9 Questions You Should Ask In An Informational Interview

Sorry, career advisers of the world, but asking for an informational interview is one of the most awkward tasks of your adult life.
Yes, yes, we know these “casual” conversations with the people who work at our dream companies or hold our dream jobs are a great way to get our foot in the door, and maybe even find out about openings before they're listed on job-search boards. Still, composing the email asking to meet? We'd rank it up there with telling someone you just want to be friends.
But maybe this will help: As someone who's actually given a few informational interviews in my time, I can tell you the good ones are rewarding for both parties. While the interviewer got to find out the secret details of how my workplace ran and what kind of paths they might take in a field like mine, I got to see my job through fresh eyes. And talk about myself.
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"Most people’s favorite topics of conversation revolve around their own lives," career coach Elana Konstant tells Refinery29. (Ouch?)
My point is, if you make a good impression and ask the right kinds of questions in an informational interview, it's going to be a win-win.
"It's not schmoozing if you actually enjoy the conversation that you're having with someone," says A-J Aronstein, associate dean at Barnard College's Beyond Barnard office. "If you make a genuine connection with someone, you're helping HR by connecting to someone in a firm. You're making it easier for them to say, 'Oh, we've identified someone who's A) got really good qualifications, and B) already knows us and is interested in coming here.'"
So reach out to your would-be connections on LinkedIn, search through your other real and virtual networks, and ask the questions we've gathered here.
1 of 10

"Do you have half an hour to tell me about your career arc?"

Do you have half an hour to tell me about your career arc?



This is how Aronstein suggests you phrase your message on LinkedIn or email. Don't send your résumé or ask for a job. All you're doing is asking for a casual conversation over email or phone.

"It's really hard to ask — the activation energy can be very high," Aronstein says. "But once you've got a couple of responses, it starts to feel really good."
2 of 10

"What are the priorities and challenges you anticipate for this industry?"

What are the priorities and challenges you anticipate for this industry?



"Before going into an informational interview, job seekers should prepare by researching the interview subjects and their employers," Konstant says. That research will help you ask detailed questions that show you're serious about this field. But don't go overboard and show off how much you know already. That's not why you're there.

"Make sure you are listening more than you're talking," Konstant adds.
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3 of 10

"What is your typical day like?"

What is your typical day like?



This may sound like a generic question, but it's also a chance to let your interviewees talk about their favorite subject, themselves. While they do that, you'll gain insight into whether this is a job you really want to have one day. Think of this as the behind-the-scenes tour you won't get from human resources.
4 of 10

"What do you find most surprising about working for this company (or in this industry)?"

What do you find most surprising about working for this company (or in this industry)?



You're not seeking out dirt here, but you can get a fuller picture of the job that may either light a fire under your butt to go out and get it, or lead you in a different direction than you'd expect.

"A job seeker might be more comfortable asking frank and candid questions from someone in this adviser role than from someone who is deciding on her future employment," Konstant says.
5 of 10

"What's the advice you wish you had when you were sitting in my seat?"

What's the advice you wish you had when you were sitting in my seat?



"People love giving war stories," Aronstein says. You might even ask them to tell you about the biggest mistake they made at the start of their career.
6 of 10

"What are the qualities you think employers are seeking in this industry/company/role?”

What are the qualities you think employers are seeking in this industry/company/role?



Though you should let the conversation flow naturally, you do also want to get a few hard facts to be able to use in your job search. If there's something you're missing that could give you a leg up, you need to know sooner rather than later.
7 of 10

"Can you recommend another person in this space I should speak to?"

Can you recommend another person in this space I should speak to?



Networking is not just about getting in touch with one person, but about reaching beyond to that person's people. Maybe your interviewee can't hire you, but they might know someone else who can.
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8 of 10

"Can you look at my résumé and tell me if there are any red flags?"

Can you look at my résumé and tell me if there are any red flags?



Once you've established a rapport with your interviewee, you can try to take things to the next level.

"It's important for every informational interview to end with a specific ask, and you need to have an idea of what that ask could be before you go in," Aronstein says.

Not only is this editing question a good excuse to get that document in the right hands, this is an opportunity to find out if you've chosen a résumé format that's looked down upon in this industry, or if there are valuable keywords you should add.
9 of 10

"Can you take a look at my cover letter and give me some pointers?"

Can you take a look at my cover letter and give me some pointers?



There is no single way to write a cover letter. The structure and content varies from industry to industry, so use this informational interview to your advantage and ask what kind of cover letters stand out in your particular industry. Plus, it's always great to have a pair of seasoned eyes look at your writing to catch any spelling mistakes or awkward phrasing.
10 of 10

"Can I mention you in my cover letter?" "Can you recommend me for the job that’s open here?"

Can I mention you in my cover letter?



Mentioning an employee's name in a cover letter is often a good way to get your application seen by a hiring manager. If this conversation has gone well, the interviewee shouldn't feel like this is a big ask. On the other hand, if you're still feeling awkward about it, this might be something you can ask later on in a follow-up email.

"If someone has a strong rapport with an informational interview subject and there is an opening at her company, then it's perfectly acceptable to follow up and ask about the position," Konstant says. "I would suggest couching it more as wanting to get her/his insight into the role before applying, which will hopefully lead to an offer to refer the application."

Even if there's no job opening at the moment, Aronstein suggests making it clear that you might be in touch again.

"Set the expectation that something else is going to happen, and that will make it clear to the person how you expect to interact going forward," he says.

Also, don't forget to send that thank-you email!
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