In a world that feels increasingly disconnected, the right questions—and a willingness to listen—can bring people, solutions, and better results closer than ever.
What if the solution to your biggest challenges—at work or at home—wasn’t an answer at all, but a question?
Not a dodge. Not a delay. But one of the most underused—and highest-return—strategies we have: genuine, curiosity-led conversations.
Right now, leaders are navigating challenges that seem more complex by the day:
- Team misalignment and siloed communication
- Burnout and disengagement
- Resistance to change and technology
- Lack of buy-in or clarity
- Missed deadlines and surface-level collaboration
And while there’s no silver bullet, I’ve always been told this: if you want better answers, you need to ask better questions.
Questions that make people feel seen. Questions that turn insight into action. Ones that shift conversations from transactional to transformational.
Because while this post is about connection at its core, it’s not just about fighting loneliness.
It’s about unlocking one of the strongest assets every company, community, and family has—each other.
Why You Should Question Real Connections
One of the best pieces of advice I ever received came from a mentor, Patricia Fripp. She said, “The key to connection is conversation. The key to conversation is questions.” I’ve seen that play out time and time again.
Whether I’m leading a workshop, sitting down with an executive team before delivering a keynote, or having dinner with my family—asking the right question changes everything.
But what makes a question “right”?
At the heart of every strong relationship—at work, at home, in life—is the feeling of being truly seen and heard. Great questions do that. They challenge assumptions and disrupt stale patterns.
They show we care enough to slow down, truly listen, and stay open to a perspective or answer we didn’t already have packaged and ready to go.
That kind of curiosity isn’t soft. It’s strategic. It leads to better decisions, stronger teams, and more meaningful progress. In a world where everyone’s rushing to offer answers, the people who pause to ask a thoughtful question stand out—and build trust faster.
In my experience, questions fall into two categories: Discovery Questions and Solution Questions. Each plays a critical role in deepening connection and moving things forward.
Let’s start with Discovery.
Discovery Questions: Build the Bridge Before You Cross It
Before you can solve a problem, you have to understand it. And before you can lead someone, you have to see them.
That’s where Discovery Questions come in.
These are the kinds of questions that uncover someone’s perspective, hopes, frustrations, or unspoken expectations. They’re not about fixing. They’re about finding. About exploring the deeper context behind what’s working, what’s not, and what someone really wants to see happen next.
I use these in nearly every setting—coaching calls, one-on-ones, team offsites, even casual conversations. Because they are the key that unlocks connection, credibility, and trust.
When people feel heard, they open up. When they open up, they invest. And when they invest, your collaboration gets stronger, faster, and more aligned.
Here are a few Discovery Questions I keep in my back pocket:
- What would a home run look like on this project?
- What’s your biggest worry right now?
- What are you loving about this process?
- What’s your biggest hope for this new initiative?
- What’s something you wish more people asked you about?
Use these to explore: values, motivations, fears, expectations, goals, and context. Think of them as relationship-deepening questions—open-ended, reflective, and often beginning with what or how.
While they can lead to rich insights, “why” questions often feel confrontational—especially in high-stakes or emotionally charged settings. They ask people to justify themselves, which can trigger defensiveness—especially if they don’t know or understand the actual cause.
They also tend to require deeper reasoning and emotional excavation, which takes time and psychological safety—not always realistic in fast-paced conversations.
You’ll often get better results by leading with what or how, which invite clarity without putting someone on the defensive. For example:
- Instead of “Why did you do it that way?” → try “What led you to approach it that way?”
- Instead of “Why isn’t this working?” → try “What’s getting in the way right now?”
These questions don’t just gather facts—they help people feel safe enough to share what’s beneath the facts. That’s where real trust starts to form.
A word of caution here: don’t ask what you’re not willing to truly listen to. Discovery is only powerful when it’s paired with attention. The goal isn’t to be interesting—it’s to be interested.
Once you’ve listened—really listened—the next step is helping people move forward. That’s where Solution Questions come in.
Solution Questions: Turn Insight Into Action
Where Discovery Questions help you uncover the landscape, Solution Questions help you chart the path. They take what you’ve heard and begin to translate it into progress: a decision, a direction, a next step.
The shift here is subtle but significant. You’re no longer just understanding—you’re helping to activate, challenge, and grow. And when done with humility and clarity, this is where the magic happens.
Here are a few Solution Questions I often partner with my Discovery questions above.
- Who needs to be included on this project to hit that home run?
- What’s the first thing we could do to alleviate that concern?
- How could we leverage what’s working to overcome what’s not?
- How can we start to get buy-in for that next initiative?
- What does a meaningful “next step” look like for you?
Use these to generate momentum: to help people consider actions, clarify roles, make decisions, or co-create next steps. These questions assume forward movement—but leave room for the other person to shape how that happens.
These questions are still rooted in curiosity—but they carry momentum. They take the conversation from awareness to alignment and from understanding to ownership.
One quick note of caution: A trap I’ve seen leaders fall into is lingering too long in the discovery phase. It’s safer. It’s non-confrontational. And it can also wear everyone out and erode morale and trust in the process.
If your goal is real trust and real results—not just comfort—then it means helping people move through uncertainty, not just sit with it. As I say in my book, “It can be a delicate navigation, but knowing when it’s time to move from the mud to the highway is the leader’s job.”
Use the above questions, and others like them, to help you put a strong hand on the wheel.
Real Connection Starts with Real Questions
At a time when people are moving fast, making assumptions, and struggling to feel seen—connection isn’t a luxury. It’s a leadership imperative.
And the fastest way to deepen that connection isn’t a team offsite or a perfect personality profile. It’s a well-placed question, asked with genuine curiosity and a willingness to truly listen.
Because the truth is: people don’t just want to be fixed. They want to be heard. They want to feel like their thoughts matter, their concerns are valid, and their ideas are part of the solution. The right questions unlock all of that—and turn your conversations into catalysts.
So before your next team meeting, coaching session, or coffee with a colleague, don’t prep a speech.
Prep a question.
And then listen like it’s your job. Because it is.
As the leading voice on trust, David Horsager helps leaders and organizations transform the way they connect, communicate, and perform. His keynotes, workshops, and Trust Edge Certification programs are designed to build real trust—and real results. Want to bring this message to your event or team? Let’s talk.