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29 great questions to get to know people and boost your confidence

May 25, 2022 - 12 min read


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Why you should ask questions

Everyday questions for anyone

Personal questions

Fun questions

Workplace questions

How to get good at asking questions

Building self-confidence

Let’s start a conversation

We’ve all been there: You just started a new job, it’s Friday afternoon, and the office calls it quits early for happy hour. It’s your first time talking to your co-workers in a social setting. 

Whether you're an introvert or an extrovert, this situation is nerve-wracking. It’s hard to put yourself out there and build new relationships and make friends. Instead of overthinking, focus on your colleagues. If you head to social events with interesting questions and conversation topics in mind, you’ll find it easier to get to know people. 

Asking questions is a vital communication skill that will get you further in life. Let’s go over some of the best questions to ask to get to know someone.



Why you should ask questions

Talking about yourself and sharing details about your life is cathartic — and it’s also a key building block for deeper relationships.

Here are some other benefits of asking questions:

  1. You might learn something surprising. Everyone has different experiences and backgrounds. Maybe a colleague studied something interesting in college. Or they visited a country on your travel bucket list. You never know what fun facts will come out in conversation.
  2. You’ll get out of your head. We’ve all sat through rounds of icebreaker questions to put everyone at ease on our first day at work or summer camp. It’s easy to retreat into your mind when nervous about social interaction.
    You might be worried about how you look or are afraid of saying something silly. Asking questions puts your attention on the other person instead of yourself. You may find that your interest and curiosity help you to make a good first impression, too.
  3. You may feel less alone. Being a new employee is lonely, but asking questions will help you find common ground with others. Who knows? You might find your next bandmate or gym buddy.

Meeting new people can be intimidating, and it’s okay to ask for help. At BetterUp, our coaches will always be in your corner. We can help you find your voice and strengthen your communication skills, so you’re ready for whatever life throws at you.

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Everyday questions for anyone

Here are some good questions to ask to get to know someone, kick-start bonding, and open the door for deeper topics later on. These are great everyday questions for colleagues and acquaintances, as well as your family members or loved ones. 

  1. What TV show have you binged recently?
  2. What is your favorite book?
  3. What’s your favorite type of restaurant?
  4. What’s your go-to drink?
  5. Do you have any hobbies?
  6. Do you spend a lot of time on social media?
  7. Who is your favorite fictional character?

As they answer, you can look for things you have in common. Offer your own thoughts. Ask follow-up questions. A good conversation will be flowing before you know it.


Personal questions

If things are going well, here are some questions to ask to get to know someone deeply. Asking more personal questions can help you build trust and lead to deep conversation:

  1. If you had to pick a movie to describe your life, what would it be?
  2. Have you ever tried meditation?
  3. What should everyone experience in their lifetime?
  4. If you had all the free time and resources in the world, what would you do?
  5. Why did you choose the career that you did?
  6. What’s your biggest fear?
  7. What is your earliest childhood memory?
  8. What’s a deal-breaker on a first date?
  9. What are some of your pet peeves?

As long as you’re both comfortable, these questions will help build deeper connections. You may even find your next best friend. There’s no best question to ask to get to know someone, but some questions let you learn about someone more deeply. 

Just make sure you’re asking tactfully and not prying at someone’s personal life. Asking invasive questions is the last thing that your attempts at small talk need. Stay tuned to people’s body language. If they look away or frown, those are signs to avoid personal questions.


Fun questions

It’s also okay to be a bit silly. Don’t be afraid to use your imagination and chat about your guilty pleasures. Here are some fun examples that could yield surprising answers:

  1. What’s the craziest thing you’ve seen someone do while driving?
  2. If you had to choose a new name, what would it be? Why?
  3. What’s the worst thing you’ve ever smelled?
  4. What is a well-known fact that becomes unnerving the more you think about it?
  5. What would you do if you found out you were living in a sitcom?
  6. If you could eat one food for the rest of your life, what would it be?

Who knows what rabbit hole you might find yourself in? And if things get too weird, you can always redirect to a different topic.


Workplace questions

Not all questions are workplace appropriate, so it’s important to be mindful of context. It might help to focus on work to avoid potential awkwardness. Here are some examples:

  1. Did you consider your childhood dream job when choosing a career?
  2. What piece of advice would you give your 18-year-old self?
  3. What is your favorite way to prepare for a meeting?
  4. Where is the best place to get a coffee around the office?
  5. What made you want to work at this organization?
  6. What’s on your career bucket list?
  7. What was your first job?

How to get good at asking questions

Once you know what questions to ask to get to know someone, you need to keep things flowing. Here are some guidelines to keep in mind as you chat away.

Be curious

Ask genuine questions. What do you want to know about this person? People will be more responsive if they feel you are interested in building authentic connections.

Avoid rapid-fire questions

Remember, this isn’t an interrogation. The goal is to relax and start people talking — not to hammer someone with questions. Questions are the starting point, and hopefully, the rest will come naturally. If there’s ever a lull, you can slip in another question when it feels right.


Be sure to use active listening when hearing their answers. Show interest through receptive body language and ask follow-up questions based on what they say.

Read body language

Body language can speak louder than words. Pay attention to facial expressions, hand gestures, mannerisms, eye contact, physical behavior, and tone of voice. Body language gives you cues as to whether your conversation is going well.


Building self-confidence

It’s natural to feel uneasy when meeting new people. You may feel uncertain about how they will respond to your conversation or fear they won’t accept you. In the early days of human evolution, acceptance meant life or death. It meant we had less access to food and were more vulnerable to predators. But, in the modern world, these feelings interfere with meaningful connections.

Self-confidence can help ease your nerves. In the long run, it can also make you happier and more adaptable to the uncertainties of life.

Here are some tips to help keep your confidence up:

  1. Stop comparing yourself to others. You are already a fantastic person. Why waste time wanting to be someone else?
  2. Have positive self-talk sessions. This tactic can help quell any doubts that you aren’t as great as you really are.
  3. Be proud of what you have accomplished so far. Look back on your proudest moments. You worked hard to get where you are. Own it! You may even want to give yourself a reward when you achieve something meaningful.

Let’s start a conversation

Now that you have starter questions to ask to get to know someone, how about some practice? BetterUp offers personalized coaching to help you be the best version of yourself. Work with our coaches to develop strong communication skills and form deeper relationships.

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Published May 25, 2022

Elizabeth Perry

Content Marketing Manager, ACC

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