If you’ve ever tried to ask someone directly, “So… what matters most to you?”, you know how awkward it can land. Too big. Too vague. Too much like a job interview disguised as intimacy.
The truth is, people show their values all the time—through choices, stories, frustrations, and even offhand jokes. You just have to know where to listen. And sometimes, asking the right indirect question opens the door to those values more naturally than going straight for the jugular.
These five questions aren’t tricks or personality tests. They’re conversational keys—designed to reveal what someone prioritizes, protects, or pursues in life, without ever needing to ask them point blank. Think of them as gentle mirrors that reflect what matters most.
1. “When was the last time you felt really proud of yourself?”
Pride is one of the clearest windows into someone’s values. What we choose to feel proud of says a lot about what we care about most deeply. Some people light up about career wins. Others recall moments of kindness, creativity, or resilience.
When you ask this question, notice both what they highlight and why it mattered to them. A story about finishing a marathon may not be about athleticism at all—it could be about discipline, perseverance, or proving something to themselves. Pride isn’t just about achievement; it’s about alignment with what feels meaningful.
Ask It Out Loud: “What’s a small win lately that made you feel good, even if no one else noticed?”
2. “What kind of moments make you lose track of time?”
Time is the most democratic resource we all share—and how someone naturally spends it is one of the clearest indicators of what they value. When people lose themselves in something, it’s usually because it hits that sweet spot of joy, engagement, and alignment.
Listen closely here: if they mention spending hours cooking for friends, connection and hospitality might matter to them. If it’s tinkering with spreadsheets, it could be structure, problem-solving, or mastery. The actual activity is less important than the underlying value it reflects.
This question works because it sidesteps the pressure of “What do you value?” and instead asks, “What feels alive for you?”
3. “Who do you admire—and what is it about them that resonates with you?”
We often project our aspirations and values onto the people we admire. If someone says they admire their grandmother for her independence, it may show a high value for self-sufficiency. If they talk about a public figure’s ability to inspire, they might care deeply about influence, service, or leadership.
What’s powerful here is that admiration can be aspirational. Sometimes people admire qualities they wish they had more of themselves. That gap between what they admire and where they feel they are can be fertile ground for connection, encouragement, and even collaboration.
Ask It Out Loud: “Who in your life taught you something that still shapes you today?”
4. “What’s a decision you made that you’d never trade—even if it complicated your life?”
Values don’t just show up in what we like—they often show up most clearly in what we’re willing to sacrifice for. This question pulls out moments where someone chose alignment over convenience.
Maybe they walked away from a high-paying job to start a business. Maybe they moved cities to be closer to family. Maybe they ended a relationship that didn’t honor their needs. Each of those choices reflects a core value—autonomy, loyalty, authenticity—that outweighed other options.
Asking about decisions in this way allows people to share a story without feeling put on the spot. It frames complexity as evidence of integrity, which makes the conversation feel more supportive than judgmental.
5. “When life feels overwhelming, what helps you come back to yourself?”
Stress is a sneaky compass. What people turn to in their hardest moments often reveals what they hold sacred. For some, it’s solitude or nature—suggesting they value restoration and grounding. For others, it’s reaching out to friends or family—signaling community and connection.
This question isn’t just about coping; it’s about alignment. It asks: Where do you return when things feel off-balance? What stabilizes you? Their answers can reveal everything from creativity to spirituality to resilience. And sometimes, it simply uncovers the rituals and anchors that make life sustainable.
Ask It Out Loud: “What’s something simple that always helps you reset, no matter how messy the week gets?”
Why These Questions Work (and “What Matters to You?” Often Doesn’t)
When you ask someone directly about their values, they’re forced into abstraction. Words like family, honesty, kindness are common—but they don’t tell you how those values actually live in their world.
These five questions work because they ground values in stories, actions, and choices. They don’t demand that someone name their philosophy of life. Instead, they invite them to reflect on real experiences—moments of pride, admiration, sacrifice, joy, and reset. That’s where values show up in their clearest, most human form.
And perhaps more importantly, these questions don’t feel like interrogation. They feel like invitations.
The Art of Listening Between the Lines
As useful as these questions are, their real power isn’t in asking—it’s in listening. People may not name their values outright, but they’ll hint at them in the why behind their answers.
If someone says they’re proud of mentoring a junior colleague, the value might be growth, generosity, or legacy. If they lose track of time while organizing spreadsheets, it could be about order, clarity, or efficiency.
Your role is not to analyze like a psychologist, but to notice like a friend. To reflect back what you hear: “Sounds like helping others grow really matters to you.” This gentle mirroring can make people feel both seen and understood.
How to Use These Questions in Everyday Life
The beauty of these questions is their flexibility. You can use them:
- On a walk with a friend
- Over dinner with a partner
- In a team-building session at work
- Even in a quiet moment of journaling with yourself
The key is not to rush. These aren’t rapid-fire prompts—they’re slow-burn invitations. Let the silence stretch. Let people think. Let the answers surprise you.
Sometimes the best conversations aren’t the ones you push forward—they’re the ones you let unfold.
Connection Isn’t About Scripts, It’s About Signals
At the end of the day, these five questions aren’t magic spells. They’re simply tools that make it easier to notice what’s already there: the signals of someone’s values shining through in the stories they tell, the people they admire, the moments they hold onto.
You don’t need to ask, “What matters to you?” to find out what matters. You just need to be curious enough to ask differently—and kind enough to listen fully.
