3 conversation topics that help you know someone better

4 days ago

4 min read

Ask about a moment, a choice, or something they are looking forward to.

The question sounded better in your head. Out loud, it sounded like you were conducting an interview.

That can happen when you want to know someone better and try to make the next question do all the work. Suddenly you are both searching for the right answer instead of having a conversation.

Small talk was not the problem. It gave you a beginning. The next question needs to leave the other person room, not demand that they become fascinating on cue.

You do not need a question that reveals someone's whole life. You need something they can answer in their own way, and enough interest to follow the answer rather than hurry toward your next prompt.

Here are three directions worth trying: stories, values, and the future. They are openings, not a method for decoding people. Someone may offer a funny detail, a thoughtful answer, or not much at all. Let that be their choice.

1. Stories: ask about something that happened

"What was it like?" can be a better question than "Where are you from?"

The first leaves room for a remembered place, an ordinary routine, or a detail the person still loves. It does not require the story to be dramatic.

You might ask:

What's a place you remember especially well?
How did you get into that hobby?
What's a small decision that led somewhere unexpected?

These questions offer something particular to talk about. They work best when you ask because the answer interests you, not because you need to steer the conversation somewhere profound.

Listen for the detail that makes you curious. The friend who persuaded them to go. The first disastrous attempt. The reason they kept trying. A follow-up drawn from the answer usually feels less like an interview than a second question drawn from a list.

Do not assume an unfamiliar background needs explaining, or press for a painful part of the story. The person owns both what happened and what they want to tell you about it.

2. Values: ask what matters inside a choice

Values can sound abstract until someone describes what they chose.

An ordinary decision about a weekend, a job, or how to spend an hour can reveal what they are trying to protect. Not everything has to become a debate about principles.

Try:

What's something you've made more room for lately?
What makes a day feel well spent to you?
What's a piece of advice you used to follow that no longer fits?

You may hear an answer you do not share. That is not necessarily a problem to solve.

Ask what led them there before deciding what it says about them. People can hold conflicting priorities, change their minds, or be in the middle of working something out. One answer is not a permanent character assessment.

And offer something of yourself, too. Getting to know someone is not collecting their answers while keeping yours safely out of sight.

3. The future: ask what they are looking toward

"What are you excited about?" leaves more room than "What's your five-year plan?"

An answer might be a project, a trip, a person they will see, or a quieter week. The future does not have to be ambitious to be interesting.

You could ask:

What's something you'd like to try, even if you're not good at it yet?
Is there anything you're looking forward to this month?
What's an idea you keep returning to?

Let an unfinished idea stay unfinished. Someone telling you about a possibility is not automatically asking for a strategy, a contact, or a reason it will not work.

If you want to offer help, check first. Sometimes the conversation itself is what they wanted.

Someone may not feel hopeful just now. They do not owe you an exciting future. You can change direction, talk about something ordinary, or let the conversation rest.

The question is only the beginning

You can ask all three kinds of question and still miss the person if you are busy waiting for your own turn.

Stay with an answer long enough to hear it. Follow what interests both of you. Do not mistake a longer conversation for permission to ask anything.

There is no prize for getting past small talk quickly. Talking about a dog for half an hour can be a good conversation. Talking about someone's deepest fear when they did not want to can be a bad one.

The Board Walks offers time for conversations to find their own pace: a free five-mile walk every Saturday morning in 20+ cities, phones away, with an opening circle before we head onto the trail.

Bring a question if you have one. Follow the conversation if it goes somewhere else. Check your local walk details and RSVP before coming.

Find a Saturday walk in your city.

Stories, values, the future. Pick a direction, not a destination. Then pay attention to the person beside you.