Job Shadowing Questions to Ask

Anita Bruzzese
by Anita Bruzzese   Career Advice Expert 

Job shadowing might sound a little creepy—does it mean you’re skulking around a workplace, spying on people? Well, part of that is correct—you will be in a workplace and there will be people. But far from skulking or spying, you’re given a front-row seat to how work gets done.

Whether it’s in an architecture firm, at a high-tech startup, or at an auto body repair shop, experienced workers let you watch how they do their jobs. You’re given a chance to ask job shadowing questions, observe a “day in the life of,” and just absorb and reflect on whether the environment and the workers are something that appeal to you.

Some job shadowers will come away from the experience saying, “I love it! This is what I want to do with my life!” while others may say, “No way. Not what I expected and not for me.”

Either way, the only way you’ll really get the most from the experience is by being prepared, which includes coming up with job shadowing questions. Do your homework on the career you’re angling for (as well as the industry) before your visit, and then come up with job shadowing questions that you believe will help fill in the blanks for you—things you can’t gain by looking them up online or reading about them in a book.

First, you need to get a job shadowing opportunity. Research companies in your area that interest you. Or, approach your high school or college career counselors and ask them if they can help you arrange a job shadowing day—many schools maintain contacts in the business community for just this purpose.

If you don’t have a school to help you, it’s OK to send a letter to a company’s human resources department making your request and stating why you chose the company. You can say something like, “I’m very interested in architecture, and I would love the opportunity to job shadow someone at your company, to see what it’s like to be in the industry.”

Tell them you don’t want a lot of time—perhaps a day or half a day, and that you’ll follow up with an email or phone call in about a week. This gives the company time to locate someone who will let you tag along for a day.

Whether it’s in an architecture firm, at a high-tech startup, or at an auto body repair shop, experienced workers let you watch how they do their jobs. You’re given a chance to ask job shadowing questions, observe a “day in the life of,” and just absorb and reflect on whether the environment and the workers are something that appeal to you.

If you have an inside contact at a company you’d like to job shadow at, or perhaps a particular employee you’d like to shadow, follow the same protocol that is laid out above—make your request, state your reason, and note that you’re only looking for one day or half-day for shadowing. Your inside contact/particular employee will likely have to get an official seal of approval for your request.

Be patient, and note when you plan to follow up. If the contact/employee notes when they’ll get back to you, wait for them to get back to you. If the day comes and goes and you don’t hear anything, politely inquire about the status of your job shadow request.

If your job shadow request is approved, you need to approach it like a job interview (this is also a benefit to job shadowing—it provides some interview practice) and think about what job shadowing questions you want to ask (more on this soon). Dress neatly—clean and unwrinkled clothes, combed hair, and shoes in clean, unscuffed shape.

A good option is dress pants and a dress shirt, or a skirt and a dress shirt. Bring along a notebook and pen to take notes on the answers provided to your job shadowing questions. When meeting others (especially the person you’ll job shadow!), always make eye contact and offer a firm handshake.

Your primary goal when job shadowing is to observe. Stay alert and interested, mind your manners, and in addition to writing down answers to your job shadowing questions, write down observations that are of particular interest to you!
Now, on to the subject of job shadowing questions. Below is a list of some common questions to consider asking. By no means do you need to ask all of these questions, but do have some prepared to ask so that you can get as much as possible out of the experience.

Job shadowing questions

  • What type of education and training prepared you for this career field?
  • What type of education and training would you recommend for someone just starting out in this career? For someone who wants a job title like yours?
  • What types of skills are necessary for succeeding in this career?
  • How has this career field changed since you started?
  • How did you know this was the right career for you?
  • What makes you excited about your job?
  • What other careers or industries could you work in with your education and experience?
  • What do you see as the biggest changes that have happened in this career field? That will happen in the future?
  • How has technology changed this career? What kind of technology do you use to do your job? What’s the most common technology used in this industry?
  • How has the state of the economy affected this career?
  • How long have you worked for this employer?
  • How did you choose this employer to work for?
  • How does your employer differ from its competitors?
  • How did you get your current job?
  • What is your exact job title, and how long have you been in the job?
  • What do you like most about working for this employer?
  • Have you worked for any other employers?
  • What do you like most about your job?
  • What do you like least about your job? (Tread carefully and gingerly when asking this question.)
  • Can you describe a typical day at your job?
  • How much of your day is spent behind a desk? Out in the field?
  • How much are you required to work outside normal business hours?
  • What are some of the biggest challenges you face in your job?
  • How is your work-life balance with your job?
  • What’s the most valuable reward you’ve reaped from this job?
  • What’s the most valuable lesson you’ve learned in this job?
  • What advice do you have for someone considering this career?
  • What types of summer jobs or internships should I seek out as I continue my education?
  • What websites and tools do you use to stay current with your career and your profession?
  • What’s the biggest stumbling block you see with younger jobseekers?
  • What does your employer—or employers in general in this field—look for in younger jobseekers?
  • Do you expect the workplace to change much in the next five years?
  • What is the employment outlook for this career field? How much demand is there for entry-level jobseekers?
  • Is there anything else that I have not seen today, or that we have not talked about, that you think is important for me to know as I continue my quest for the ideal career?

When your job shadowing experience wraps up, be sure to procure contact information from the employee you shadowed (in case any additional questions come to mind once you arrive home). Be sure to thank the employee for their time and input. And if you arranged the job shadow through someone in HR, be sure to thank that person for their help. Best of luck!

Know that when it comes time to apply for jobs, you’ll need a resume and cover letter that must be customized to every job advertisement your respond to. Check the plethora of resources that LiveCareer offers on resume and cover letter writing, and make sure your documents stack up!

About the Author

Career Advice Expert

Anita Bruzzese Career Advice Expert

Anita Bruzzese is an award-winning journalist with more than 25 years of experience, writing for such publications as USA Today, Shape Magazine, and Mashable. She is also the author of two career advice books, and has appeared on The Today Show as a career expert. Anita has been interviewed for O, The Oprah Magazine, Glamour, Cosmopolitan and Huffington Post. Visit her website at


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