actually useful questions to ask in informational interviews

A reader writes:

You’ve written before about how NOT to behave in an informational interview (i.e. use it to try to get a job), but I wonder what you recommend to get the most out of them when you’re approaching the meeting with the proper mindset.

I’m about six months away from getting a masters degree, and another student in my program recently arranged for me to have lunch with her and a family friend. She organized the lunch because the family friend works in an industry related to the particular niche of our field I’d like to work in. This was an incredibly kind thing of her to do, but it was rather short notice, and I scrambled to come up with questions.

I asked a few specific things about the direction the industry is going in, and a few questions about a new side project her company has that’s of particular interest to me, but I fear that beyond that she was left to lead the conversation more than I would have liked. She did so wonderfully, giving us a tour of the building, asking me about myself, showing me the software she uses, etc. I wonder though, how I might have made more of this networking opportunity. Obviously some questions are specific to industry and situation, but do you have any across-the-board recommendations (beyond being prepared) for making the most of informational interviews, particularly ones you didn’t seek out?

Like with asking questions in interviews, my advice on this is to spend some time really thinking about what you genuinely want to know from this person who has experience in your field. That’s probably going to lead you to questions I’d never think of, like or “how do you handle the frustration of X?” or “how have the new regulations on Y played out in your work?”

In other words, don’t just focus on being impressive (which is the pitfall a lot of people fall into), but think seriously about what you’re really wondering about. I can promise you that this person doesn’t want to spend their time answering questions that you’re asking because you saw a list that suggested asking them; they want to answer the stuff you’re really dying to know. (I’m not saying that’s where you’re coming from — I just see it so much that I need to raise it.)

Now that that disclaimer is out there, here are some questions that I think are great to ask in informational interviews:

  • What do you wish you’d known about the field before starting in it? Do you think there are common misperceptions people have about this work as they’re looking to get into it?
  • What types of people do you think really succeed in this field? What types have more trouble?
  • One thing I’m worried about is ___. Do you think that has any merit?
  • Do you have thoughts on the best things I can do to stay current in the field — things to read, organizations to join, people to talk to?
  • Who do you feel are the best employers in the field? Why? Are there any you’d caution me to stay away from?
  • Are you able to give me a sense of what kind of starting salaries you see for roles like X and Y?
  • What are your/most people’s hours like? Are you able to leave work behind when you leave, or do you need to stay pretty connected in the evenings and on weekends?
  • Anything you see job candidates around my level doing that you think really hurts them? Or that you wish people would do differently?
  • Can I tell you a little about my background and experience so far, and see if you have any suggestions for things I might do to strengthen myself as a candidate?
  • Do you think I’m being realistic about the roles I’m aiming for in this next step?

What other suggestions do people have?

{ 44 comments… read them below }

  1. Eric*

    I think a question about what differentiates the different employers in the field would be useful. For example, in my industry, some firms hire entry level people and train them and move them up through the ranks. Other companies expect entry level people to leave within a couple years for something else. Knowing this as a differentiators prior to interviewing at the companies would have been useful, but I didn’t know what I didn’t know.
    I imagine the differences working between working at a big company versus a small one is industry dependent. Having someone go through the pluses and minuses of each within your industry could be useful.

    1. Bernease Herman*

      Wow. I’ve done plenty of informational interviews, but this is the best question I’ve heard! Something most people would want to know.

  2. AVP*

    This is really interesting…recently I was connected with a much older, successful woman in my field (we went to the same high school and were connected by the alumni coordinator; we are in a very small niche field). She seemed a little befuddled by my small talk and clearly didn’t want her time wasted (who does?) so I just flat out asked her what was on my mind, and what I was struggling with that week – how did she handle her career/work/life/family balance in a field thats known for demanding a lot? Once she realized I was trying to work through a legitimate concern, and not just to “network,” she really opened up and we’ve had a really interesting back-and-forth. So I guess my unsolicited advice would be, echoing Alison, use it an an opportunity to prepare and ask the kinds of questions you’d love to ask a mentor or a boss but don’t get the opportunity to, or can’t because your relationship dictates otherwise.

  3. ZSD*

    Several years ago, I did a couple informational interviews with paralegals (and gained the valuable information that I do not want to be a paralegal). One thing I’m glad I asked them was whether they got to do interesting, analytical legal work, or if they were just making copies and stamping signatures. I wasn’t sure how much of the brain-work was reserved for lawyers.
    What I learned is that if you work for a large law firm, you’ll mostly be doing comparatively mindless tasks, but you’ll make a lot of money. Conversely, if you work for a smaller law firm with only one or two lawyers, you won’t make nearly as much, but you might be trusted with substantive research and writing work. This is a trade-off I would never have thought about, and it was incredibly helpful to have this information!
    (Note that this tradeoff is just what I was told, not something I know first-hand; paralegal AAM readers are welcome to correct me if I’m wrong!)

