Deep Questions
Ask how people feel about their life, not the facts of their life.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 3
- Confidence
- 92%
Deep questions are questions about someone's values, beliefs, or experiences, and they are far easier to ask than people assume. Instead of asking about the facts of someone's life, you ask how they feel about it, which invites them to share something meaningful and slightly vulnerable. When you reciprocate with your own vulnerability, both brains become wired to trust each other more. Super communicators ask ten to twenty times as many questions as the average person, and any piece of small talk can be converted into deep talk with one follow-up.
Origin
Duhigg studied super communicators and found their first consistent habit was asking far more questions than average. Researcher Nicholas Epley at the University of Chicago demonstrated the power by setting himself the goal of having a deep conversation within five minutes of boarding a bus — strangers ended up sharing their marriages, homes, and life stories because people fundamentally want to share.
Core principles
- 01A deep question asks about someone's values, beliefs, or experiences.
- 02Ask how people feel about their life rather than the facts of their life.
- 03Deep questions invite people to expose a small, safe vulnerability.
- 04When you reciprocate that vulnerability, brains are hardwired to trust each other more.
- 05Any small talk can be turned into deep talk with a single follow-up question.
- 06The simplest deep question is 'What do you make of that?'
How to run it
- 1
Swap facts for feelings
Turn a factual question into an emotional one — instead of 'Where do you live?' ask 'What do you love about where you live?'
Pro tip A feeling question exposes values (community, politeness, choice) that give you real common ground to reciprocate.
Watch out Fact questions like 'Where do you work?' are conversational dead ends that are hard to follow up on.
- 2
Ask a follow-up to go deeper
After any answer, ask why they chose it or what they love about it to invite them to share beliefs and experiences.
Pro tip 'What do you make of that?' is the most reliable all-purpose deep question.
- 3
Reciprocate the vulnerability
When they share something personal, answer the same question about yourself so it feels mutual, not like an interrogation.
Watch out Asking question after question without sharing yourself makes people feel interrogated rather than connected.
In the wild
Asking 'Where do you live?' gets a dead-end 'Santa Cruz.' Asking 'What do you love about where you live?' gets 'Everyone's focused on community, people let me into traffic, no one honks' — revealing that the person values community and politeness and chose to live there.
→ The richer answer gives natural common ground and makes it easy to reciprocate with your own reasons.
University of Chicago researcher Nicholas Epley sets a goal of having one deep conversation within five minutes of getting on a bus. He asks a stranger not just what they do but whether they like it and how they chose the path.
→ Within five minutes strangers are talking about their marriages, homes, and the countries they came from.
Common mistakes
Staying on the facts
Asking only about facts of someone's life produces dead ends with nothing to follow up on and no emotional hook.
Interrogating instead of sharing
Firing off questions without answering them yourself makes the exchange feel like an interview and kills the sense of building something together.
Is it for you?
Best for
Networking, first meetings, and anyone who wants to move past shallow small talk quickly.
Not ideal for
Situations where the other person genuinely wants to be interviewed for information rather than to connect.
From the transcript
“a deep question is something asks about someone's values beliefs or experiences”
“don't ask someone about the facts of their life ask them how they feel about their life”
“anytime you're having small talk you can make it deep talk just by asking a question”
From the episode
Charles Duhigg: Become a Superconnector, How to Build Lasting Relationships That Matter
Charles Duhigg