Questions to Ask on a Coffee Chat
Engaging questions to ask during a coffee chat to build connections, learn about someone, and have meaningful conversations.
1What's something you're really excited about right now?
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What's something you're really excited about right now?
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Why this works
Opens up positive conversation and helps you connect with what's energizing them in their life.
2What's something you've been working on that you're proud of?
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What's something you've been working on that you're proud of?
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Why this works
Shows interest in their achievements and gives them a chance to share something meaningful they've accomplished.
3What's something you've learned recently that surprised you?
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What's something you've learned recently that surprised you?
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Why this works
Encourages intellectual conversation and helps you understand what's capturing their curiosity.
4What's something you're looking forward to in the next few months?
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What's something you're looking forward to in the next few months?
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Why this works
Shows interest in their future plans and helps you understand what's motivating them right now.
5What's something you wish you could tell your younger self?
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What's something you wish you could tell your younger self?
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Why this works
Brings wisdom and reflection to the conversation and helps you understand their perspective on growth.
6What's something you're grateful for that you don't often talk about?
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What's something you're grateful for that you don't often talk about?
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Why this works
Brings positivity to the conversation and helps you understand what's meaningful to them beyond the obvious.
7What's something you've been curious about or want to learn more about?
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What's something you've been curious about or want to learn more about?
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Why this works
Shows interest in their intellectual pursuits and helps you understand what's capturing their attention.
8What's something you've discovered about yourself recently?
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What's something you've discovered about yourself recently?
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Why this works
Shows interest in their personal growth and helps you understand how they're developing as a person.
9What's something you wish you could change about the world?
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What's something you wish you could change about the world?
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Why this works
Reveals their values and concerns and helps you understand what matters most to them.
10What's something you've been thinking about that you haven't shared with anyone?
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What's something you've been thinking about that you haven't shared with anyone?
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Why this works
Creates intimacy and helps you understand what's really on their mind.
11What's something you're proud of that you don't often get to talk about?
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What's something you're proud of that you don't often get to talk about?
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Why this works
Gives them a chance to share something meaningful that they might not usually discuss.
12What's something you've been working on improving about yourself?
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What's something you've been working on improving about yourself?
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Why this works
Shows support for their personal development and helps you understand their growth goals.
13What's something you've been excited about that you haven't had a chance to share?
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What's something you've been excited about that you haven't had a chance to share?
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Why this works
Gives them a chance to share good news and helps you celebrate their positive experiences.
14What's something you wish you could do more of?
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What's something you wish you could do more of?
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Why this works
Shows interest in their desires and helps you understand what they value and want to prioritize.
15What's something you've been thinking about regarding your future?
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What's something you've been thinking about regarding your future?
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Why this works
Shows interest in their long-term plans and helps you understand their hopes and dreams.
16What's something you've been struggling with that you'd like help with?
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What's something you've been struggling with that you'd like help with?
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Why this works
Shows you're there to support them and helps you understand how you can help them.
17What's something you'd like to know about me that you've never asked?
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What's something you'd like to know about me that you've never asked?
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Why this works
Encourages mutual sharing and helps you both learn more about each other.
18What's something you've been thinking about that you'd like to discuss with someone?
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What's something you've been thinking about that you'd like to discuss with someone?
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Why this works
Creates space for deeper conversation and helps you understand what's on their mind that they want to share.
19What's something you're grateful for that you don't often think about?
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What's something you're grateful for that you don't often think about?
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Why this works
Brings appreciation to the conversation and helps you understand what they value that might be overlooked.
20What's the most important thing you want me to know about you right now?
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What's the most important thing you want me to know about you right now?
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Why this works
Gives them a chance to share what's most important to them and helps you understand their current state.
Making the Most of Coffee Chats
Expert tips and techniques for getting the most out of these questions.
Best Practices
Be Present and Engaged
Give your full attention to the conversation and avoid distractions. Show that you're genuinely interested in what they're saying.
Ask Follow-up Questions
Show genuine interest by asking follow-up questions that help you understand their experiences and feelings better.
Share Your Own Experiences
When appropriate, share your own experiences to create mutual understanding and connection.
Question Sequences
The Positive Energy Sequence
The Deep Connection Sequence
Common Pitfalls
Don't Rush the Conversation
Give them time to think and respond fully. Don't rush them to answer quickly or move on to the next question too fast.
Avoid Being Critical
Don't criticize their answers or try to fix their problems unless they specifically ask for advice.
Don't Make It All About You
Focus on them and their experiences. Don't turn every question into an opportunity to talk about yourself.