    1. Bwmn*

      Another note about big firm vs small firm can also definitely be informative in regards to when during a career it’s helpful. I work as a fundraiser in nonprofits – and the differences between a big/small organization can be huge. It’s a similar dynamic of being in a small place and getting your hands involved in everything whereas in a larger organization you end up becoming more specialized.

      I think the specific dynamics of big place/small place will vary from field to field – but it’s good to get insight on.

      1. ThursdaysGeek*

        Interestingly enough, I avoided a large local employer for many years specifically because of that: I liked doing lots of different things and didn’t want to end up too specialized. Then, when I did end up at that company, I was in a job that had all sorts of variety and fit me very well.

        1. Bwmn*

          In regards to fundraising – I personally believe there is a lot of value being either the only or one of the only people. In addition to doing a bit of everything, you also get the chance to do a to more networking and are invited to events that in larger organizations is far more rare. Also, when you’re in a small team it’s far easier to say “I was in charge of bringing in X/renewing Y” – in a big team, claiming ownership of a relationship is far harder.

          1. Well*

            Really great point. Also a fundraiser, and hadn’t really considered that particular framing, but you’re absolutely right.

            I do think there are some advantages to working at a larger organization is the opportunity to work on many different programs/issue areas. Small orgs are typically more specialized in terms of services provided. When I transitioned from a small org to a larger one, I also had to very quickly get up to speed on navigating internal bureaucracy. I am now much, much better at generating buy-in for my own ideas, and building (internal) relationships to Get Things Done when I need it. (I also think there’s a sense of professionalization that comes with larger orgs that’s helpful to have some experience with – small nonprofits are sometimes run somewhat haphazardly, in my experience; and while not all large nonprofits are run *well*, the additional of full-time HR people, specialized staff, management with greater experience, etc. tends to help mitigate that somewhat.)

            I really value my experience at small orgs for the reasons you mentioned – especially early in my career, it really made a difference in terms of giving me lots of responsibility (probably far more than I really ought to have had!). But my time at larger orgs has been valuable, too.

  4. The Cosmic Avenger*

    I would say that for a grad student I might not expect a lot of questions, as they may have never had a full-time and/or non-retail job before, so I would probably try to run it as a bit more of a show-and-tell about my job and my area, as opposed to the way I would approach an informational interview with someone who is closer to a colleague, where I would expect them to guide the topic(s) covered, as AVP did above.

    1. Isa*

      I would just caution you about making that assumption about grad students and experience. A great many of them may be seasoned professionals in their 30s+.

  5. Joey*

    where do folks go when they leave this niche field?
    Why do you think they leave?
    Where do you think this field is heading?
    What can I expect in terms of what it takes to progress in this field?

    1. College Career Counselor*

      Along those lines, I would suggest “What’s the most fulfilling part of working in this firm/industry?” and “What do you feel is the most challenging aspect day to day or long-term?” If someone said to me, “oh, I absolutely love all the event management projects that are part of my job!” I would count that as good information and look for another line of work. You do have to know something about your own skills, interests, and temperament so you can evaluate the response you get against your own desires and norms. We just had that yesterday in the “should I work for the government” question. A lot of those answers were couched in terms of the respondent’s preferences.

      Another question I would consider asking (if the conversation has gone well) is “Is there anyone else that you recommend I talk to about this field?” I think it’s important to talk to multiple people in the field to see where are the areas of consensus, as well as the outliers. Here’s an example from the academic world: Professor Z might blithely encourage going to graduate school for any half-way bright, interested student. But Professors A, B and X might have a much more nuanced conversation about the challenges, costs and employment outlook.

  6. Stephanie*

    Good rule of thumb for determining if a question is good is to ask myself if a high school student could have asked it. Granted, a lot of times I am going into informational interviews with only a basic amount of info, but I find asking that helps me to come up with more specific questions and do background research.

    Also…I know there are some very precocious high school students who read here. It’s really more shorthand for “Am I asking a question that sounds like I did some basic research before talking to this person?”

  7. Mimmy*

    This is INCREDIBLY helpful. Not knowing what to ask has been a big challenge for me. There have been a couple of people I’ve wanted to contact for quite sometime, but I haven’t been able to bring myself to initiate the conversations for this very reason. Whenever I do get to talk to someone, most times I end up just getting more contacts.

