One of the things that makes Michael Vassar an interesting person to be around is that he has an opinion about everything. If you locked him up in an empty room with grey walls, it would probably take the man about thirty seconds before he'd start analyzing the historical influence of the Enlightenment on the tradition of locking people up in empty rooms with grey walls.
Likewise, in the recent LW meetup, I noticed that I was naturally drawn to the people who most easily ended up talking about interesting things. I spent a while just listening to HughRistik's theories on the differences between men and women, for instance. There were a few occasions when I engaged in some small talk with new people, but not all of them took very long, as I failed to lead the conversation into territory where one of us would have plenty of opinions.
I have two major deficiencies in trying to mimic this behavior. One, I'm by nature more of a listener than speaker. I usually prefer to let other people talk so that I can just soak up the information being offered. Second, my native way of thought is closer to text than speech. At best, I can generate thoughts as fast as I can type. But in speech, I often have difficulty formulating my thoughts into coherent sentences fast enough and frequently hesitate.
Both of these problems are solvable by having a sufficiently well built-up storage of cached thoughts that I don't need to generate everything in real time. On the occasions when a conversations happens to drift into a topic I'm sufficiently familiar with, I'm often able to overcome the limitations and contribute meaningfully to the discussion. This implies two things. First, that I need to generate cached thoughts in more subjects than I currently have. Seconds, that I need an ability to more reliably steer conversation into subjects that I actually do have cached thoughts about.
Below is a preliminary "conversational map" I generated as an exercise. The top three subjects - the weather, the other person's background (job and education), people's hobbies - are classical small talk subjects. Below them are a bunch of subjects that I feel like I can spend at least a while talking about, and possible paths leading from one subject to another. My goal in generating the map is to create a huge web of interesting subjects, so that I can use the small talk openings to bootstrap the conversation into basically anything I happen to be interested in.
This map is still pretty small, but it can be expanded to an arbitrary degree. (This is also one of the times when I wish my netbook had a bigger screen.) I thought that I didn't have very many things that I could easily talk with people about, but once I started explicitly brainstorming for them, I realized that there were a lot of those.
My intention is to spend a while generating conversational charts like this and then spend some time fleshing out the actual transitions between subjects. The benefit from this process should be two-fold. Practice in creating transitions between subjects will make it easier to generate such transitions in real time conversations. And if I can't actually come up with anything in real time, I can fall back to the cache of transitions and subjects that I've built up.
Naturally, the process needs to be guided by what the other person shows an interest in. If they show no interest in some subject I mention, it's time to move the topic to another cluster. Many of the subjects in this chart are also pretty inflammable: there are environments where pretty much everything in the politics cluster should probably be kept off-limits, for instance. Exercise your common sense when building and using your own conversational charts.
(Thanks to Justin Shovelain for mentioning that Michael Vassar seems to have a big huge conversational web that all his discussions take place in. That notion was one of the original sources for this idea.)
Questions are great, but they have certain limitations:
If you are beginning a conversation with some who you don't know well, they may not give you very extensive or useful answers to your questions.
You can only ask so many questions in a row before you are interviewing them. Worse, it looks low status.
For people who over-rely on questions, they often ask a question, get a short or one-word answer, and then ask another questions, getting the same type of answer. After about 3 or 4 of these, the conversation is dead in the water.
The solution is to limit the amount of questions you ask until the other person becomes invested in the conversation enough to give you real answers. The PUA Juggler advises asking less questions and making more statements. Making statements engages the other person, and unlike questions, don't require the other person to reciprocate, avoiding the interviewing, chasing, or badgering dynamics that questions can cause. Making statements gives the other person information about the kind of person you are, which helps them decide if they want to open up to you. Of course, statements still need to be related someone to the current conversational context, or the other person will be wondering, "why are you telling me this?"
Here is an example of how you can get stuck in a rut with questions. This is a Standard College Conversation:
Student1: Hey, how's it going?
Student2: Good... you?
Student1: Pretty good... how was your weekend?
Student2: It was good.
Student1: Cool... where are you living nowadays?
Student2: Dorm Blah Blah Blah.
Student1: Nice, how is it there?
Student2: It's good...
A surprising amount of conversations go like this. Student2 is necessarily trying to be unhelpful; he just isn't yet invested in the conversation. After each of Student1's questions fail to hook Student2 into the conversation, he asks another questions which gets a similar response.
A better approach is for Student1 to start making some statements. Making statements gives him a lot more opportunities to hook Student2. Here are some examples:
Student1: Hey, how's it going?
Student2: Good... you?
Student1: Great! You'll never guess what happened to me today...
Now Student2 is engaged. Instead of firing back with another question, Student1 starts talking about what he was up to (if you ask a question and get a noncommittal answer, you can often answer your own question). In case, "you'll never guess what happened to me today" is a bit too much of a gimmick, here is another way:
Student1: Hey, how's it going?
Student2: Good... you?
Student1: Great! I've been having a crazy day... [describes what happened]
In the original conversation, Student1 only had 4 possible hooks into a conversation: one for each question he asked. In this example, telling an anecdote about what happened during his will give him a lot more hooks that will inspire a response from Student2 to either ask questions back, or talk more about his own day.
Any of the questions that Student1 asks in the conversation could be turned into an opportunity to answer it himself, giving him the opportunity to tell a story about what is going on in his life:
Student1: Hey, how's it going?
Student2: Good... you?
Student1: Pretty good... how was your weekend?
Student2: Awesome, I went to this party / book club, and [describes what happened]...
Student1: Hey, how's it going?
Student2: Good... you?
Student1: Pretty good... how was your weekend?
Student2: It was good.
Student1: Cool... where are you living nowadays?
Student2: Gamma Gamma Gamma.
Student1: Cool, I'm in Kappa Kappa Kappa. It's a funny place... [starts talking about something that recently happened at his dorm]
Once someone gets invested in a conversation and engaged, then you can start asking questions and getting in-depth answers. Sometimes a question alone will engage them, but if it doesn't, you can fall back on making statements (and answer your questions yourself) until the other person is sufficiently engaged.
If someone only gives me one-word answers, that means that they do not want to talk to me (but are too polite to tell me to get lost), and if I choose to disregard that, I don't get to complain when I get labelled and treated as a creep.