How to Ask Deeper Questions

First shared on Substack Part 1 / Part 2.

These questions have worked well for me as I do Author Interviews, but also just in my regular life and wanting to get to know people better. I don’t necessarily think these questions are deep, but I think they can bring out deeper conversations if people want to pursue them.

1. Ask what people do, but also ask why they do it, or what is the motivation behind it.

For instance, ask someone what they do for work, and then ask why they chose that line of work or what got them into it in the first place.

2. Ask how things make people feel.

A lot of times you can talk about a topic or event, but to get to know a person, you want to know the feelings and emotions. For example, if a person is facing a new project at work — does it make them excited, scared, optimistic, or anxious?

3. Ask about family and friends.

Our families and friends, and how we feel or relate to them, tell us a lot about ourselves. For instance, are you married or single? Dating? Kids or no kids, how many or why not? Who do you hang out with and what types of activities do you like to do?

4. Ask about church and hobbies.

For some, talking about work may be mundane. Asking about church or hobbies gives people the opportunity to discuss spiritual matters and personal passions.

In a world of Artificial Intelligence, I have found true human conversation to be a common grace. And as we connect and draw close to each other, we reflect and display the glory of God.