Conversation and the conversationalist: probably one of the most under-discussed topics in the social arts. What a pity. Conversation is part of the backbone upon which everything related to socializing is built upon, but in the 21st century that’s almost forgotten. You might go so far as to say that the art of the conversationalist is a vanishing art.
In this day and age of sound bites, quick blurbs of news, and friends and acquaintances using social media to spit out short, tepid, meaningless quips about their days and feelings and whatever else springs to mind and gets unloaded out on the uncaring and overburdened ears of the Internet, being a good conversationalist is a rare thing. Being someone who is able to deftly move from topic to topic, keeping a conversation flowing effortlessly and breezily forward, diving into the depths of another individual’s personal life and concerns, then coming back up for air with a bit of laughter and lightheartedness before things get too heavy, then diving back down again to find out more about this person you’ve met just an hour ago than his or her closest family members know… this is what the lost art of being skilled in conversation is all about.
The conversationalist moves past small talk with ease. The conversationalist elicits emotions and feelings about topics his conversation partner didn’t know she had. The conversationalist dives deep and gets to intimate, personal topics that allow him to really relate to others and bond to others, and allow others to really relate to and feel bonded to him. The conversationalist does not just talk; he drives a conversation from the initial feeling-out stage to a deep, personal connection that is rewarding to everyone involved.
It isn’t easy to become talented at conversation. Actually, it’s rather challenging, sometimes emotionally draining, and always a constant work-in-process, even for those who’ve been focused on improving their conversational aptitudes for years. But it’s very worth it; learning to excel in conversation is one of the most excellent, useful, empowering skills you can possibly learn.
Being good at conversation opens doors for you that few other things can.
Before we discuss how you can start on the path to becoming a truly world class conversationalist, though, let’s start by covering everyone’s favorite part first: the benefits to you.
Benefits of Being a Good Conversationalist
So let’s say you put in the work, and actively hone your conversational abilities, and start really paying attention to what you’re saying to people and what they’re saying back to you and start trying to actively drive conversation to more effectively get more and better information from others. How’s that do you any good?
Well, the thing about conversation is, unless you decide the hermitic life is the life for you, you’re going to be using conversation everywhere, constantly, with just about everything you do in life.
You use conversation everywhere.
Because it’s so ubiquitous, you’d think it would be a no-brainer that of course their abilities as a conversationalist would be one of the first things people focused on. But life is funny, and beyond a certain level of ubiquity, people stop working on things.
To put it in perspective, I’ll ask you this: when’s the last time you worked on the way you walk? How about your voice tone – have you worked on that lately? If you drive a car, have you sought to get better at driving any time recently? If you ride a bike, have you actively worked on becoming a better bicyclist in the past year?
If you’re a highly self-improvement-focused person – which, if you’re reading this blog, I’m betting you are – then you may very well have worked on some of those things. The vast majority of people out there have not, however, for this simple reason:
The more you’re exposed to something, the more “natural” it feels, and the less it feels like a “skill” you should work on developing.
It doesn’t feel like a skill, because you do it all the time. But could you get a stronger, more powerful, sexier walk than you have right now if you worked on it a little? Could you get a sexier, edgier, more commanding voice if you put some effort into it? Could you become a better driver or a better bicyclist if you actively tried to?
I’m betting you could.
Conversation is more nuanced than any of those, though; it’s made up of more variables, there’s more to keep track of, and it changes quite a bit depending on whom you’re talking to. Driving cars is always pretty much the same; sometimes it’s daylight, sometimes it’s nighttime; sometimes there are more cars or sometimes less; sometimes there are two lanes or three lanes or sometimes just one. But the variables are small and manageable.
In conversation, though, the conversationalist must manage a whole host of things. He has to manage how he’s feeling, what he’s expressing through his words, voice tone, and nonverbal communication, he has to read how others are feeling and what they are expressing, he has to steer the conversation so that it stays on productive and value-building topics and avoids destructive ones, he has to reward others’ efforts to contribute and provide value and remove embarrassment from them when they slip up and make a faux pas. And that’s just for starters.
