Awhile back I did a thought exercise. The exercise was a way of seeing what you valued most in life. It goes like this:

Every day for a week, write down the following snippet and answer it ten times:

Something I really want out of life is…

It seemed interesting, and I like it when things are spread out over a period of time so that you can see yourself in different ways. So I did this off and on for a few weeks. I expected that depending on the time of the day and my mood that this would fluctuate quite a bit, but I was surprised to see some recurring themes and a strong direction.

One of the things that struck me was “Something I really want out of life is to have meaningful conversations”. I put this down a few times, but I never really defined “meaningful conversation.” Perhaps I knew what I meant, but perhaps I didn’t and was just being vague. So I thought about it for a bit.

Meaningful conversations are one of the most desirable events that I can think of. If I knew that I would have a great conversation but I had to miss something else to have it, there are few things that I would rather do with that time. Of course, this rarely happens in practice because there is a certain degree of spontaneity, it just so happens that two people are walking along similar paths in life, considering the same problems or running into the same obstacles. It is, of course, possible to be too analytical, and thereby spoil things. As with anything that is desirable, it is advisable to not become too attached to previous experiences and expectations.

Sure, there are standard conversations that people have, but how many conversations do you have that change your life? That change your way of thinking? Is there a limit to how many meaningful conversations a person can have in a lifetime, or is this capacity without limit for someone that has a certain perspective or skill set?

Perhaps this is a high bar, but it is something to strive for. There will inevitably be conversations that are merely transactional in nature. “I’ll have that.” “Two dollars.” “Thanks.” “Thanks.”

And, of course, to get to a level where you can converse deeply with someone, there has to be a degree of rapport.

So with that in mind, what are the qualities of a good conversation? I have come up with a few indicators, mostly dealing with the sum total of the conversation. Seeing the whole for what it is and the synergy is the most important. For now I’ll just address conversations that have two people involved.

The very highest value that can come of a conversation is when two people discuss something and both understand each other’s perspective more clearly than when they began, and even come to a new understanding together. You don’t necessarily have to agree at the end of the conversation. There is a give and take with the conversation, mutual respect and a sense of discovery, acceptance.

There needs to be a sense of space, which is important to feeling comfortable and being able to explore thoughts and ideas without fear of judgment. This can take physical space in terms of environment and natural pauses, as well as emotional space. You don’t feel like your conversation partner is going to talk over you or that you have to rush to say what you would like to say. Space means you are listening. A conversation where one party isn’t listening isn’t a conversation. Periods of silence give time to internalize what is being talked about.

Good conversations are recursive (you can also view this as a stack.) A question or topic is raised, and tangents occur along the way, but at least one of the people is composed enough to steer the conversation back to the previous topic. This allows the conversation to flow but still explore all thoughts on the subject so both people feel validated. While the conclusions of the discussion cannot likely be foreseen by either party, in retrospect the conversation will have an orderly structure.

You are likely to be surprised by good conversations more often than you will anticipate them. However, I think that there are ways to attract them. Probably the best way is to have more and deeper relationships. I probably have some work to do on this front. See each interaction you have as a way of exploring reality, to see what others hold as their mental models and find interest in their beliefs. Time constraints seem to be inimical to exploring thoughts. Another way to attract meaningful conversations is to be serious and yet playful at the same time. It’s hard to open up around the permanent philosopher, and tough to interrogate reality with someone who always kids around. If something is on your mind, someone else has thought about it before.

Perhaps the most aggressive way is to talk to people that you don’t already agree with, to read books that you believe advocate an untenable position. What do you know to be true? Those are the thoughts that must be explored, that must be compared with reality and other interpretations of events. What if these beliefs were not true? What would it mean if you could set aside your beliefs long enough to entertain another beliefs, and thereby gain another useful way of looking at the world? The point isn’t to shoot down, the point is to understand. It’s not a zero-sum game.

Understanding fully another person’s position takes listening and an open mind, both of which are sometimes difficult for me depending on my state of mind and the immediate environment. Again, this doesn’t mean that you have to agree with the other person wholeheartedly, just that you are able to hear what they have to say and explore the ramifications of that world view. To be self-confident and flexible enough (understanding your own defense mechanisms and self-imposed limitations) to explore someone else’s views without negative emotions can be difficult, but it represents a growth opportunity.