How to be interesting

Sonnie Bailey

8 November 2019

I’m not the most socially skilled person in the world.

But I’m a LOT better than I used to be. Although there are some situations where I’m still not good, there are some social situations where I’m above average.

In other words: I’ve been a noddy, I’m still sometimes a noddy, but I’m not always a noddy.

In this article I want to share an exercise I often go through before I enter into a social situation which:

(a) gives me confidence and makes me act more sociable, and

(b) gives me more social ammo and enables me to be more engaging.

Conversational caching

I call it “conversational caching”.

When I mention it to some people, they think it’s weird.

But it works for me, so take or leave (or adapt) to suit yourself. You do you.

The term “caching” is apt because it’s a bit like taking thoughts and ideas that are already in my mind (my hard drive, so to speak), and it brings them to the fore and more readily accessible (my ram). It’s similar to what a computer does when it caches.

Before I enter into a social situation, I sit down and brainstorm things to talk about, and ask.

This includes social situations like parties, conferences, meetings, and even one-on-one dates with my wife. (Yep.)

Here are some of the things that I look at when I brainstorm, or load my “conversational cache”, with some current examples.

  • I look at my calendar. In particular I look at the last couple of weeks and mine it for anything interesting I’ve done. I look at the next few weeks (and sometimes skim through the next few months) to look at interesting things I’m about to do – or things that might be worth asking about. I also consider gaps in my calendar, where I might have room to make commitments – for example, to suggest catching up with other people at another time in the future.

Very often, before I do this I’m tempted to think I live a boring life. But afterwards, I’m almost always astonished about how I’m living the full catastrophe of a rich life.

  • I look at my Kindle and look at books I’m in the middle of, or that I’ve recently finished, or are sticking with me. For instance, in terms of non-fiction I’ve recently finished Range: Why Generalists Triumph in a Specialised World by David Epstein, and I’m reading Scarcity: Why Having Too Little Means So Much by Eldar Shafir and Sendhil Mullainathan and The Power of Moments by the Heath brothers.  In terms of fiction I’ve just finished reading Vicious and its sequel Vengeful by VE Schwab and Sweet Sorrow by David Nicholls. Less recently I’ve recently read Dark Matter and Recursion by Blake Crouch, but both books have stuck with me.

I also like asking people what they’re reading or what they’ve recently read. Sometimes I ask if they’ve read or come across certain books I’m thinking of reading next. At the moment, for instance, I’m wondering about whether to plough time and money into Michael Lewis’ The Fifth Risk and John Kay’s Obliquity. I’m also thinking of whether to read Wool by Hugh Howley.

  • I go through recent articles I’ve added or favourited on Pocket, my read-it-later app of choice. I may also look at my Twitter account to remind myself whether I’ve linked to any good articles recently.
  • I hop onto this blog and remind myself what I’ve published recently. I also look at articles that are “on deck” – that are in various states of readiness for future articles.
  • Lately I’ve been brainstorming the last few OUTRAGEOUS things that Donald Trump has done or said.
  • I brainstorm about things that I’m thinking about. Sometimes it might relate to work – high-level thoughts that might influence advice I’m giving (although I NEVER share anything that might even be close to identifying clients), or thoughts about my business where I want some feedback. I usually have one or two things that I’ve been thinking about, which I’m not sure whether I have a strong reason for believing, or whether I’m rationalising: I often ask people to be a devil’s advocate.
  • If I think I’m going to be chatting with specific people, I try to remember our last conversation(s) and what has been going on in their lives. This usually gives me questions to ask and additional things to discuss.
  • I brainstorm movies, TV shows, Youtube clips, and music I’ve been watching and/or listening to. In recent months I’ve been recommending the Happy Death Day movies and the Future Man TV show. The last movie I saw at the movies was Once Upon a Time in Hollywood and I have plenty to say about that. I’ve also got plenty to say about the movie Yesterday. My wife and I are enjoying The Boys and we’re excited that The Good Place has returned. When it comes to music… there’s nothing else but Taylor Swift’s new album Lover. (Although asking people “what’s your favourite song on the new Taylor Swift album” isn’t proving to be a good conversational gambit.)

My topics are fairly media-heavy and tend to be on the abstract side. Yours might be more events or experience or story-driven or influenced by conversations you’ve had and social dynamics you’ve observed (including but not limited to gossip!). Copy and paste what you want!

On top of this, I also have a list on my phone which includes a series of evergreen conversational gambits (questions and topics), and really bad taste jokes, to bring out when the moment demands.

This might seem like a lot of work. But it’s not really. I can do this all really quickly (~5 minutes at a push) and it’s a terrific investment of time.

If I have the time and want to feel a little more confident (especially if it’s a situation where I’m likely to not know many people) I can spend more time.

And then… forget it all!

And then… I forget it all. Quite often I may only use a small amount of what I brainstormed. Sometimes, I don’t bring anything up.

And that’s fine; the purpose isn’t to rabbit off a bunch of pre-planned conversation points. It’s often to create segues and introduce topics and questions for others to jump on board.

Comfort and confidence makes almost everyone more interesting

The point is to be prepared. The topics are up my sleeve and they’re in mind in a way they wouldn’t otherwise be. These topics and questions aren’t just in my hard drive, but they’re in my ram/working memory and are easily accessible.

Even if I don’t use any of these topics, this exercise provides another important benefit. It gives me a higher degree of comfort and confidence in the social situation. Which as someone who has historically not been the most socially skilled person in the world, is an amazing benefit.

In the lead-up to an event, it’s also much better to spend the time focusing and being productive than spending it ruminating and feeling anxious.

By being in your own head beforehand, it gives you more space to be present in the moment, allowing you to focus on your conversational partners, which in turn provides you with an opportunity to draw out more comfort and confidence in them as well.

The best way to be interesting is to be interested

The best way to come up with interesting topics to discuss, and questions to ask, is to be interested in a lot of things. I think of knowledge and interests like velcro: the more you know, the stickier your knowledge and interests become, making almost anything useful and interesting.

And yes: despite everything above, the best way to be interesting to other people is to be interested in other people.  Good conversations, like good relationships, are team sports.

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