So, being a talented conversationalist becomes one of those things that’s exceptionally rare. It’s quite uncommon to meet someone able to adeptly and adroitly navigate conversation – but it’s always refreshing when you do. Truly, hasn’t it felt great those few times you’ve met someone who was just so agreeable and pleasant to talk with and who made you feel accepted and understood right away and showed a genuine interest in you and curiosity to get to know you? You can probably count the number of people you’ve met in your life like that on one hand. Those people you’re thinking of were the good conversationalists.
Here are some of the benefits of being skilled in conversation:
- People just like talking to you. You’re fun, easy, and low pressure to talk with. Whenever they talk to you, they feel good, relaxed, and accepted for whom they are. You become a breath of fresh air from all the other people they talk to in their day-to-day lives.
- You get to know people very quickly. As a skilled conversationalist who’s mastered the deep dive, you quickly navigate down to the important stuff – stuff often others talk about only with their closest friends, or sometimes no one at all. This allows you to build a real connection and get past that awkward zone in a hurry where two people are talking but don’t really feel like they know each other.
- You make deep friendships fast. A consequence of getting to know people fast, and one of the amazing benefits to the conversationalist of his skill, is being able to build a lot of very rapid, but very genuine, friendships and alliances with people. When you’re a good conversationalist, you can cover twenty or fifty or a hundred times as much ground in an hour of conversation than an unskilled conversationalist can. While Joe Average is still figuring out what his date likes to do for fun on the weekends, I’ve found out that mine dreams of living in Rome and wants to open her own pastry shop someday after she leaves the corporate world. That kind of connection leads to real friendship, because people know what you’re about, and know you know what they’re about, and the two of you are then able to let your guards down around each other and just be comfortable and genuine.
- You get what you want a lot more. No sense denying it, simply for getting what you want from other people, being skilled in conversation is essential. Whether you’re trying to negotiate a deal or win over a potential new lover or talk your way onto an airplane that’s already finished boarding while you’re still at the check-in counter (as I have successfully done a few times in the past few years; that probably means I should just get to the airport earlier, though), the conversationalist is at great advantage over an ordinary individual who hasn’t put much thought or effort into improving his conversation. It gives you a decided, decisive edge that really is beyond valuable.
I’m probably forgetting half the reasons out there why you ought to invest in training yourself up in conversation, but you get the point. Conversation reaches tendrils into every aspect of your life; to ignore your skill as a conversationalist is to ignore one of the most significant skills you can possibly develop.
Makings of a Conversationalist
There is only one prerequisite for learning to be skilled in conversation, in my opinion: you must genuinely be interested in other people. If you aren’t, well, you can force yourself to a certain degree of aptitude by sheer willpower, but beyond that, you’ll have a hell of a struggle getting beyond an intermediate level in your conversational abilities.
However, even if you don’t find people terribly interesting at the moment, that may be simply because you haven’t gotten your skill at getting to know them well to a high enough level yet. Lots of people think golf is a terribly boring game, until they’ve played it enough times and get familiar with it. Then they come to find it quite engaging, and rather enjoy a good round of eighteen holes. Conversation and meeting new people may very well be that way for you later on down the road after you focus on upgrading your skills, experience, and exposure to it.
So, genuinely enjoy talking to people. You don’t have to genuinely enjoy small talk; me personally, I’m not a big fan of small talk, and I get past it pronto. What I’m really interested in is what makes people tick – what drives them, where are they going, where did they come from. Why do they do the things they do. This is the stuff a conversationalist is good at finding out.
Here are the skills I think you ought to focus on first when upping your skill tree. These are the building blocks everything else rests on in conversation:
- Get to the root. Conversation for normal people usually looks like this:
Person A: What do you do?
Person B: Oh, I’m an accountant.
Person A: I see.
Person B: And what do you do?
Person A: I’m an engineer.
Person B: Oh, okay. You must be good at math, then.
Person A: I’m okay at it. How long have you been an accountant?
Person B: About four years. And you, how long have you been an engineer?
