No problem!  This stuff is so weird and alarming, right?  The skill set to find and land a job is totally different from the skillset to do the job, but there’s a general lack of acknowledgement about this fact, which leaves most of us floating around feeling stressed and inadequate.

But this is one of the great things about informational interviews.  You can ask professionals directly about this stuff, to address that information gap and feel less isolated in the job hunt.

Step 1: What do you want to accomplish?

Before you start doing informational interviews, think about what you really want.  I know, the answer is often “I don’t know,” and that’s fine!  But dig down into what you don’t know.  You don’t know how to write a cover letter people actually want to read?  You don’t know what jobs are available in this industry you got a degree in but are struggling to use?  You do know everything currently sucks and you want to make a change, but you don’t know what to do instead?  These are all fair game.  Some examples:

  • “I’m looking to make a career change, and I want to learn more about these jobs that look interesting to me.”
  • “I want to reach a high level position in my career, and I’m hoping to learn more about how to get there.”  
  • “How the hell do hiring people think?  I’m looking for a job in ____ but the job search is going slowly, and I want a better understanding of how to be successful at it.”
  • “I’ve got this weird assortment of skills, and I see people doing this kind of work.  I think I could do it, but I’d like to learn more to find out.”
  • “I want to go to school for ____, but I’d like a better idea of what I want to do with the degree once I get it.”

It’s fine if you have more than one agenda!  But you want to get an idea of where you’re going with this.  There’s no point in wasting your own time and theirs.  Besides, they’re probably going to ask you about this during the interview, because they’ll be hoping they can help more if they understand what you want.

Step 2:  Identifying people to ask for interviews

For anxiety-free interviewing, the best place to start is with people you already know!  When I decided to go back to school, I asked for an interview with the Assistant Dean of Libraries at my old job.  That might sound impressive, but he was my boss’s boss.  He knew my name, I’d talked to him at ice cream socials, he sat down with each of us once a year to get our opinions of the department.  Because I already knew him, I didn’t have to worry so much about being proper or making a good impression.  It was much more relaxed.

So, ask your current colleagues.  Ask friends and members of your various communities who do things you want to know more about.  Ask people you know in fandom, or online.

Also: Ask your co-workers and friends if they know anybody they could introduce you to.  They may be a stranger, but it’s a bit less stressful if you both have someone in common.

Another good source: people you used to be familiar with and want to renew contact with, but you feel awkward about it.  E.g. college professors, old supervisors, etc.  Particularly great if you’re hoping to ask them for a reference or letter of recommendation but you want to be sure they remember who you are first.

A fourth place, if you’re a college grad, is your college’s Career Services or Alumni Office.  Even though you’ve graduated, most colleges continue to make these resources available to their alumni.  After all, if you do well, it reflects well on them.  (PS: they often also help alumni with resume and cover letter advice, and other professional development stuff.)  The great thing about taking this route is that they’re putting you in touch with people who’ve already volunteered to be contacted, so you know you’re not wasting anybody’s time and you’re unlikely to get turned down.

Most stressful for most people, but still worth a shot sometimes, is asking someone you admire from a distance for an informational interview out of the blue.  This can end up making you some pretty cool new contacts.

But wait!  It’s not time to start composing your request yet.  Once you pick out targets, get your questions in order BEFORE you contact them.

Step 3: Lining up your questions

This comes before asking for the interview, because once you contact the person you want to ask for an interview, they may suggest a meet-up with a very quick turnaround time.

Those of us who suffer from anxiety will be glad to hear that it’s best to plan to keep it short.  Assume you’ll probably have about 15-30 minutes of time.  So you want to keep this interview targeted, subject-wise. 

For each person you plan to request an interview from, do your homework on them, and work out the set of questions you want to ask them.  

