One skill that can transform your career, relationships, and even your life, is the ability to ask better questions. Questions are the ultimate tool for learning, connecting, and innovating.
The Art of the Question
However, most people don’t ask enough of them—or worse, they ask the wrong ones. I’ve spent decades working with some of the most remarkable people on the planet, and if there’s one thing they all have in common, it’s this: they know how to ask the right questions at the right time.
Let’s break down how you can master this art.
Start with Curiosity
The best questions come from genuine curiosity. Stop trying to sound smart or impress people, and instead, focus on what you truly want to know.
When I interviewed Jane Goodall, her curiosity about chimpanzees led her to challenge everything we thought we knew about them. She didn’t just ask, “What do chimps eat?” She asked, “What can their behavior teach us about ourselves?” That’s the kind of curiosity that leads to breakthroughs.
Do Your Homework
The quality of your questions is, ironically, directly related to how much you already know. That is, the more homework and preparation you do, the better your questions will be.
If you think reading the Wikipedia entry or ChatGPT summary of a person, product, or company is sufficient and you can “rise to the occasion” because you are “quick on your feet,” you are deluded.
And, I hate to tell you, people can tell when you’re not prepared, and you’re winging it.
Make It Safe to Answer
People won’t open up if they feel judged or intimidated. Create an environment where it’s safe for them to share their thoughts, even if those thoughts are critical or uncomfortable.
Jeff Wetzler, who developed the ASK framework and wrote the book Ask, emphasizes the importance of lowering barriers to honest communication. A simple phrase like, “I’d love your honest feedback on this,” can make all the difference.
When people feel safe, they’ll tell you what you need to hear—not just what you want to hear.
Ask Open-Ended Questions
Avoid questions that can be answered with a simple “yes” or “no.” Open-ended questions invite deeper thinking and richer responses.
Alison Wood Brooks refers to this as uncovering the “hidden architecture” of conversations—questions like, “What’s the most surprising thing you’ve learned recently?” or “How do you see this evolving?”
These kinds of questions lead to insights you’d never get otherwise.
Listen More Than You Talk
Asking great questions is only half the battle—you also need to listen. And I mean really listen, not just wait for your turn to talk.
Alison’s research also shows that active listening is a superpower in conversations. It’s not just about hearing words, it’s about understanding emotions, intentions, and unspoken cues.
When you listen deeply, you’ll find follow-up questions come naturally.
Practice, Reflect, Improve
Like any skill, asking better questions takes practice. Start by auditing the questions you ask.
Are they thoughtful? Do they encourage meaningful dialogue? If not, tweak them.
Jeff Wetzler calls this “conscious incompetence”—recognizing where you’re falling short and working to improve. Over time, you’ll develop a repertoire of high-quality questions that come naturally.
Use Questions to Build Relationships
Great questions don’t just uncover information—they build trust and connection.
When you ask someone about their experiences, challenges, or dreams, you’re saying, “I see you, and I care about what you have to say.” That’s powerful.
Whether you’re leading a team, pitching an idea, or just having coffee with a friend, the right questions can deepen your relationships and open doors you didn’t even know existed.
