From Jenny Wood, author of Wild Courage: Go After What You Want and Get It…
___________________________________________

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?”