And on and on. Ouch, that’s a painful dialogue; no wonder no one likes small talk. Small talk is boring. But why is it so boring? Look carefully at that conversation above, and you’ll notice it’s extremely surface-level.Nowhere do we get to the meat of emotions, feelings, dreams, motivations, a person’s backstory; the stuff that’s really, truly important to people. Person B may be an accountant, but her job as an accountant is not what defines her, and we don’t really know her all that much better by finding out that she’s an accountant and she’s been an accountant for four years. Here’s how we get to know her:
Person A: What do you do?
Person B: Oh, I’m an accountant.
Person A: Hmm, I see. Accounting… why accounting? Why not finance, investment banking… why choose the field you did?
Person B: Well, I guess… because it was an easier major to get into when I was in school!
Person A: Really? You’re doing the job you’re doing now because it was easier to get into in college? That’s crazy! How long have you been doing it?
Person B: About four years.
Person A: Wow, four years in a job because it was an easier major. Okay, well, tell me this: erase college. If you could jump into any job in the world, regardless of how easy the major was in college, what would you be doing other than accounting? Or is accounting your dream job?[said with a smile and a wink since you know it’s not – she’s already said she’s only in it because it was easy, and besides, who wants to be an accountant? (advance apologies to all the accountants out there who actually love it!)]
All the other guy managed to find out with his initial conversation was that Person B is an accountant and she’s been one for about four years. With the same number of lines of dialogue – count ‘em, there are four lines of dialogue for Person A in both conversation examples – our second guy has managed to find out not only that the person he’s talking to is an accountant and has been for about four years, but also that she’s doing it because it was an easy major in college, and it’s probably not something she really dreams about doing.
And now she’s going to tell him what she does dream of doing.
Not bad for four lines of dialogue. That’s what getting to the root is about.
- Help others think. Being a good conversationalist typically means you’ll be being a bit demanding of others, intellectually speaking. People prefer to talk about themselves, and conversationalists are talented at getting others talking about themselves, but people sometimes need a little help to avoid getting confused, frustrated, or worn out. Helping the people they’re conversing with to think more easily is one of the ways a conversationalist gets people talking more about themselves than they do when talking with others, and it helps prevent the person he’s talking to end up in a conversation that feels mentally taxing or draining.
If you noticed in the last example above, the question of, “Why accounting?” is fleshed out beyond just the words “why accounting.” We say “why accounting,” but then we also list a handful of suggestions and clarify the question – “Why not finance, investment banking… why choose the field you did?”
If you ask a question that’s too open-ended, people can feel lost in the spotlight. It’s like being on-stage without cue cards or a teleprompter; they’ve been put on the spot and start to panic mentally. When you phrase a question like how we did in that example, though, with a few alternative suggestions for what Person B might have done rather than accounting, and then give a specific question to jog her memory of what’s being asked, you light the path for her basically and make it much easier for her to come up with the response you’re looking for and answer your question.
The mind generally goes through a process like this:
Why accounting? Oh, I don’t know… Oh, why not finance or investment banking? Because I didn’t major in those in college. Why did I choose accounting? Oh, right – because it was an easy major in college. I didn’t major in those other ones because they were more difficult to get into and I was a little lazy in school.
And just like that, you’ve helped her think through her response, just by listing a few alternatives and restating the question. This is useful with a wide variety of topics:
“Why move to London, then? Why not New York, or Paris, or Tokyo? Why come here to London-town when you could go just about anywhere?”
“Why get your Master’s? Why not keep working, or use your spare time to travel the world or write a book? Why go back to school?”
“Why break up with your boyfriend? Why not marry him? Why not just keep seeing him the way things were? Why call it quits?”
All kinds of things you can use this for. The point is, you want to help people think more easily, and that gets conversation flowing fast and naturally and it frees their minds to process the more important, deeper aspects of the conversation since you’ve already handled the basic stuff for them and provided the framework to answer you with.
- Relate. Obviously, the flipside of things is that you don’t want this to be an interview. You need to be relating to what you hear from others. Balance is quite key here; you don’t want to overdo it and come across like you’re trying to impress or force a connection, but you also don’t want to underdo it and come across like you don’t relate and she’s talking nonsense to you that you don’t connect with.
