When meeting someone new, whether in a professional or personal context, it can be challenging to move the conversation beyond small talk to really connect with the other person. Having a repertoire of thoughtful questions to ask can help break the ice and lead to more meaningful interactions. In this article, we will explore impactful questions to ask when looking to build rapport, understand someone’s story, and uncover common ground.
Questions to Understand Their Story
Getting to know someone often starts by understanding their personal narrative. Asking about their past and present can reveal insightful anecdotes and details about their life journey. Here are some questions that can unveil their story:
Where are you from originally?
This opens the door to learn about where they grew up, their family background, hometown stories, and what led them to live where they are now. Based on their answer, you can ask follow-up questions about what they miss and love about their place of origin.
What were you like as a child?
This provides a glimpse into their personality and interests growing up. You can ask what activities they enjoyed, what their childhood dreams were, and how they’ve carried parts of their childhood into adulthood.
How did you get into your current field?
Their career path reveals motivations, pivot points, and passions. Ask about their big “a-ha” moments, challenges along the way, mentors who made an impact, and how they envision their career evolving.
What do you geek out about?
We all have something we get excited to talk about, whether that’s astrophysics, 19th century literature, bird watching, or systemic inequality. This question uncovers their nerdy side and what compelled them to dive deeply into a topic.
What’s your superpower?
This lighthearted question allows them to share something they’re talented at or proud of. It could be an actual skill like speed reading, a personality trait like empathy, or something more tongue-in-cheek.
What were some of the biggest lessons you learned this past year?
Look at the last 12 months of their life. What changed? What realizations did they have? Asking this provides a snapshot of their emotional and intellectual journey over the past year.
Questions to Understand Values and Beliefs
Our values stem from our core beliefs and shape our worldview. Understanding someone’s perspective provides insight into their priorities and motivations. Here are some questions to uncover values:
What matters most to you in life?
This reveals their guiding principles and what they prioritize above all else, whether it’s family, faith, knowledge, justice, creativity, humor, adventure, etc. Follow up by asking why these things matter so much to them.
How do you define success?
People have vastly different measures of success. Is it fortune and fame, personal growth, contributions to society, overcoming challenges, strong relationships? Their definition illuminates their dreams and what brings meaning to their life.
What global issue concerns you the most and why?
The causes they care about reflect their sense of morality and desire to make an impact. This could range from human rights issues to environmental conservation to poverty alleviation. Their why gives context into their values.
When have your values been challenged? How did you respond?
Learning how people uphold their values when tested reveals their character and integrity. Ask about a time they had to defend their beliefs or make a hard decision based on their principles.
Who inspires you and why?
Understanding their role models provides insight into who they look up to and the qualities they aspire to embody themselves. Ask what they find inspiring about this person.
If you could change one thing about the world, what would it be?
This thought-provoking question uncovers their vision for a better future and what they believe is most broken or in need of fixing in society.
Questions to Understand Dreams and Aspirations
Hopes and dreams are a core part of what drives people. Asking about their ambitions can illuminate their deepest desires. Here are some questions that uncover dreams:
If you had a magic wand, what’s the one thing you would change about your life?
This reveals their ideal scenario and surfaces what they feel may be missing or needing improvement in their life currently. Give them permission to think big without limits here.
What would your perfect day look like? Walk me through it.
Having them describe their fantasy day from start to finish unearths what their daily routine would include if time and obligations didn’t get in the way. This allows you to understand their perfect life vision.
Where do you see yourself in 5 years? 10 years?
Their goals and milestones for the future demonstrate their path of growth. Ask about their biggest personal and professional objectives and how they envision getting there.
What are you most excited about right now?
Knowing their current passions and things bringing them joy gives insight into who they are in the present moment. See what important projects, upcoming events, new hobbies, or relationships are lighting them up.
What adventure is on your bucket list? Why does it inspire you?
Bucket list goals reflect deep desires to explore, grow, and experience wonder. Asking about the one adventure that excites them most reveals the thrill they want to chase.
If you could master any skill, what would it be?
This surfaces talents they aspire to develop, from artistic skills like photography to physical feats like running a marathon. Their response demonstrates domains they want to grow and expand in.
Questions to Find Common Ground
Discovering mutual interests, experiences, and opinions is key to making connections. Here are questions to uncover commonalities:
What’s your favorite place you’ve ever traveled to and why?
If you’ve been to the same place, you can swap stories and memories. If not, you can discuss what draws you both to that destination.
What books, movies, shows, music are you into right now?
Sharing current pop culture obsessions is an easy way to bond over similar tastes and recommendations.
Do you have any funny or embarrassing work stories you’re willing to share?
