10 questions I wish I’d asked more to turbocharge my career

Julie Zhuo
Mar 29 · 8 min read

“The art and science of asking questions is the source of all knowledge,” Thomas Berger said.

If I could go back in time and tell my new college grad self what the secret to a rocket ship career is, it would simply be this: Ask More Questions. Ask them of your managers, the peers who work closest to you, and anyone whom you admire and feel they have something to teach you. The best mentorship relationships start from a good, earnest question. Which ones specifically? My new book, The Making of a Manager, goes into great details about the questions that new leaders should ask themselves and their reports. Here is a summary of the top 10.

1. Where have I had the most impact over the past few months, from your perspective?

The easiest way to develop self-awareness is to regularly ask others for honest feedback, which is harder than it sounds because it requires vulnerability. What if the feedback is critical or not what you expect? That’s why I like this question. It’s the most positive framing of feedback, and therefore the easiest way to ease yourself into the habit of asking. Are there things you’re proud of that others are noticing as well? Or do your peers have a different view of what you’ve done that’s most impactful? This is a great question for your manager, as well as practically any peer.

2. What do you think it would look like for me to be twice as good at what I do, or for this project to go twice as well?

We tend to rise only as far as what we can envision. If your bar for “amazing work” is say, at level nine, and you hit it, you probably won’t be gunning to do more. But if someone says to you, “Try going for level 15 — here’s what that looks like,” suddenly, you have a new goal in front of you. As they say, shoot for the stars, and you’ll land on the moon. Bonus points: this question shows others that you’re eager, proactive, and always aiming for more.

3. I’m trying to get a better handle on my blind spots. What kinds of things, from your perspective, do I have a habit of missing or dismissing too quickly?

This is one of the best questions to cultivate your self-awareness, to open yourself up in a way that invites honesty and trust, and to show that you care more about growing and learning than you do about protecting your ego. It’s your way of saying, “Help me become better.” And it’s packaged in a way that acknowledges that having blind spots is universal, not a personal weakness. You’re just self-aware enough to want to uncover what yours are.

4. What’s hard for you in your job?

This is a perfect question to ask your manager or someone who has a job that you might one day like to have. You’ll get a sneak peek at what trials you may face ahead and how you might best prepare. It’s also the perfect question to ask to build a closer bond with someone you work with. You’ll be rewarded with a hearty dose of empathy and a better understanding of someone else’s challenges. Because face it, every job has its towering mountains and unglamorous uphill climbs, and by being curious about other people’s journeys, you’re guaranteed to take away an interesting story or a new perspective.

5. How do you prioritize your time?

More than that, asking others how they prioritize their team gives you a glimpse into what they consider valuable. Especially with managers, mentors, or people whose careers you’d like to emulate, this question also sheds light on what these folks consider most important in their jobs.

6. What’s something interesting you’ve learned in your job that most people don’t know?

7. You’re really exceptional at X. How do you do it so well?

8. What’s your biggest problem, and how can I help?

9. I’d love to [learn about/do more of/achieve] X. If you come across any opportunities, will you keep an eye out for me?

On the flip side, if you never tell anyone what you really want, how can they help you get there? That’s where this question comes in. Whether your desire is to get a promotion, become a polished public speaker, get better at negotiation, or become a team lead, this question signals to your manager or mentor where you’d like to go, and asks them to help you connect the dots on opportunities that will help you get there faster.

10. Can you help me do X?

There are a few important things to keep in mind with your asks: 1) First, be as specific as possible. “Can you help me be a leader?” or “Can you help me with my project?” feels vague and hard to commit to. “Can I schedule 30 minutes on your calendar to practice delivering my presentation and get your feedback?” is easy to say yes to. 2) Second, make sure your ask is important to you. Do not waste your favors on things that don’t matter much to you. It’s not motivating for someone else to go out of your way to help you with a third or fourth tier priority. 3) Third, make your ask something that person is uniquely able to help you with. We all like to be playing to our strengths in how we spend our time. Especially if you are asking a favor of a boss or a superior, don’t give them requests that literally anyone else around you could help you do. Look for things that they can make a big difference on due to their unique skills, leverage, or relationships. “Can you help me get an introduction to X?” “Can you talk to Y [someone they have a good relationship with] and pitch the initiative I’m working on?” “Can you help me promote cause Z with a post/e-mail blast?”

If you found this article useful, you will probably find my new book, The Making of a Manager, useful as well. It’s an everything-you-need to know field guide to leading with confidence, whether you are a new manager, a seasoned manager, or someone interested in management down the road. You can order the book here.

Julie Zhuo

Written by

Product design VP @ Facebook. Author of The Making of a Manager https://amzn.to/2PRwCyW. Find me @joulee. I love people, words, and food.