This is where the “art” comes into play in the art of conversation. I wouldn’t be surprised if there’s a way of breaking down exactly what that balance is – we’ve done it for things as seemingly random as how many “I” pronouns versus how many “you” pronouns you ought to have in conversation (keep them as close to equal as possible), so there probably is a way. I just haven’t figured it out yet, and I’m not aware of anyone else who has either.
I’d say a good rule of thumb is to relate on things that you intuit someone else might be slightly embarrassed about; e.g., if you’re talking to someone and she mentions that she’s had so much bad luck lately, you commiserate and tell her you go through strings like that as well, where nothing ever goes your way; then you turn it back to her and ask her what good things have happened to her lately. Relate too on important topics; if the two of you have been talking about something that’s obviously important to her, and you haven’t related to it, you should.
Again, learning the proper way to relate in a convincing, genuine way without seeming like you’re trying to force things is going to take practice. I can remember a few years back when people would tell me things about themselves that I just didn’t know how to relate to. For instance, I had a 21 year old girl tell me three years ago about how her Navy ex-husband had cheated on her, and she found out, so she cheated back – I had no idea how to relate to that at the time; I think I blurted something out like, “Yeah, sometimes guys in the Navy, you know, lots of temptation overseas.” These days, I’d handle that easily: “Ah, people. They do crazy things, and some of ‘em you can’t trust farther than you can throw ‘em. What’re you gonna do?” But that’s just because I’ve been through enough conversations where I was struggling awkwardly to relate to something I didn’t really know how to relate to properly at the time.
Remember, relating is how you make people feel good in a conversation. If you don’t relate to them, they’ll feel like what they’re saying is falling on deaf ears, and they’ll start clamming up. The better a job you do relating, the more people will feel like you “get” them, and the more they will want to tell you about themselves to help you understand them even better.
- Turn it back to her. Most men, you get them talking about themselves, and it becomes a spout that just doesn’t shut off. There’s this voice in men’s brains that seems to say, “I must position myself as impressively as possible; I must show people how amazing I am!” Men thus feel compelled to tell everyone who will listen how wonderful and cool and successful they are, and show this off through stories of their successes and tales of their feats.
Good conversationalists? No such penchant. Ask a conversationalist what he does for a living, and he’ll build some intrigue with a short, interesting-sounding reply. By way of an example, people ask me what I’m doing right now, I tell them I’m traveling and finishing my first book. I also have a few startup companies I’m launching, but I don’t typically tell them that until later on, because traveling and writing a book is intriguing enough in its own right. After I tell them that little snippet about myself, I then turn it back on them.
“How about you, how are you spending your time these days?” I’ll ask.
The conversationalist should spend maybe 20% of a conversation talking about himself, and 80% of a conversation engaging his partner to find out more about her and listening to her. When you’re just starting out, it’ll probably be more like 50-50 or 60-40, but you should gradually be paring down how much you talk about yourself with time, and focus more on talking about your partner, and sometimes about people in general. Sometimes, you won’t even talk about yourself at all, and that’s okay.
- Manage the conversational flow. Something that frustrated the hell out of me once I started deep diving and relating was that my conversations would get deeper and deeper and deeper, until eventually we went so deep that there would be this sudden shift, almost like the spell had broken, and I and the other person I was talking to would suddenly find ourselves stranded back on the shores of superficiality and neither of us knew how to get back to where we’d been before. It was like the whole conversation had been a dream, and we’d just woken up – then couldn’t fall back asleep again.
These days, I’ve taken to managing the flow better – I take things deep, but bring them back up again periodically with a little lighthearted teasing or a witty comment here or there, or pointing out that something in the conversation is silly or doesn’t make sense. I then take it back down deeper again. It ends up looking like this:
Person B: … and then I never heard from him again. He just disappeared. I felt awful for three months.
Person A: Wow, that’s terrible. [pause for maybe five seconds, let the dust settle from the deep emotions] So I guess you feel a lot better these days! [said with warmth and a smile]
Person B: Yeah, I do.
Person A: That’s the cool thing about bad, sad experiences – people are strong, and we bounce back. Even if it feels pretty bad for a while, it doesn’t stay feeling bad forever. We’d never make any progress that way.
