This week I've been thinking about when I last had a "deep" conversation.

You know the type of discussion where you talk about more than just what's happening in life, and more about what those things mean. For example, chats on religion, your plan in life, philosophical ideas, moral issues, etc.

In my case, it used to happen a lot at university, and not much more since – I guess that's natural since you have more time with your friends then and there's less small talk to be made. But since I love these kinds of chats, I'm now consciously trying to "engineer" them in my daily (busy!) life where I catch up with friends much less frequently.

If you're also keen to spend less time on the same boring "how's work going" chitchat and more time on deeper topics, then there are 3 things I'm doing now to help spark deeper conversations that you might find helpful.

1. Recognise and avoid small talk

Unfortunately, the default mode is often small talk. This is like the lava floor you are trying to avoid. "How're you doing" is OK. "How's work / family / day-to-day going" is a sign to move on. Think of every minute as precious – and so every minute spent on extended small talk is a minute of your life you're never getting back and one you likely won't remember.

2. Ask provocative questions

As with most things you'll do in life, you can prepare for a deep conversation (you're already doing so by making it this far!). I find that it helps to have some provocative questions in mind that you can ask. These may be questions that are a bit personal, or questions that force someone to express an opinion on an issue that matters. For example:

  • What keeps you up at night? – personal question
  • Why do you believe in your religion? – personal question / force an opinion
  • Are people inherently good or evil? – force an opinion
  • What's the most controversial opinion you have? – force an opinion
  • ...

You're not looking for a yes / no answer. The point is to spark conversation on a topic where you're not discussing your day-to-day but your opinions and feelings. What can you add to the list?

3. Invest time + create the right environment

The best conversations take time (and indeed you'll want them to if you're having fun!). If you're just doing a catch-up over a meal, you gotta work with what you have. But if you plan a weekend away with your friends, that sets a different tone entirely.


Deep conversations do come organically – doesn't mean you can't nudge the process along. I think if that's something you enjoy, it's totally worth being more intentional about it by steering the conversation in the right direction.

Do let me know if this is something you think about, or if you have any other ideas to add!