Choosing when to go deeper in conversation

I've been thinking lately about the moments in a conversation when the people participating make a choice - conscious or not - about whether to let it go "deeper," or to keep it at a pleasant and polite level of chit-chat. I'm exploring that because (A) I really enjoy deconstructing how we communicate with each other, and (B) I want to take responsibility for my own part in the cases where more depth would have been a good thing, but was avoided. (I even kind of wrote a little poem about it a few years ago.)

I put "deeper" in quotes because it's one of those touchy-feely words that needs a little more definition to be useful here. When I think of a conversation reaching a new depth, I think of the people involved taking on topics that are significant or meaningful to them in ways that invites personal vulnerability or reflection, where you might have to take a stand, where the stakes are higher and there is something to gain or lose by going there. The topics that achieve this will of course vary widely by personality, community and culture.

So, what do those turning points look like? Here are a few I've noticed:

1. Those in conversation realize a new common ground. If you're talking and you find out that the other person has had some experience, insight, or wisdom that connects with an experience, insight or bit of wisdom you've gained, it can open up a sense of possibility about where the conversation can go. "Wait, you've been through that too?" or "Wow, it sounds like we both think the same way about that complex issue!"
2. Those in conversation realize an unexpected conflict. If one person says something that runs up against what another thinks or feels, we have the choice to engage that - "Wow, I really disagree with what you just said!" - or to let it go, usually through silence, vagaries ("I see what you mean"), a change of the topic ("Well, I don't know about that, but did you hear about..."), or even lying ("Yeah, totally!"). I've already written some too about how challenges in conversation can play out.
3. The depth of conversation implies or dictates the depth of the relationship. There are some kinds of sharing or engaging that we only do with people with whom we have certain kinds of relationships. If the conversation is headed in a direction that asks us to take on a new kind of relationship with the other person, we have a choice to make about whether that's desirable. For some this is an easy choice, because they tend to be good at being in relationship with people "in the moment," independent of any thoughts about future closeness, whether or not you'll stay in touch, who else they might tell, etc. For others, reaching a new depth requires some sense of accountability and trust that's built over time. So the choice about a conversation can be the choice about the future of the relationship with others participating.
4. A transitional moment in time arrives. Sometimes the choice about whether or not to go deeper is thrust upon us by some external happening. "Oh, well, now that we're done with dinner, it's a natural time to get up and leave...or we could stay and talk more." Of course the choice here will usually be wrapped up in what kind of conversation is happening when the milestone is reached. For me, I have noticed that when I allow for the possibility that just because it's a natural time to have closure on the conversation doesn't mean we have to, I've ended up having some rich conversations in the "next phase" of the time together.

So, those are some of the critical moments I've noticed. I'm curious to know what others think about when and how those choices are made.

What kinds of environments or states of being or topics or relationships allow you to go deeper, and what kinds keep your conversation "at the surface"?

I’m a journalist, publisher, software developer and entrepreneur with experience as a founder and organizational leader. Work with me or learn more about me.

Did you enjoy this? Subscribe to new posts, or follow me on Mastodon @ChrisHardie.