Having a conversation is challenging. Most of us do a fair to middling job of it, and we can do a lot better.
We’re not taught to talk with each other. If we are taught to talk, we’re taught how to lecture (this is a lecture) or recite or report. Some people get taught to listen, which is good as far as it gets you, and is an important step toward learning to be a better conversationalist, but employing listening by itself can leave a conversation feeling lopsided.
I like conversing. I like having all participants contributing, having those contributions heard, and merging them into the conversational thread. I like conversing with people about deep, meaningful parts of their lives. To do this requires conscious involvement of the other people, because when people are sharing deep, meaningful parts of their lives, they depend on the other people in the conversation to support them.
In an attempt to have more deep, meaningful conversations with you, and for you to have more of them with your own circles, I have put together an overview of some of the key parts of having a successful conversation, written as a how-to and pulled from a number of sources.
Do these steps in order. You may have to repeat them many times during a conversation. Don’t skip around unless you know what you are doing. The better you know someone, the more important it is you do these, so don’t think you can skip them because of that.
1. Acknowledge: During listening, show the speaker you are listening through back-channel methods that don’t contribute meaning. Nodding, appropriately timed “uh-huh”s, eye contact all work in person. Online this is difficult. But you’d be surprised by how far an “I hear you” can go. Even when both people know what it means. Especially when both people know what it means.
2. Mirror: After an appropriate chunk, mirror: demonstrate that you have heard what they said and also understand what they mean by it. Your goal is to reflect back to them an image of themselves in you.
This can be as simple as parroting back what you think you heard, with enough space to allow for misunderstandings. (“It sounds like the coffee pot was being frustrating.” rather than “You are frustrated by the coffee pot”, which is disastrous if you’re wrong.)
Building meaning is a cooperative process. Your check is itself subject to misinterpretation. Depending on situation, a simple clarifying question may work: “Our coffee pot?” When all else fails there are stock questions to get people to say more, which may help you build meaning; dangling questions (where you purposely don’t finish the…) are also sometimes useful here.
3. Merge: Your goal is to join the speaker in their topic. I liken it to merging into traffic. Yes, you can drive onto the highway at 30 mph, but it’s incredibly rude, and if someone did that…
It may mean mirroring the person’s affect (emotional state) to a degree–telling someone who is riled up “Calm down, it’s not that bad…” is really dismissive. An enthusiastic “Wow!” (possibly followed by “You’d think they’d make better coffee pots!” or some such) may unhook them from the upset-train and let them actually talk to you. If you don’t acknowledge their emotions, they may end up getting more and more and more upset trying to make sure you understand they’re upset.
Stay on the subject they brought–or if you MUST change subjects, do it after merging, and with acknowledgement you’re changing the subject. Remember that feelings about a topic are a separate topic than the topic itself. Someone who is telling you about their broken coffee pot may be asking you to acknowledge and reflect ‘I am frustrated about the broken coffee pot’ before, instead of, or as well as, ‘the coffee pot is broken’ or ‘I don’t have coffee’.
Crucially, this includes talking about yourself if the other is person is talking about themselves–and most people are. “Oh, I solved that problem completely differently” is a common misstep (you’ve jumped to the topic of ‘you’). So is “Your problem is solvable in this way” (you’ve skipped over the potential frustration-topic). Not to mention “You shouldn’t feel bad” (which, in addition to being dismissive of their emotional experience, is about your judgment of their feelings); and a bunch of others.
4. Do The Work: After acknowledging, mirroring, and staying within the subject, work with the person to identify next steps. This might mean doing nothing; many successful conversations end with a report out and no action in response. “Mmm! Damn!” (or “Those weasels!”) could be your entire contribution and still be incredibly valuable.
If you’re not sure–and if you’re not reading this guide and having your neck snap off from nodding, odds are you’re right a lot less than you think you are–ask. “So do you want advice here, or are you venting, or is there something I can help with?” At this point you’ve built a conversational frame and some trust, and this question is less out of place than it might seem.
5. Adjust: As a part of a larger frame, if you feel like there is an imbalance or an unsatisfactory dynamic between you, follow up about it. For example, say a person always comes and cries on your shoulder, you don’t say anything, and then they leave before even asking about your day. It might be directly after having a successful or unsuccessful conversation. Stay away from accusatory (it’s counterproductive when you’re trying to change behavior or expectations) and aim for inquisitive.
