10 Questions to Ask People at the Top of Their Game

Use these tips to get successful people to part with their knowledge.

10 Questions to Ask People at the Top of Their Game

Learn from the career highs (and lows) of others.

One great way to learn how to succeed is to hear how other people did it and follow their leads. So if you ever got to pick the brain of Warren Buffett, Shonda Rhimes, or Megan Rapinoe, do you know what you’d ask? Don’t lie; some of you already do, and that’s great. When it comes to formulating good questions to ask people you admire, the rest of you are likely going to wing it.

Career tip: Don't ever wing it. You may not ever meet a red-carpet superstar, but your chances of bumping into someone whose career path you'd like to follow—at a networking event, in the grocery store, or maybe even in an elevator—are considerably higher.

When that happens, take advantage of it. People who have risen to the top of their field are often more than happy to talk about how they got there. After all, everyone likes their hard work to be recognized, (plus, people like to talk about themselves). Ask successful people one or two of these questions to get some of their best insights and advice.

10 questions to ask people you admire

1. When did you consider yourself a success?

Success to you may not be the same as success to someone else. Not only can this question yield great insight into others’ values and priorities, but it can also open your own mind. Having a broader definition of success is a great way to conceive of additional opportunities to experience it.  

2. What advice would you give to someone starting out?

Sure, some people started out with more of an advantage than others, but plenty of successful people began their career with little more than the metaphorical nuts and bolts. Often those early years of trial and error yield invaluable lessons.

3. How do you push through your worst times?

Pain points are good sources of questions to ask people. Life is rarely a cakewalk for anyone who adheres to high standards. Asking someone how they persevered through the rough patches can motivate you to keep putting one foot in front of the other, especially when the journey seems never-ending.

Beyond that, their answer can also give you practical, concrete advice for getting out of a rut. Nothing beats the wisdom of someone with experience.

4. What keeps you awake at night?

People can be kept awake either with worry about something bad or excitement for new opportunities. It’s a solid question to ask someone because successful people are often focusing not only on the present but also on the future. This can give you a sneak peek into industry trends and challenges in the marketplace.

5. What are your success habits?

Ask successful people about their daily routines, and you’ll learn about the habits and steps that help create an environment of success. This question typically reveals things anyone can do as long as they focus and follow through to meet their goals.

6. What personality trait should every leader have?

Yes, the trait they mention is probably of value and you should develop it as part of your skill set, but this question is a bit more revealing that it appears. You think you’re asking about leadership qualities, but the person will likely hear an opportunity to talk about themselves—remember, people love to talk about themselves. Listen closely. What trait do they perceive themselves to have? Does their reputation back that up? Remember this when you reach the top of the ladder.

7. Whose career inspires you and why?

Just as you admire this person’s career and skill set, they for sure admire someone else. Finding out who that is and what makes them special can point you to another source of inspiration.

8. What was the last good book you read?

You can never have too much fodder for your brain, especially if it comes recommended by an esteemed source. You could also ask what they’re reading now, though you risk putting them in an awkward position if they don’t happen to be reading anything at the moment—these are busy people, after all.

9. If you weren’t a [job title], what career would you like to explore?

This is a better question to ask people than the standard, “If you could have any job in the world, what would it be?” The reason? Successful people are almost guaranteed to tell you they are doing the job they always dreamed of. Finding out what other types of careers pique their interest can reveal the root source of their career satisfaction—and make you evaluate your own—whether that’s doing something nobody has yet done (“I’d be an astronaut and be the first person go to Mars”), giving back to their community (“I’d be a teacher”), or fame and recognition (“I’d be a movie star”).

10. Are you hiring?

You never know. People at the top often admire the “go big or go home” play.

Yes, it's one of the weirder questions to ask people...

...but nobody is just going to offer you a job. You have to let them know you're looking. Could you use some help getting the word out? Monster's got a large network of recruiters who search the site every day in the hopes of finding talent just like yourself. Get started for free by uploading up to five versions of your cover letter and resume. You can also get job alerts sent to your inbox so you’ll be on the frontline of applicants. Start writing your success story today.