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The 11 Questions I Ask in Informational Interviews

This article was originally published September 4, 2017.

I cannot tell you how many incredible opportunities informational interviews have opened up for me.

As someone in the beginning stages of her career, I am always looking to learn from those with more knowledge, connect with inspirational people, and challenge myself to grow in new ways. And I’m now frequently on the other side of the table, and am so thrilled to help others discover their careers and passions.

Informational interviews are not just for finding a job (although they are certainly helpful). Networking with someone new when you’re transitioning in your career, when you’re stuck, when you’ve moved to a new city, or simply because someone you’ve heard of seems really interesting all all fantastic reasons to learn from a new connection.

When I was a senior in college — discovering what I wanted to do, where I wanted to work, and how I was going to get there — I met a new person every week in my perspective field and picked their brain. I cannot thank them enough for their incredible generosity.

On my blog, I’ve taught you how to network from your couch, how to land a job when you’re not quite qualified, and how to make informational interviews fun. Needless to say, I have a lot of experience under my belt building these types of relationships.

5 Introductory Questions to Ask In Informational Interviews

1. What sorts of experiences have characterized your career journey?

Sometimes the greatest career turns are the ones you never could have expected (I talk about this in this episode of Women Killing It!).

Asking this in an informational interview can open you up to unexpected, exciting opportunities and leave you feeling inspired to embrace the curve balls life throws.

And remember, landing a job is just the first step in an incredibly unpredictable and exciting life-long path — embrace the ambiguity!

2. What does your day-to-day look like?

A perfect question for getting an insight into your interviewee’s typical job life and daily tasks.

If you’re looking at their field or company as a possible next step, you’ll get a great view of what life there might be like — fast paced, with new tasks every few hours? Or more consistent, with bigger projects that take time? It’s a great chance to discover if someone’s field is right for you.

3. How do you define success in your position?

Is it the number of clients? Traffic to a website? Implementing new projects? Being a compassionate team member? Seeing what constitutes success — both by company and their own standards — is key, as you’re able to see if it aligns with your values and where you see your future is heading.

4. What do you wish you knew at my age?

My all-time favorite question. Wisdom comes with experience, and if you’re speaking to someone older, chances are they have some great advice for how you can make the most of your youth (time is on your side!).

I’ve gotten some incredible answers that have allowed me to take risks, set goals, and have confidence moving forward.

If this person is the same age (or younger), a variation: “What do you wish you knew when you were in my similar position?”

5. Can you suggest the names of two or three other people I might contact for more information?

This question is actually the most important one you’ll ask during your entire interview. You’ll want to keep the conversation going with your interviewee. (Unfortunately, an informational interview is not a “one and done” experience, but instead the first step towards an awesome relationship.)

You also want to keep growing your network — who best to introduce you to another great resource than the person sitting in front of you!

6 Highly Valuable Questions To Ask In an Informational Interview

Informational interviews are no different than actual interviews in terms of weight-in fact, in my experience, I would say they are worth even more than an actual interview, and require just as much, if not more preparation, especially when you take into consideration the fact that the person you are having coffee (or a Skype chat) with has taken time out of his or her schedule to answer your questions

It is crucial that you do your research prior to the interview just as you would an actual interview. Keep the information about your career short and sweet; you are there to listen to what they have to say, not the other way around.

Avoid asking questions that you could have answered for yourself with a bit of research. If you are looking to switch industries, for example, you should know what the typical entry-level positions are within a particular field. Asking those sorts of questions is a waste of your (and your contact’s) time, and it doesn’t lend itself to a positive impression.

Use LinkedIn to ensure that you are asking questions that are customized to your contact’s career trajectory. Be aware of the position the individual currently holds and the responsibilities they have, as well as the previous positions they held. Knowing this information beforehand will allow you to maximize your time with the person.

Different people value different information, which is why there is no iron-clad list that proclaims itself as THE list to consult when conducting informational interviews. Here are 6 more questions that I’ve been asking in addition to those questions that yield valuable information (and why you should ask them)

1. What are the biggest challenges your company is currently facing?

I like this question because it gives you a sense of the kinds of challenges you would be facing in this role. Ask yourself if you can see yourself being excited to solve these problems.

This question also allows you to determine how you can use your skills and background to help the company overcome those challenges. Use that information to prove to the hiring manager (in your application materials) that you are not only capable of executing those responsibilities, but that your skills and background make you uniquely qualified to help the company, and that you are therefore indispensable. 

2. What are some qualities and skills that you think are necessary to succeed in this role?

Not everyone is as analytical as I am-I get that. But I think it’s important to know what sorts of qualities are key to success in particular roles so that you can measure how you stack up. This also shows you what skills you already have, and what skills you need to develop in order to be considered a competitive candidate.

3. How did you transition from (Role A) to (Role B)?

This is especially important if you are looking to switch industries. If possible, find a person who has made the switch you want to make, whether that’s from marketing to teaching, or vice versa. Knowing how they did it will give you a good idea of not only what kinds of jobs are out there, but also, what other resources are out there that you may be unaware of or underutilizing.

4. Is there anything you wish you had known prior to starting your career in (fill-in-the-blank) industry?

This question is, in my mind, one of the most important questions you can ask. In the past, I  have had informational interviews with people in certain positions where the answer to this question has shown me that I am not a good fit for a role in that particular industry.

While I would encourage you not to be dissuaded by a single person’s answer to this question if you are considering a particular field, this information is something important to consider, especially since these people are most likely working in the field you would like to transition into. 

5. Would you mind telling me about a recent project so I can get a better idea of what someone in (X Role) does?

Asking your contact about recent projects they have completed will help you get a sense of the sorts of things people in that position do, and more importantly, gauge for yourself whether or not you would enjoy them.

Be wary however, that depending on the field, some people may be wary of disclosing this information due to privacy reasons. If that’s the case, ask them what a typical work day looks like for them. This question will help you understand what a typical environment in your dream company looks like.

6. How do you see (X industry) developing in the future? How is (X industry) changing?

This question gives you a lot of insight into the future of an industry. Having this information before you embark on a potentially new career path will help you make the most informed decisions possible. It also gives you insight into skills you might need to develop in order to be competitive.

I promise: as scary as they may be, informational interviews are one of the easiest things you can do for your career.

While this list isn’t exhaustive, these questions do yield a lot of valuable information for those of you who are seeking new jobs. These interviews are a simple thing that you can do to help develop contacts in your industry (or company) of choice, and make the most informed decision possible in regard to your career. 

And remember, this person is being extremely generous with their time and resources — buy their coffee and sincerely thank them; and then keep in touch.

About the Author

Tori Dunlap

Tori Dunlap is an award-winning digital marketer, blogger, and entrepreneur. Founder of victori media, helping 20-somethings live life victoriously. Obsessed with finding cheap flights, reading a good book in the bathtub, and you.