How to improve your questioning: 3 tips for the curious but shy, from someone who used to go red when talking to strangers.

I’m a naturally shy person.

Despite any personality test I take indicating I’m just on the side of extroverted (which actually makes me an ambivert, so I’m told), my default inclination in social situations is to sit quietly and listen to other people.

But I often leave events wishing I had asked more questions.

Over the past seven years of running social events I’ve been forced to take the lead in many conversations, and continue to refine my approach to questioning.

Here are three tips I’ve found the most helpful:

1. Double click on any word or phrase to go deeper.

We end up asking basic, mundane questions because it’s all we can think of in the few seconds we have when we realise a person is about to stop talking.

A more interesting way to keep the conversation flowing is to listen out for unexpected phrases or descriptions, and ask them to expand on that idea.

2. Pull from adjacent topics to unlock broader questions.

We all get into conversations about subjects we have little knowledge of.

For me, I’m completely out of my depth talking to anyone about history. I know lots of important things happened, but I struggle to remember in what order and who was involved.

But I do understand the basics of politics and economics. So when I find myself in a historical conversation that leaves me feeling like a complete idiot with nothing to add, I just think about questions that could relate to the politics or economics of the period and bring them into the conversation.

3. Keep a list of interesting questions in your phone.

I’ve been collecting questions in my notes app since 2017. I have hundreds of them. I steal them from podcasts, from blog posts, from documentaries.

Before social events I often look through them and decide on three I want to get into a conversation that night. The challenge makes it fun and takes the pressure off coming up with new questions on the spot.

This post was created with Typeshare