Questions to Ask Anyone in Conversation
Twenty general questions for getting past small talk with almost anyone, ordered from easy openers you can use with a stranger to the ones that only work once a conversation has warmed up.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What have you been up to lately, apart from work?
It gives an easy exit from the job question without demanding anything personal. If someone struggles to answer, that itself is worth a gentle follow-up about how busy things have been.
- 2
What is taking up most of your time at the moment?
Better than asking what someone does, because it catches the new baby, the house move or the course they are halfway through. It also lets a person who dislikes their job talk about something else.
- 3
Is there something you are looking forward to in the next month or two?
Near-future plans are easier to talk about than ambitions and usually produce a concrete story. A blank answer is often a sign someone is having a flat spell, which is useful to know.
- 4
What did you get into recently that you did not expect to like?
The surprise framing gets past the rehearsed list of hobbies people give at parties. Answers tend to be slightly embarrassing and therefore genuinely revealing.
- 5
Where did you grow up, and would you go back?
The second half turns a routine question into a real one, and the answer covers family, class and belonging without asking about any of them directly. Listen for whether they say back to the place or back to the people.
- 6
What is the last thing you recommended to someone?
Recommendations show taste and generosity at once, and they are easier to produce than favourites. It also gives you something specific to follow up on later.
- 7
What do you know a surprising amount about?
This invites expertise rather than credentials, so you get the birdwatching, the tram network or the obscure sport. Most people enjoy this question because nobody asks it.
- 8
What is something you have changed your mind about?
It shows how someone handles being wrong, which tells you more than their current opinions do. Vague answers usually mean they are giving you a safe one.
- 9
What did you want to be when you were twelve?
Twelve is old enough to have a real answer and young enough to be free of strategy. The gap between then and now is where the interesting part sits.
- 10
Who has taught you the most, and what was the lesson?
The named person matters less than what they were teaching, and it often turns out to be a grandparent or an early boss. Asking for the lesson stops it becoming a list of names.
- 11
What is the best decision you made in the last few years?
People are more comfortable with this than with the worst one, and it still gets at values and courage. Notice whether the decision was about work or about a person.
- 12
What is a small thing that reliably improves your day?
The answers are specific and cheap, and they tell you what someone's ordinary life looks like. It is also one of the few questions where the answer is immediately useful to you.
- 13
What do you find easy that other people seem to find hard?
This is a strengths question that avoids the awkwardness of asking someone to praise themselves. The answer often points to work they should be doing more of.
- 14
What is something you have stopped doing that you do not miss?
Quitting stories are underused and usually funnier and more honest than achievement stories. They also reveal what someone has learned to protect.
- 15
What would you spend more time on if the money were the same?
A better version of asking what someone would do with a windfall, because it isolates preference from wealth. Very short answers here often mean someone has not thought about it in years.
- 16
What is a belief you hold that most people around you do not?
It gives permission to be interesting rather than agreeable. Be ready to disagree without correcting them, or do not ask it.
- 17
What has been harder than you expected this year?
Naming difficulty is a real disclosure, so only ask once the conversation has warmed up. Match whatever depth they offer instead of pushing for more.
- 18
What are you worried about that you do not talk about much?
This is a late-conversation question and it needs you to be ready to answer it yourself. A deflection is a perfectly acceptable answer and should be let go without comment.
- 19
What do people usually get wrong about you?
The answer is often something someone has wanted to say for a long time. Do not reassure them that nobody thinks that, because it closes the topic.
- 20
What do you hope is different about your life in five years?
Hope is easier to admit than a plan, so this gets a truer answer than asking about goals. The part they mention first is usually the one that matters most.
Getting Past Small Talk
Practical guidance for the conversation itself.
How to Actually Use a List Like This
How to Actually Use a List Like This
One Question, Then Follow the Answer
The value is almost never in the question, it is in the second and third thing you ask about what they said. A person who runs down a list is conducting an interview, and it feels like one.
Answer It Yourself First When It Is Personal
Going first sets the depth and proves you are willing to spend what you are asking them to spend. Keep your own answer short so it reads as an offer rather than a monologue.
Work Up, Not Straight In
The questions near the end of this list will land badly in the first five minutes with a stranger. Warm ground is recent life and enthusiasms, and worry and regret come much later or not at all.
Let Silence Do Some Work
Most people fill a three second pause with a new question and lose the better answer that was coming. Count to five before you speak again.
What Makes These Fall Flat
What Makes These Fall Flat
Asking Something You Do Not Want the Answer To
If you ask what someone is worried about and then change the subject, you have made things worse than if you had discussed the weather. Only open a door you are willing to walk through.
Competing With the Answer
Following someone's story with a bigger version of your own ends the exchange. Ask one question about their story before you offer any of yours.
Deep Questions as a Personality
Skipping past ordinary conversation to demand significance reads as intense rather than interested. Small talk is the ramp, not the enemy.
Asking in Front of an Audience
Anything personal becomes a performance at a table of six, especially for the person who has to answer. Save those for a walk, a car, or a corner of the room.
Adapting to the Situation
Adapting to the Situation
- With a stranger at an event, stay in the first eight questions and stop while it is still going well.
- With a colleague, keep to what they are working on, what they are good at, and what they have changed their mind about.
- On a long drive or a walk, the middle of the list works because nobody has to make eye contact.
- With someone you have known for years, skip the openers and go to what has been harder than expected.
- Over a meal with family, one question asked of everyone in turn works better than a real conversation with one person.
- If someone gives a one word answer twice, they are telling you something. Change register rather than trying a third question.