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

“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?

Virginia Woolf once said, “Without self awareness we are as babies in the cradle.” Self-awareness is understanding the extent to which your own perceptions of yourself — what you’re good at, what your growth areas are, how you’re progressing and learning — matches reality and what everyone else thinks. Most of the time, a gap exists due to well-documented human biases that tell us we’re better at certain things than we actually are, or due to our scathing internal critic that can be much harder on ourselves than others.

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?

If you’re feeling a puff of pride about how you knocked that last project out of the park, or how you’re firing on all cylinders, it’s time to unveil this little question and present it to your manager, or another senior supervisor who knows your work.

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?

“We all have blind spots, and it’s shaped exactly like us,” author Junot Diaz said. Maybe your nature is to be conservative and shoot down the big, bold ideas. Maybe you have an unchecked habit of interrupting others. Maybe you don’t realize when you ramble.

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?

If you’re looking for a classic conversation starter that avoids any pontification on the weather, feels engaging rather than cheesy, and leaves you learning something new, look no further than this question.

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?

Time is the most precious resource we have, and pretty much all of us don’t feel like we have enough of it. Learning how to prioritize effectively — how to choose the most rewarding or leveraged actions with that limited time — takes a lifetime to master, and chances are good that hearing the tactics of how others prioritize will help you in your own day-to-day.

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?

This is a tweak on question #4, except instead of asking about what’s hard, you’re asking for a non-obvious nugget of wisdom. This question will net you everything from early-stage trends and insider knowledge to hilarious behind-the-scenes stories. At its best, the answers to this question stay memorably with you for weeks, months, or even years. Be aware that this question works better for people with jobs that you know less about — it can feel like a hard question if you pose it to someone who does the same thing as you because of the pressure to come up with something novel.

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

Mentorship is something all of us hear we should seek in order to grow and advance. And yet, Sheryl Sandberg in Lean In cautions against asking people directly “Will you be my mentor?” It feels like a loaded question, like you’re asking the person to take on a formal and heavyweight responsibility. Instead, use this lightweight question with those you admire. It’s both authentic praise that the recipient will appreciate, as well as an opportunity for you to learn something from an expert. And that’s exactly how the best mentorship relationships start — from a curiosity to learn and a willingness to teach.

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

If you have some spare cycles on your hands and you’re looking for ways to increase your impact, this question is exactly what you need. I’ve never felt anything but gratitude and admiration for someone who has asked me how they can help with one of my biggest problems. It leaves me with the impression that the asker is proactive, thoughtful, and a great team player. On the flip side, asking this question often of your manager or peers will net you additional opportunities to stretch and grow that you might not otherwise have gotten. Even if the answer at the moment is “Thanks, but there’s nothing you can help with right now,” your initiative will be remembered and rewarded when future opportunities arise.

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?

I always tell people who aspire for leadership opportunities that the biggest mistake they can make is keeping their aspirations a secret. It’s natural to do so, because revealing your dreams to someone else can feel like exposing a vulnerability (for example, they might see you as a failure if you don’t achieve it!)

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?

Think back to the last time you asked someone in senior position to do you a favor. For most people, the examples are few and far in between. Why? Because we don’t want to impose and be seen as a burden. And yet, making direct asks of other is one of the most powerful things you can do to achieve your goals. I often encourage my reports to make bolder asks of me. The answer won’t always be yes, but you’ll get more than if you never ask.

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.

Currently: Inspirit. Former Product Design VP @ FB. Author of The Making of a Manager https://amzn.to/2PRwCyW. Find me @joulee. I love people, words, and food.

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