  8. misspiggy*

    All great questions. One more could be, ‘What have you worked on that left you feeling really satisfied or pleased with the outcome? ‘

  9. TOC*

    When I was searching for my first “real” job in my field, I did several informational interviews. I usually asked the other person for a little bit of information about how they ended up in their job role and what their work was like day-to-day. But the other burning question I had was about the paradox of entry-level jobs in the field seeming to require experience that I as an entry-level person just didn’t have. It was 2009, so many entry-level jobs were going to people already working in the field.

    I asked questions like, “How else can I be gaining experience in this field and best highlighting the experience I already have? Does volunteering count as experience in these employers’ eyes?” “What are employers in this field looking for in entry-level candidates?” “What kinds of job titles and salary should I be anticipating at my level?”

    1. ZSD*

      I think these are good as long as you’re talking to someone with hiring authority/experience, so one might want to make sure that the interviewee has that experience before asking these questions.
      For example, I’ve never sat on a hiring committee or even reviewed resumes, so if someone asked me what people in my office were looking for in entry-level candidates, I wouldn’t really be able to give a valid answer. Worse, some people who don’t have this experience might be inclined to *guess* at the answer, and then the interviewer might end up with wrong information.
      But I think these are exactly the right questions to be asking people who’ve hired people recently.

  10. C Average*

    Basically, when you’re learning about someone’s job, your first order of business (which is pretty straightforward) is to get the answer to “how do you do your job?” Most people interpret the “you” here as “someone in your role,” and give you a rundown of the job description.

    Then you go into, “no, how do YOU do your job?” which tends to be a lot more informative and useful, because it’s about what that individual brings to the role that’s unique.

    A few things that I find fun to ask about that get to the meat of “how do YOU do your job:”

    –on an average day, what tools and windows are always open and frequently in use on your computer?
    –how have your past roles influenced how you perform your current role? what’s the sort of narrative arc of your career?
    –which other teams, departments, external partners, etc., do you work with often?
    –what are some tasks you tend to delegate or outsource rather than do yourself, and how are different tasks allocated on your team? (I especially like this one because, if you ARE angling for a job, it tells you what kind of work this person would prefer to offload. If you’re good at that kind of work, you might be able to mention it in passing.)
    –what are your team’s dynamics? Do you tend to collaborate or work separately? Do you all share a similar workload, or does everyone specialize?
    –what kinds of ongoing learning do you need to do in your role? Is it self-directed, or are there structured learning opportunities in place?

    1. C Average*

      One quick note: I usually do informationals with people from teams I’m likely to work with in my existing role, so it’s strategic, but not in a job-hunting sense.

  11. yup*

    I love the idea behind this post. I think Allison’s advice is spot on. Take a moment to put your thoughts in writing about what you REALLY want to know about YOUR FUTURE PROFESSION. I think you’ll be amazed at what you came up with

  12. LisaS*

    I always encourage my students to ask “Are you on your Plan A, or did you take a different route into your job/career?” It’s really interesting to see how people see their own career trajectories and, because the conversations frequently touch on transferable skills (“Well, I found I was really good at X so I leveraged it into A-based X…”), they’re of particular use to students.

  13. dragonzflame*

    Mine was, “where do you see the industry being in the next 10-20 years?” To be fair, I’m transitioning into an industry that many claim is dying, but the people I spoke to all seemed to think it was more a case of changing opportunities.

    Another one you might want to think about is asking about any professional associations – some are more worthwhile than others and it’s good to get some intel on whether they’re worth it before paying to join, even as a student!

  14. Tiffany Youngblood*

    I’ve done a number of informational interviews with people for a blog I started a few months ago, plus some just for my own benefit. Preparation is definitely key. I’ve got a database of questions that I can always refer too if needed, but I try to at least come up with 2-3 new questions for each interview. For purposes of my blog, I never have more than 5 or 6 questions total, but that’s primarily because I don’t want to spend time transcribing an interview that goes any longer than 15 minutes or so.

    The first question I always ask (after getting background info) is why they work in the industry that they are in. (In my case, why nonprofit work?). This isn’t going to give you a ton of beneficial information, but I think it’s interesting to know why people do what they do and it sets a nice tone for the rest of the interview.

    The other thing I always ask, at the very end, is “what do you know now that you wish you had known at the beginning of your career?” It’s similar to the first question Alison mentioned, but I’ve asked everyone from the CEO of the largest nonprofit organization in the world to people just now starting their careers. For whatever reason, it’s a question that seems to throw people for a moment, but I’ve gotten really good results with it. Just be prepared for them to take a minute or two to figure out their answer.

