How to Ask Genuine Questions

Co-authored by Christina Stathopoulos, PCC, ACCC and Hunter Rising

Last Updated: November 15, 2021 References

Do you want to build a closer bond when you’re talking with someone? If you really want to connect with someone, figuring out the right questions to ask can seem pretty difficult. Luckily, there are a lot of things you can do to make your chats more genuine so you learn more about each other. We’ll cover how to ask an engaging question and move on to some ways to show that you’re focused on the conversation!

1

Spark the conversation with personal news.

Sharing something first helps you form a genuine connection. If you want an easy way to break the ice, start your conversation with an interesting thing you’ve done or something that’s made you excited recently. By showing that you’re open and willing to share about yourself, the person you’re chatting with will feel more comfortable opening up to you as well.^{[1]
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- For example, you could say something like, “My partner and I adopted a new cat this weekend and it is so cute. Do you have any pets?”
- As another example, you might say something like, “My daughter rode her bike all by herself for the first time yesterday. What are your kids up to?”

2

Seek new information rather than repetitive topics.

You don’t add anything new to talk about if you ask about something you know. People usually don’t answer questions like “What’s up?” or “How are you?” fully since they’re so common and overused.^{[2]
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Expert Source

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach
Expert Interview. 15 October 2021.} Do your best to avoid asking disingenuous questions. Instead, dig a little deeper and ask about something specific so you can learn more about them.^{[3]
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- For example, you could ask, “What was the best part about your day today?” or “What are you looking forward to doing this week?”

3

Opt for open-ended questions.

Give the person a chance to talk so you get to know them better. Do your best to avoid yes/no questions since you’ll usually get a 1-word answer back. When you ask a question, try starting it with “what,” “how,” or “why” since that encourages someone to speak on the topic more. Start with some casual questions when you first start out, but don’t be afraid to test the waters with some more personal questions as you bond.^{[4]
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Harvard Business Review
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- For example, instead of asking “Did you have a good weekend?” you might try, “What were you up to this weekend?”
- As another example, you could ask “How’s your relationship with your family?” rather than asking, “Are you close with your family?”
- If you’re in a work setting, you could ask something like, “What led you to make these decisions on the project?” or, “How can I be the most helpful right now?”

4

Ask about topics the person likes.

Find out their interests to show you want to learn more about them. Everyone loves to talk about their passions, so try to find some common ground you have. Ask the person about their hobbies and what they enjoy doing in their free time. You could also just mention some current events or pop culture to see if they have anything to add to the topic.^{[5]
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- For example, if you know the person loves movies, you could ask, “What’s the best movie you saw in theaters this year?”
- As another example, if the person mentions they play soccer, you can ask something like, “What inspired you to get into soccer?”

5

Follow up to dig a little deeper.

Expand on something the person said to keep them talking.^{[6]
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Expert Source

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach
Expert Interview. 15 October 2021.} If you’re still curious about a topic after someone answers your questions, pick a point that they brought up and ask them to go on about it more. Try to get as many details as you can so you understand the person a little easier. Asking follow-ups also shows the other person that you’re interested in them, so they’ll be more willing to open up about themselves.^{[7]
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Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- For example, if the person mentioned moving to a new city, you could ask something like, “Where did you live before you moved here?” or “Why did you choose to move out here?”
- Remember that conversations are 2-way streets! Be sure to mention your thoughts and opinions on things too so the other person feels connected with you.

6

Stick to personal questions to build a connection.

Ask about the person’s life and interests to build a closer relationship. Every person has a different story, so be curious and learn more about them. Try any of these questions to delve deeper into the person’s life and find out more about who they are.^{[8]
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- What’s the most important thing I should know about you?
- What’s the driving force in your life right now?
- What’s the best thing that’s happened to you in the past week?
- When were you the happiest in your life?
- What’s something that you’re the most excited about right now?
- What’s been the most defining moment in your life?

7

Ask about company culture in a professional interview.

Learn about how an employer operates so you know if you’re a good fit. Rather than going into an interview without any questions, show that you’re truly interested and intrigued to work there. A few questions that you can try out include:^{[9]
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- How would you describe the culture of the organization?
- Can you tell me more about the team I’m working with and how it fits in the company?
- What do you like most about working for this employer?
- How has your role evolved since you began working for this company?
- If you could give one piece of advice to someone working here, what would you tell them?
- Where do you hope to see this department in the next 5 years?

