Everyone is interesting

I have a confession to make.

I love it when I come across someone who’s deeply interested in something, and can talk engagingly about it for hours on end. Give me someone who can ramble passionately about 18th-century fencing manuals, and I’m all ears. I’m obsessed with people who obsess. I don’t care what it is: rocket science, extreme ironing, or a long-held fascination with stamps from the 1980s.

What’s compelling is that they’re knowledgeable and that they care.

When you get someone talking about a topic in this way you can really feel the tempo of the conversation change. I’ve had plenty of conversations where every response I got back was a one-word answer - then one question about a specific topic changed everything. Suddenly it was like speaking to a different person.

So the heart of today’s post is this: everyone is interesting, you just have to ask the right questions.

Trial and error

I am a profoundly anti-social person by nature. But various life choices have forced me out of this insular shell. It turns out, starting a company means getting comfortable approaching strangers and striking up a conversation. Who’d have thought it?

Often, I’ve found myself needing to interact with people I’ve only just met. Sometimes this is one-to-one, sometimes it’s a large group.

After repeatedly forcing myself to walk up and make introductions to individuals and groups at various conferences and gaming industry events, it rapidly became clear that things get awkward very quickly if you’re not someone with a wee bit of charisma. This is doubly true if those you’re approaching aren’t all that socially fluent themselves.

Several years of trial and error have led me to a few simple tricks for keeping conversation engaging in those first few moments¹.

Starting on the right foot

I took a very measured, strategic approach towards interacting with people at conferences². It’s not something I’d do in normal social situations, but this was different - failing to hone my social skills could be the difference between getting a publishing contract or not.

Because of this, I found myself keenly observing how people interacted with me. Most default into one of a few different buckets when interacting with others:

• Relaters - Those that do this well share stories of their own as a way to relate to your experiences and demonstrate empathy. If done badly, this can come across as someone constantly trying to one-up you.
• Questioners - When done well, the person on the receiving end of this style of conversation feels as though they’re being deeply listened to and engaged with. Done badly, it can feel like being interrogated by a never-ending fire hose of questions.
• In-jokers - This is more common in groups of close friends, but the entire conversation centres around shared jokes and references, or reminiscing about times past. If you’re in the clique then it really helps cement existing bonds. If you’re not, it can feel rather exclusionary.
• Monologuers - If someone’s particularly engaging or charismatic, they can hold the attention of those around them with a series of engaging anecdotes and jokes. More often than not though, someone talking in this style leaves others feeling bored and ignored.
• Gossipers - These kind of socialisers centre their talk about sharing stories about others. If done in good faith, this usually feels like you’re being let in on a secret. It’s easy for this kind of conversation to turn mean-spirited and nasty though.

There are plenty more styles, but these are some of the common ones I’ve observed. It’s usually fairly easy to notice quickly how a group relates to one another, such that when you join in with the conversation, you can mirror that style. It’s a great way to leave a good early impression and it helps dilute some of the discomfort and clunkiness that naturally arises from inserting yourself into a conversation.

However, if you’re dealing with an individual it can be harder to read things quickly. As a general rule of thumb, you want to match the energy of the other person early on. Someone that’s very quiet and withdrawn will likely feel uncomfortable if you enter a conversation full-force - no matter how big your desire to fill the empty spaces in the conversation³.

Leading and following

Once you’re comfortably into a conversation, you can begin to have more agency as to its direction. Different groups and situations work better with different approaches, but for the purposes of this blog let’s speak about one in particular: asking good questions.

I truly believe that every single person out there is interesting to speak to - it’s just a case of getting them onto the right topic.

So the key question is, how do we do that?

There are two main things to focus on. The first and most important thing is to listen to where the other person focuses their attention. Whenever anyone is talking, they are always (consciously or unconsciously) trying to nudge it towards a topic that they want to speak about. This will surface in their choice of words and in how much of what they say is dedicated to a given topic. When trying to find a person’s areas of interest, you’re looking for which things they tend to repeatedly bring up. When someone’s doing this it usually means that they have something to say about it, but they’ve just not hit on the right way to do so without things feeling forced.

That brings us neatly to the second thing - asking the right questions. Early on you’ll want to use very open questions⁴ as a way to give the other person plenty of scope to start mentioning things they might be interested in. Once you spot a recurring theme, more specific, closed questions give the other person a chance to open up a little more. I find two things really important here. Firstly, try to match some of the words they use. Provided you’re not wholesale repeating what they said, this demonstrates that you’re engaged and actively listening. Secondly, if you’re relatively confident you’ve found something they truly care about, it helps to be openly excited about it. Phrases like “I’ve always been super interested in ‘X’! Can you tell me a bit about it?” go a long way to giving people the comfort to open up, and also shows that you’re not just making small talk.

As mentioned earlier, this social style can sometimes feel like an interrogation. Because of this, it’s vital that you don’t just fire question after question - particularly if the person you’re chatting with is giving very short responses and not asking you any questions back. You can mitigate this by dropping in anecdotes that relate to whatever it is you’ve been speaking about here and there.

Striking gold

There is an endless amount of nuance and chaos to understanding social interaction. People are varied, unpredictable, wonderful and frustrating. It feels to me like there is an endless depth of things to learn. Often that which we know intuitively about one another can be very hard to express clearly.

Throughout all of my interactions though, there is one thing that has held true: if by the end of a conversation the other person is doing most of the talking, I know that things have gone well.

If you’re doing none of the talking and all of the listening I know things can seem one-sided. But there’s a brilliant feeling when you start talking to someone new, and by the time you’re done, it’s hard to stop them speaking about a subject they’re clearly passionate about. You learn so many interesting, unexpected things.

Everyone’s got a story worth telling. You just have to be curious enough to find it.