In most groups, there are only a few people who are good at both starting and continuing on a conversation. Usually, this stems from an ability to ask others questions. Asking questions helps those who normally wouldn’t talk much to open up more because you are showing interest in their lives.

It can sometimes be hard to come up with questions on the fly. There are some of the big ones that almost everyone asks. “What do you do,” “Where are you from,” etc. These are easy go to’s because it causes interest and has the potential to develop common interests.

For example, finding out that someone is from a place that your best friend is from, so you mention this and tell them their name and ask if they knew each other.

The crux comes when you get through these basic questions and you can’t think of any more follow-up questions. What do you do now? You’ve pretended to be interested for several questions, but you never were actually interested, so now that it comes time to ask genuine questions, you’re at a loss.

The trick is not much of a trick at all. It’s to be genuinely interested in what they’re saying. Of the people I meet, about 1 in 25 seem to have this skill. Most people I talk to, I immediately get the feeling that they are only interested in conversation with me to

  1. Get to share about themselves
  2. Not feel awkward staring at each other
  3. Make me feel interested while the search for a better person to have a conversation with

Of course a part of this is my over analyzation, but the truth is that most people, included myself, are not usually that interested in other people. Not everyone picks this up, but it becomes apparent when the questions about who you are stop after only a couple follow-up questions.

Humans are so unique that one couldn’t help to get to know everything about another in an entire lifetime, yet we get through 4 or 5 questions with someone and we hit a roadblock feeling like there aren’t any other questions to ask.

This is because when we meet others, we put walls up at certain levels. Or we assume that others have walls up that won’t allow us to get past a certain level.

If I were to think of a bad analogy, it might be this:

Imagine every person is a castle with a moat around them. Between the castle and the moat, there is a wall. An outsider can never go past the wall, they can only go up to it. Once next to it, they can slowly push the wall in toward the castle after time.

What happens when we first meet someone is we jump over the moat, but people have their wall so close to the moat, that we don’t have any footing once we’re past the moat, so we have to jump back to our side of the moat before we can get any footing.

These are the “where are you from, what do you do” then silence…. Conversations. There’s nothing else to ask it seems. The wall is too close to the moat to get any traction.

The truth of the matter is that we imagine a wall after the moat, but very few people actually keep their wall that close to their moat. It may be shocking for them if you jump past their moat and immediately start running toward the castle, but a jump across and a quick walk towards is actually comforting.

…I may be too deep into the analogy, but the idea is that by meeting someone and genuinely asking questions about them and asking questions about the answers they’ve given you, you really start to move closer to getting to know the real them (the castle). It will take years to get to a clear picture of the castle, but the more you walk close to the wall, and sometimes push it a little bit, the more you get a clearer picture, and the more you enjoy the space there because you’ve given yourself so much room to get to know them.

As soon as you get past the silly surface-level stuff, you have a whole heap of things to talk about and ask about.

So many people never get here because they make fake walls for other people, but almost everyone is open for deeper levels of conversation. They just don’t know until you ask them the questions.