Person B: You’re so right.
Person A: So after this guy pulled his disappearing act, what’d you do to get your life back in order?
Person B is sharing this very deep, emotionally powerful experience, but it reaches a conclusion. Person A brings her back up from that; he commiserates, then makes it light and airy again, like a breath of fresh air. He tells her she must be feeling a lot better now; she agrees. All that darkness she was feeling earlier fades away, and she feels good and warm in his company. He’s taken her down, but brought her back up again.
Remember that voice tone is very important here. You can use different tones, and sound cold and insensitive saying Person A’s lines with one, or warm and considerate saying them with another. Play around with your voice tones to get the right ones. Watch a lot of movies with strong, confident, charming characters, and learn to talk like they talk.
So Person A does a bit of inspirational talk, and then he goes back into the deep dive again, finding out more about Person B’s life’s trajectory and getting her talking about what she did after this experience. It’s natural to go back into it now that she’s come up for air; now they can go back down again for a little bit, before coming back up again later.
Managing the conversational flow like this does two things for you:
• It keeps things from getting so intense and heavy that people start feeling a need to break out of the oppressive intimacy of the conversation and free themselves, and
• It gives your conversation partner a shot of good feeling and reassurance and, most importantly, perspective, giving her the strength to continue through her story, whether it’s a happy memory she’s discussing or a painful one.
If you’ve ever seen the movie The NeverEnding Story, the feel of this movie is exactly the feel of what you should be going for in your management of the conversational flow. The story intensely sucks you in, at times feels overbearing, but then you get sucked out of it and everything is put back into perspective when Bastian closes the book and stops reading. He takes a break. Then he goes back into the book and we get sucked back in. That’s the feel of it.
- You must not judge. There is this social enforcing behavior we all tend to get instilled with very early on in life, and it’s called “judging.” We use it to put social pressure on others to conform to our views about what is correct behavior and avoid engaging in incorrect behavior. If someone engages in enough incorrect behavior, we judge them quite poorly, and effectively consider them out of our social class, clique, or tribe.
Here’s the thing: the more you judge, and the more harshly you judge, the more you limit your social potential. Almost everyone you meet is going to have things that clash with something or other about your own personal beliefs and values systems. If you take issue with people over that kind of thing – even if you just take issue inwardly, but try to be friendly outwardly – people will sense it; they sense the gulf between the two of you, and they close up.
No conversation. No connection. Just awkwardness, and a desire for the interaction to end as quickly as possible.
The conversationalist does not judge. He teaches himself not to judge on the inside as well as on the outside; he accepts that many people are different from him, but that different doesn’t equal bad, and he forces himself to stop having bad, negative, derogatory thoughts about others because he know it will cripple his ability to succeed socially.
Don’t judge. It cuts your legs out from the standpoint of connection-, friendship-, and relationship-building. People are infinitely more honest with you when they can tell they’re being accepted by you for whom they are, free of judgment. The sizeable boost in trust and depth of bonding with others that you gain from getting over any judgmental tendencies you have now is well worth the month or so of work you’ll put in of monitoring your thoughts and shutting down judgmental thoughts about other people to rewire your learned thought processes.
Judgment is learned, and it’s unlearned as well. I suggest you remain discriminating – certainly you will be choosy about having top quality people in your life – while simultaneously freeing yourself of the burden of being judgmental. In addition to opening up whole new social vistas to you, you will find you actually feel much better without a cluster of negative judgments running around in your head poisoning your thoughts.
- Be a lighthouse. I’m an Aquarius. That means that I have a great deal of empathy for other people, but also that I’m quite emotionally detached. I don’t get affected by things the way others do, but I care about them enough that I want to see them do well and succeed and prosper and feel good and confident.
If there is one thing that drives me nuts when it comes to conversationalists, it’s seeing a guy who’s good at conversing but who clearly doesn’t give a damn about the people he’s talking to. You know, the guy who’s focused more on himself and what he has to say than he is on the other person and couldn’t tell you how someone else is feeling to save his life.