Workplace mishaps tend to draw laughter and empathy. Swapping “can you believe that happened” stories fosters camaraderie.
Do you have any nicknames – either given to you or ones you wish you had?
Talking about nicknames (like childhood ones given by family or ones we secretly want) taps into a shared sense of fun and humor.
What popular trends did you participate in when you were younger?
Bond over crazy fads, clothing, sayings, toys, and moments in pop culture you experienced growing up.
What’s your go-to late night snack?
Food is a universal connector. Find common cravings and kitchen raid favorites.
Questions to Go Deeper
Once you’ve established some rapport and trust, you can dive deeper with more thought-provoking questions:
What are some of your fears or insecurities?
Being vulnerable builds intimacy quickly. Share your own fears first before asking someone else.
What keeps you up at night worrying?
Knowing their deepest worries reveals their mental and emotional landscape and what occupies their mind.
When was the last time you felt completely alive? What were you doing?
Look for peak experiences where someone felt joy, wonder, purpose. Understand their definitions of fulfillment.
What problems in the world feel unsolvable to you?
This surfaces the issues that concern them the most and problems they may have lost hope in being addressed.
What are some of your contradictions or hypocrisies?
We all have inconsistencies between our intentions and actions. Admitting hypocrisies fosters authenticity.
What parts of yourself are you trying to develop or heal?
Asking about self-improvement goals underscores our shared desire for growth. Look for common ground in vulnerability.
What have you had to unlearn and relearn on your life journey so far?
Discussing insights that changed our viewpoints demonstrates our ability to continuously evolve our perspectives.
What questions do you spend a lot of time thinking about?
The questions that preoccupy our minds reveal the mysteries, riddles, and enigmas that intrigue us. Discussing these big questions creates bonding.
If you knew you couldn’t fail, what dream would you set out to accomplish?
Removing limitations allows someone to get to their core desires. See what grand vision emerges when fear of failure is taken out of the equation.
Questions that Create Dialogue
The best connections are formed through back-and-forth sharing and storytelling. Rather than asking questions with simple one-word answers, pose open-ended ones that create dialogue:
What purchase have you made that you consider a great investment?
This encourages storytelling rather than just listing an item. Share why that investment was worthwhile and how it paid off.
What’s the most surprising self-realization you’ve had recently?
Rather than a short “I realized X,” have them expand on what triggered the insight, how it impacted their worldview, and what shift it created.
What’s something you believe that other people think is crazy?
Rather than a simple statement of belief, have them build out their reasoning and thought process behind it.
What random acts of kindness have meant a lot to you recently?
This taps into emotional experiences versus just listing nice things people have done. Share the backstory and significance.
What little moments made your day better today?
Instead of just quick mentions, have them recount details that share the delight or meaning behind them.
What are some phrases or mantras you find encouraging? Why do those resonate with you?
Rather than just stating a mantra, share how you came across it, what circumstances make it feel meaningful, and how it motivates you.
Wrap Up Questions
As you wrap up your conversation, here are some final thoughtful questions:
How do you think we can build more meaningful connections between people in our society today?
This surfaces their perspective on how we can bring more empathy and understanding to our relationships and communities.
What possibilities do you see in the world today that give you hope?
Ending on optimism and inspiration fuels a vision for change and progress.
What have you learned from me during our conversation? What strings resonated with you?
This mutual reflection fosters growth, perspective-taking, and appreciation of diverse viewpoints.
What are your hopes for the future of our relationship moving forward?
Articulating a shared vision for possibilities moving forward establishes intention for meaningful connection over time.
Key Takeaways
Here are some top tips to keep in mind when looking to connect more deeply with someone new:
- Ask open-ended questions that create dialogue versus yes/no questions
- Build on their responses and share your own stories to find common ground
- Aim for questions that reveal their values, dreams, and motivations
- Don’t shy away from thought-provoking or personal questions as trust builds
- Discuss questions you’re both curious about to bond over shared wonderings
Meaningful interactions rest on mutual understanding, vulnerability, and a shared quest for growth. Approach connecting with people as an adventure where you both can explore new perspectives and possibilities.
Conclusion
Forging genuine connections requires slowing down, stepping beyond small talk, and asking the right open-ended questions. Moving beyond the surface to understand someone’s story, beliefs, aspirations, and challenges allows trust and rapport to blossom. Keep these suggested questions in mind as guideposts to navigate conversations in uplifting directions. With care and courage, our exchanges with others can become rich opportunities to learn, grow in empathy, and appreciate both the uniqueness and universality of our human experience. When in doubt, speak from the heart and listen deeply. These are the ingredients for cultivating bonds that withstand the test of time.