“Going deep”

Whenever we’re with friends or new acquaintances and the conversation is getting a little bit stale/whiney/gossipy/surface level, I have a habit of bringing out my secret weapon: a list of questions I’ve collated from various websites and resources, which are intended to both reactivate the chat and “go deep” at the same time.

I don’t even bother with segues like “Hmmm, well, speaking of death…”: I just pull out my phone and shriek, “Hey! I have a bunch of questions that are really fun to answer – Tim Ferriss uses a bunch of them in the ‘quickfire’ round of his podcast interviews. Wanna try them out? Here’s one to get us all started: ‘What purchase of $100 or less has most positively impacted your life in the last six months?'”

Their eyes light up, they tell us all about the $15 slipper socks (OK that was Rob), or the $20 waterproof Bluetooth speaker (aaand that one’s me) they just bought, and we’re officially off to a great start.

Gradually, the questions get deeper:

  • What topic would you speak about if you were asked to give a TED talk on something outside of your main area of expertise?
  • What is the worst advice you see or hear being dispensed in your world?
  • What strange habit do you have?
  • If you could spend an hour doing anything, what would it be?
  • What have you changed your mind about in the last few years? Why?
  • What scares you the most about the future?
  • Do you have a secret hunch about how you will die?

OK, so admittedly we don’t tend to go that deep with most people. Usually, we’ll all take it in turns to pick a question from the list on my phone, and most of the time we’ll stick to the easier (but still mega interesting) ones.

It’s been a fantastic way to quit with the talk about food, TV shows and other people, and focus more on getting to know each other properly. There’s a chance we’ve freaked out a fair few friends along the way, but I like to think the success-to-WTF ratio is working pretty well in our favour.

If you want to see my humongous list of questions, they’ll all here.