I recommend walking a mental mile in the shoes of everyone you talk to. Put yourself in every person you meet’s position and ask yourself how you’d feel if you were them. It’s enlightening. And it also makes you realize how much people need you to be an uplifting, motivating, strong person for them.
I call this being a lighthouse. The lighthouse is the beacon on the rocks that guides ships to safe passage, no matter the weather conditions. It’s a sign of hope, and also one of strength; a solitary beam of light in the darkness. You should seek to provide hope, encouragement, strength, and high spirits to those you speak with. Be honest and realistic, of course; if someone proposes a business or relationship idea to you that you know will fail, for instance, tell them you have some fairly strong reservations about it, but give them much credit for being creative or hopeful, and perhaps suggest an alternative they might use.
Again, you must balance this; you don’t want to be so wildly optimistic that it’s patently unbelievable. You want to provide gentle, subtle guidance and support; not be crazy happy, but exude more of a calm, guiding confidence that the person you’re talking to will be okay no matter what path she chooses.
Training Yourself Up as a Conversationalist
Obviously, if you want to be good as a conversationalist, you’re going to need to go have a lot of conversations. Beyond that, there are a few other things I can recommend you do to get yourself started.
- Form a plan of attack. I recommend only working on one or two of the above points at a time. I listed seven of them – too many to work on at once. You don’t conquer the world by attacking the entire world; you conquer the world one country at a time. So it is with this – bite off one chunk at a time and go from there.
- Identify your own deficiencies in conversation to use as a starting point. If you have an awful time getting past small talk, start with that. Work on deep diving and see if you can get into some real conversation about real stuff. If you have the bad habit of talking too much about yourself, get better at turning the conversation back to the other person. If you find yourself saying or thinking negative things sometimes, focus on clearing judgmental beliefs out of your system and strive to be a lighthouse.
- Pay more attention to what people are telling you… and not telling you. If there are things about people you’d like to know, but don’t, find ways to start getting them to tell you that information. Usually you’ll start out rather clumsily, just asking for it; as you hone your skill, you become more and more adept in getting people telling you what you want to know. Eventually you can reach the point where people enjoy talking to you so much and become so eager to connect with you that if you simply bring them to a topic, they will proactively tell you the things you’re curious to know without you even needing to ask.
- Get more experiences. The more things you do, and the more things you get comfortable with, the better you’ll be able to relate to people. When I first started working on my skill as a conversationalist, I suddenly began taking on a variety of very different activities (international travel, language studies, social activities and mixers, sports, martial arts classes, dance classes, acting, modeling, photography) in part because they interested me, but also in part because I wanted to have these experiences to be able to relate to more people more easily. Most of them I didn’t spend a huge amount of time doing, but I’m now able to relate to anyone who talks to me about snowboarding, or traveling to Europe, or learning Spanish, or dancing salsa, or going to a photo shoot because I’ve done those things at least a little bit.
- Get talking (with new people). Meet new people, get into conversations. It’s different when you’re talking with classmates, or officemates, or family members, or old friends. You know them; you don’t have much work to do to get to know more about them. Meeting new people forces you to learn how to get to real conversation fast, because you don’t have a lot of time. Take too much time dancing around with small talk, and most people will start feeling uncomfortable (the result of lacking the formation of a connection or finding common ground fast enough) and leave. You meet a wider variety of people, with a wider variety of life experiences, and a wider variance of tolerances and conversationalist aptitudes in their own rights, so you are constantly having to adjust and make changes on the fly. This is hands down the best, most reliable, most effective way to get conversational abilities down; meeting lots of new people is a bit of a gauntlet, but it’s a gauntlet that will see you come out the other end much improved.
When should you start? Well, the cool thing about conversation is you’re always having it. So I recommend you begin training yourself up as a conversationalist the next time you have a conversation.
Get good at talking to people. It’s a game changer in pretty much every way;becoming a talented conversationalist is one of the most fundamental, significant ways you can improve yourself, period. So don’t put this one off until tomorrow – start improving the very next time you say “hi” to someone. It’s worth every ounce of the effort you put into it, and the payoffs will last you a lifetime.
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