A blunt adjustment might work for you, or might be better than nothing–at least you’re talking about it. “If you’re going to come in here and unload these problems on me, then I want something in return.”
Addressing the topic in a less loaded fashion may work better:
“I hope that I’ve been helpful. It seems like there’ve been a few times when you were able to come to me to talk about problems in the past.”
(wait for nod or other acknowledgement)
“I was wondering if you’d be willing to help me out with something in the future.” or: “And I was wondering if you had other people you can talk with also, when I’m not available.” or simply: “And I’m wondering how that was going for you.”
(listen for answer, gauge ability to effect behavioral change at this time)
The important part is to take the time to talk about how things are going with the other person. Is this conversational style working out? Would you or they like other changes? Conversation can itself be a wonderful topic of conversation, letting you refactor an otherwise strained, unpleasant, or inefficient relation.
Try it, observe, improve
This isn’t the last word on having a great conversation. These steps are all filled with gotchas, and have to be practiced to have good impact. This is a skill, and like any other skill, you won’t improve if you don’t practice. And an important part of practicing is observation and adjustment. This is where Adjust can really help–talking about the conversation itself with a willing partner may help you identify areas you can improve.
The steps may seem artificial–and breaking them out this way is a bit artificial. Like any skill, you learn it in parts and then you put the parts together, and before you know it you’re fluent.
And some people aren’t interested in conversing in these terms (or may not be at the moment). They may be too upset, may want you to skip straight to solution space, or maybe they just want you to roll over and be cowed by them. Some folks are raised to avoid this sort of conversation, instead taught that conversations should be as short as possible, or should consist of ‘telling’. Some people are simply abusive and don’t care to have a two-way conversation. Or you may be in the throes of a Difficult Conversation, one where your self-image (or theirs) is at stake. If you’re trying to build a common ground using the above method, and it isn’t happening, don’t be too discouraged; try to identify how things are unsatisfactory, and if possible, what happened. These steps are a framework, not a prescription.
So try it out! Let me know how it goes.
 This is my synthesis of a variety of sources. I’ve learned a fair amount about active listening, negotiation, Rogerian argument, and plain old ‘getting along with people’. I’ve recently participated in workshops on some of this. Some of it is based on topics from the excellent book “Difficult Conversations“. It’s also based on what has worked and what hasn’t in my own experience: it is a big part of my day job to have successful conversations with people about tough topics, and it is a crucial part of my private life as well. I am lucky to have a bunch of good conversationalists around me at work and at home, people to work with on these skills and to demonstrate good practices. Finally, it’s a skill I’ve had to spend time and effort learning, which makes me more aware of how to learn it and what the moving parts are.
 You can skip some steps due to prior agreement, or due to the context: fighter pilots in a dogfight probably won’t say “I hear ya, sounds like those MiGs are really frustrating you. So, I know we were talking about you, but if you get a chance, I have something I was hoping I could mention–could you come around and protect my six?” But I’m going to guess that you are not in a dogfight.
 For more on co-construction of meaning, you may be interested in researching the fields of Conversation Analysis and Discourse Analysis. Specifically, I am thinking of the concept here of “least collaborative effort”, postulated in Herb Clark and Deanna Wilkes-Gibbs’ 1986 paper “Referring as a collaborative process”. This is an amazing paper detailing how conversational participants will depend on their partner’s knowledge of the situation to establish meaning; there’s a decent Wikipedia article on it.
In a nutshell, if I say, “That red tree’s got pretty leaves”, you can infer that I am referring to some tree that I expect you to be able to see; it would be quite unfair of me to refer to some tree you couldn’t see. This narrows things down to red trees you think I think you can see. It’s in lieu of having to formulate some horridly complex reference like “The tree on our left, twenty feet out, which has red leaves”–collaboratively, we can depend on each other to help build meaning. If I then say, “the tall one?” I am demonstrating understanding in a minimal amount of effort–I expect that you can discern which tree I think is tall. This lets us continue our conversation without wasting all our energy constructing unambiguous references–and the crucial step, which makes it all possible, is demonstrating understanding.
Side note: this paper applies the same principles to human-computer interaction. Fun stuff!