Growing up, many of us were taught that being nosy was wrong, like you were crossing a line. But as an adult, asking questions that go beneath the surface is how you build deeper relationships. The right questions can help you learn more and stand out as a thoughtful and helpful person. 

In my book, "Wild Courage: Go After What You Want and Get It," I write about how to embrace insatiable curiosity, not for gossip, but for genuine understanding and connection. It's a superpower. 

Curiosity is a skill that can be cultivated. Children under five ask up to 180 questions a day. But adults often suppress that instinct, and in doing so, we miss out on opportunities to learn and grow together. 

Don't be afraid to ask these 7 powerful questions

Asking thoughtful, nosy questions shows you're invested in your job and makes you look like someone who's got great ideas. It says you aren't afraid to ask the important stuff to someone in a position of power.

Here's how to turn ordinary conversations into extraordinary opportunities for growth and connection:

1. "What's one thing you wish you knew when you were in my shoes?"

This is a great question to ask your boss. It shows an eagerness to learn and benefit from their experience.

It also signals humility — you're not looking for shortcuts, you're asking to learn from their experience. If you sense they are comfortable being vulnerable, you could ask, "What's been one of the hardest leadership lessons for you to learn?"

2. "What changes do you foresee in our industry, and how can I prepare?"

This is an ideal conversation starter for your manager's boss, or someone who is influential in your field. It demonstrates you're thinking ahead and are ready to adapt.

Another way to tee up that kind of conversation is to ask, "What shifts in the market are you watching the most closely right now?"

3. "How did you recover from a past failure?"

This is a great question for a mentor or someone you look up to. It shows you seek wisdom beyond their success stories. It also normalizes failure, invites honesty, and quickly builds connection.

If you're looking for something lighter, you could ask, "What's something you used to believe about success that you've since outgrown?" or, "How do you approach decisions when you have no clear answer?"

4. "What qualities do the top performers in this role have?"

Have this ready to go in a job interview. It demonstrates that you're already envisioning success in the role.

If you want to better understand the team dynamics, you could ask, "How would you describe the team's communication style?"

5. "What's the most exciting thing that happened to you this week?"

I love this as an icebreaker because it instantly helps you move beyond surface-level small talk and you can get a real sense of what matters to your conversation partner.

If you're feeling bold, you could ask, "What's a goal you're working on that nobody really sees?"

6. "What's something people usually get wrong about you?"

This is great when you're spending time with a new friend or colleague. It's deceptively simple but unlocks depth, vulnerability and connection.

If you want to give them a chance to offer a more well-rounded view of their personality, you might ask, "How would your closest friends describe you in five words?"

7. "What's the best compliment you've ever gotten?"

I love this as an icebreaker for any social setting: a networking event, a party, brunch. It sends good vibes and makes people smile.

It also gives people permission to feel good about themselves, which builds instant emotional resonance. You are essentially asking, without overwhelming them, "What about you has been truly seen or appreciated?" 

Embrace curiosity for career growth and success

Asking smart, unexpected questions shows you're curious and ready to stand out. People notice that, and they love talking about themselves. 

Research shows people's pleasure centers light up when they share their opinion or talk about themselves. When you make people feel good, they're bound to like you more, and likability matters in your career. 

So, the next time you're in a meeting, a one-on-one or sweating it out in an interview, resist the urge to play it safe — and whip out these questions instead. They might just help you unlock your next big opportunity.

Jenny Wood is a New York Times bestselling author, speaker, former Google executive, and former Harvard Business School researcher. Her goal is to empower ambitious people to break the mold, be better leaders, build influence, and reach their full potential. In her new book "Wild Courage: Go After What You Want and Get It," Jenny breaks down nine bold traits that defy conventional career advice. Jenny is the founder of Own Your Career, one of Google's largest career programs. She has been featured in NBC, Bloomberg, Harvard Business Review, Forbes, and Business Insider. She lives in Boulder, Colorado with her husband and two children and is in constant pursuit of the perfect zucchini bread recipe.

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