8

Keep an open mindset.

Judging someone else prevents you from truly understanding them. Even if you disagree with something the person said, try to look at it from their perspective to get an idea of where they’re coming from. If you’re confused by what they’re saying, ask them to clarify what they meant or why they think a certain way so you understand their train of thought. The person will feel a lot more comfortable if you seem curious rather than judgemental right away.^{[10]
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Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- You don’t have to believe everything the person says, but at least give them a chance to explain before you make an assumption.

9

Maintain a casual, friendly tone.

Someone’s more likely to open up if you’re warm and inviting. Opening up and chatting with someone can be a little nerve-wracking, so take a few deep breaths to relax and act casual. Do your best to hide your nervousness by smiling while you talk. That way, you trick yourself into feeling more excited and the other person will feel a lot more comfortable sharing more personal information with you.^{[11]
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- Try smiling while you’re talking to sound happier and more personable.^{[12]
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10

Stay engaged with your body language.

Another person can tell if you’re disinterested just from your expression. As you’re chatting, turn your body toward the person. Be sure to make eye contact and nod along with what they’re saying so it looks like you’re more involved. Keep your arms at your side rather than crossed in front of you, since it could seem like you’re closed off from the point they’re making.^{[13]
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Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- Fidgeting a lot and looking away from the person may also make it seem like you’re anxious to get out of the conversation.

11

Avoid getting distracted.

Give the person your full attention so they know you care.^{[14]
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Expert Source

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach
Expert Interview. 15 October 2021.} While it may be tempting to look around or check your phone, stay focused on the person you’re talking to. Keep your phone in your pocket and on silent so you’re not tempted to check it. Actively listen to what they’re saying to ensure you’re hearing them correctly. Give them your full attention so you can build a genuine bond and feel connected with one another.^{[15]
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- Even glancing at your phone or watch could be a sign to the other person that you’re not interested, so keep it out of sight.
- Repeat things back to the other person to show that you’re listening and to get clarity on anything you’re confused by.
- If you're really listening and present in the conversation, then the next question you ask will undoubtedly be meaningful.^{[16]
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  Christina Stathopoulos, PCC, ACCC
  Certified Leadership & Life Coach
  Expert Interview. 15 October 2021.}

12

Steer away from rhetorical or leading questions.

Adding your own views to a question makes you seem less open. Asking rhetorical and leading questions makes it difficult for another person to voice their own thoughts. If you have an opinion of something, say it as a statement first. Then, ask a question to get the other person’s perspective on the subject so they have a chance to share their thoughts.^{[17]
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Trustworthy Source
Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source}
- For example, avoid something like, “You don’t think that will really work, do you?” since you’re forcing an opinion. Instead, try something like, “I have a few concerns about this project. What led to the decisions you made?”
- If you already know the answer to a question before you ask it, then you probably don’t need to say it out loud.

Community Q&A

Question

How do you ask someone better questions?

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach
Christina Stathopoulos is a Certified Leadership and Life Coach and the Founder of Hear Her Roar, a coaching service for women leaders. With more than five years of experience, she specializes in leadership development, relationships, empowerment, public speaking, and work-life balance. Christina holds a BA in Chemistry and English from Mount Holyoke College. She has also received her Professional Certified Coach Credential from The International Coaching Federation and Accomplishment Coaching Certification from Accomplishment Coaching.

Christina Stathopoulos, PCC, ACCC

Certified Leadership & Life Coach

Expert Answer

Personalize the question so only that particular person can answer it! Instead of asking "What's your favorite part about your job," you could ask a question that's really specific to the person's day-to-day life.
Question

What makes a bad conversation?

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach
Christina Stathopoulos is a Certified Leadership and Life Coach and the Founder of Hear Her Roar, a coaching service for women leaders. With more than five years of experience, she specializes in leadership development, relationships, empowerment, public speaking, and work-life balance. Christina holds a BA in Chemistry and English from Mount Holyoke College. She has also received her Professional Certified Coach Credential from The International Coaching Federation and Accomplishment Coaching Certification from Accomplishment Coaching.

Christina Stathopoulos, PCC, ACCC

Certified Leadership & Life Coach

Expert Answer

Not paying attention! A lot of times, people plan what they're going to say while the other person is talking instead of really listening to what they're saying.