  • It was ok
  • It’s going well
  • Same old same old

Let’s be honest. Most of the time when you ask these questions you’re either just doing it to be nice and don’t really care about what the answer is – you expect it to be short and sweet like those above – or you ask the question and totally zone out because you already know the response it going to be one of the examples above.

Add a little sum’n sum’n to these boring conversation starters. How was your weekend can turn into:

  • What have you been thinking about this weekend?
  • What was your favorite part of your weekend?
  • What was your favorite taste this weekend?
  • If you had to do your weekend differently what would you do?
  • What was the highlight of your yesterday?

When conducting interviews Peter Theil likes to ask, “Tell me something that’s true, that almost nobody agrees with you on.”

What are some ways you can make your conversations more unique and adventurous today? Can you use the environment or context of a situation you’re in? What about a dream? What’s something you’re struggling with – that they’re struggling with? What fear, embarrassing moment, or belief of yours and theirs that you’d like to explore?


difficult conversation

In 2011 a gentleman by the name of Jon Underwood started the first Death Cafe at his house in Hackney, East London. 

I know what you’re thinking, “Death Cafe? WTF is that?”

A death cafe is a place for friends or even strangers to eat cake, drink tea, and discuss death. The objective is ‘to increase awareness of death with a view to helping people make the most of their (finite) lives’. A Death Cafe is a group directed discussion of death with no agenda, objectives, or themes. It is a discussion group rather than a grief support or counseling session. 

Sounds weird, right?

That’s what I thought too until I really sat to think about it. What a Death Cafe is actually doing is taking an often difficult and awkward subject to talk about and put it in an environment that makes it comfortable and ok to discuss.

“When people sit down to talk about death, the pretense kind of falls away, and people talk very openly and authentically,” Underwood says. “And they say things in front of strangers which are really profound and beautiful”Jon Underwood, in an NPR interview

When you’re having difficult conversations do your best to set up an environment that makes those conversations comfortable, safe, and welcoming.

Also, understand the limits of your own experiences. You may not be able to help a friend get through their depression, breakup, or struggle with weight loss and that’s ok. It’s not your responsibility to solve every person’s problems you come into contact with. Remain who you are and let others be who they are – their issues are their issues and your issues are your issues.

Sometimes the best thing you can do is just be there for them when they want you, to listen actively, and practice empathy by putting yourself in their shoes.

Difficult conversations are always going to be, for lack of better words, difficult. By being clear about your needs, not trying to change the other person, and being an expert on yourself you can contribute positively to them without making them any more… difficult.


Julian Treasure gives a great talk about how to have better conversations. In it he mentions some obvious things like staying away from gossip, judging, negativity, complaining, excuses, exaggeration, and dogmatism – He also gives us a simple formula he calls H.A.I.L  for having better and more positive conversations.

  • H – Honest: Are you having conversations you actually want to be having and also being honest, open, and vulnerable in them?
  • A – Authentic: Are you being true to yourself and showing that to the person that you’re conversing with?
  • I – Integrity: Are you living up to your word and valuing your values, principles, and priorities?
  • L – Love: Are conversing in a way that takes into account the other person’s well-being? 

With that formula in mind what are some conversations you really want to be having and which ones are you not having? Work, health, death, love, God, stress, sex, money, or maybe something entirely different? Let me know in the comments below and let’s start a meaningful conversation.


Photo – Anna Vander Stel, Photo – Korney Violin