    1. Tiffany Youngblood*

      A couple others:

      If the person your interviewing has set aside a decent amount of time for the interview (sometimes you get 15 minutes, sometimes you get an hour or more), and there’s opportunity to talk about what you’ve been doing up until that point, I like to ask “Based on what you know of my experience and skills so far, what do you think I need to focus on in the near future to be better prepared for a career in this industry?” This won’t always be possible to ask, but if you think it fits with the conversation you’ve had, go for it. You’ll probably get a response that gives you something you hadn’t even thought about needing to know.

      Other than that, ask about trends in the industry and/or the area. For example, I interviewed someone who worked at a nonprofit in Chicago that was focused on education and at-risk youth, and I asked them “What do you think is the biggest concern when it comes to the public education system in Chicago? What is most promising about it? What’s the biggest stereotype?” I think it’s important to not just focus on skills needed or the positive aspects of that career, but what the biggest challenges and such are. You want to come out of the interview with a more all-around understanding of the industry you want to be in.

  15. ZSD*

    I think the first question on Alison’s list is a great one. I think we all have the tendency to romanticize the industries we think we want to get into, particularly if they’re industries we’ve dreamed of entering for a long time*, and it’s good to have someone tell us how different things are when you actually work in that industry.

    *Like, say, having wanted to go into publishing ever since reading _Just as Long as We’re Together_ in middle school – speaking purely hypothetically, of course. :)

  16. TheLazyB*

    Best. Timing. Ever. I have an informational interview tomorrow :) The lady in question is retired, but will have an excellent overview of the field I want to get into. These questions are great! THank you – both Alison and commenters!

  17. Student*

    What skills/abilities do you need to excel in this field?
    Are there any cross-disciplinary skills that are valuable but not common in this field? (programming, mathematics, specific language fluency, …)
    What metric do you use to determine whether experienced people are doing well in this field? (number of research papers, sales numbers, membership in committees, number of staff managed, …)

  18. OP*

    Alison and commenters, these are great suggestions! Looking back at my conversation, a lot of what’s been mentioned here came up naturally without me really having planned it. I feel a little better now about making the most of the opportunity. I don’t think the woman I spoke with does much hiring, but I’ll definitely keep these two in my back pocket for the future:

    “Can I tell you a little about my background and experience so far, and see if you have any suggestions for things I might do to strengthen myself as a candidate?”

    “Do you think I’m being realistic about the roles I’m aiming for in this next step?”

    I live in a city where internships in my field are readily available, but paid jobs less so. So learning what kind of experience I should be seeking out as I make use of my last few months as a student would actually be very valuable information.

    Alison, thanks for answering my question! I’m the kind of person who’s a little uncomfortable with widening my network, so I want to be sure that I’m networking well and not wasting the time put in outside of my comfort zone. Not to mention being respectful of the person who’s interrupted her day to speak with me.

    1. TCO*

      From your letter it doesn’t really sound like you botched things like you think you did. You had a natural conversation and learned a lot. It sounds like your interviewee enjoyed speaking with you. She probably wasn’t surprised that you didn’t have an exhaustive list of probing questions–few people do, especially those just starting in their careers. As long as you sent her a thank-you note/email you did just fine. :)

  19. Lee*

    I recently moved to a new state, and have several years experience in a fast-changing and rumored-to-be struggling industry. There are a couple of places nearby that I would love to work, they do the kind of work I am really interested in. Would it be appropriate to set up informational interviews? I’d like to ask how they stay relevant, and what organizations in the area are hiring, what subset of work is available locally, etc. I really enjoy the work I do, and want to keep doing it.

    1. Tiffany Youngblood*

      I think it’s absolutely appropriate to ask. I wouldn’t necessarily just randomly reach out, but see if you can’t figure out the name of someone who has a role you’d be interested in having and reach out to them specifically. I’ve always had better luck and better interviews that way, versus just contacting the HR department.

  20. Ajax*

    What is a typical day like? What do you do day to day?
    What are the backgrounds of the people you’ve hired/people on the team? What kinds of people have excelled in role X?
    What is the career path for someone who stays at this company?
    What software do you use? (If relevant & non-obvious.) What software/skills are most important in this field? What training do employees get?

    1. Ajax*

      ETA: As you can tell from my suggestions, I think there’s some overlap with the sort of questions you’d ask at the end of a regular interview.

  21. Wanna-Alp*

    Not sure how to ask questions about this one, but diversity is a thing in my field (as in, the lack of it, and the lack of a supportive culture), and if you’re a member of a disadvantaged group, it seems like a really useful thing to be able to ask about, both for the field in general and in a specific workplace.

  22. OriginalEmma*

    Thanks for these. I will be talking to some alumni in a few weeks, so I think I’ll use these questions to guide the advice (jeez, am I really competent enough to give that?!) I provide or stories I tell.

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