Most of us have LOTS of questions about jobs, but each person you interview will probably have a thing that it’s most valuable to talk to them about.  For one person, you might focus on, “You started in a similar place to me; how did you get where you are now?”  For another, you might go with, “You’ve been in a hiring position for years; what can you tell me about applying for jobs from the hiring manager’s side?”  Or “You’re an expert in this field; how has it changed since you started, and what are the most valuable skills and experiences for a newbie these days?”  Or “I admire your work so much; can you tell me what works for you in getting all this done?”

I’ve framed each of these subjects here as a single question, but each is really a whole conversation subject.  You can probably see how you could talk to somebody for 20 minutes about each of these, easy, so you’ll want to unpack them and break them out into smaller questions.  

You’ll want to prepare more questions than you expect to have time for, but you want to front-load the ones that are most important to you.  Chances are, in that space of time, you won’t end up asking more than five, but you want to have extras in case you breeze through them.

Once you actually start the interview, you might come up with others or discover that some of the ones you already had planned are irrelevant.  And that’s okay.  

You can poke around online and find lots of articles to help you figure out good questions for an informational interview.  One of the questions should always be, “Do you have anybody else you’d suggest I talk to?”  This accomplishes two things: it lines up more people with good information, and it’s networking!  Yay!  You’ve got a reference! 

Oh, and prep your resume and cover letter.  You’re not out to ask for a job, but it’s good to have a copy of each on hand.

For lots more on this, google “informational interview questions.”

Step 4: The Request

How do you contact them?  I usually go with email.  If you already know them comfortably, then of course you could just walk up and ask, or drop a Twitter DM or Tumblr ask or whatever the local social media equivalent is.

What do you say?  It depends on your relationship with them.  Obviously, for someone who’s a friend or co-worker you can just be all, “Hey, Jess, you do a lot of the hiring for your office, can you help me unveil the mysteries of the fucking job app?  I am about to lose my mind.”

For someone who is being referred to you, then what I do is ask the person putting us in touch to kick things off.  My friend can ask their friend if they’d be willing to talk to me, and if the answer is yes, then my friend can send an introduction email and cc us both on it.  This takes a lot of the initial pressure off.  If you go through a Career or Alumni Office, it’s probably their standard operating procedure.

So, the message.  Since cold contacts are the hardest, here’s an example:

“Hi!  My name is ____.  You don’t know me, but I really admire your work (specific is better; e.g. ”your work on (project x)”).  I’m starting out in a career in _____ myself.  It’s really inspirational to me to see you working at your current level.  Would you be willing to meet up with me over coffee, to help me gain a better understanding of how I can prepare myself to be successful in this field?  I know you must be very busy, so I wouldn’t ask for more than 20 minutes of your time.”

Important elements:

1: “I admire your work on ____” – This line–or something like it–is where you establish that you are paying attention to what they do and that you value it.

2: “I’m starting out in a career in _____ myself.  It’s really inspirational to me to see you working at your current level.“ – A line like this–or similar, like “I’m very interested in working for (Company X) myself.”–lets them understand what motivated you to contact them, and what you’re looking to accomplish.

3: “

Would you be willing to meet up with me over coffee, to help me gain a better understanding of how I can prepare myself to be successful in this field?“ – This is the request.  You don’t need to detail the exact questions you want to ask, but being specific lets them see exactly what you’re looking for from them.  If you’ve got anxiety, you can particularly appreciate how much less looming and amorphous it feels if they can more easily envision the conversation.  (Hey, lots of high-powered professionals have anxiety too!)

4: “over coffee” – Specify what kind of meeting you’re asking for. Face to face?  By email?  If you know the area, you can get more specific.  “The cafe in the lobby” or “the Starbucks down the street.”  Schedule-wise, usually it’s best to leave it “at your convenience.”  Or you could go with “whatever place and time would be most convenient to you.”  Who knows?  Maybe they’ll just ask you to stop by their office for a chat!

If you’ve got anything in common, absolutely play that up.  This helps to both establish a connection and let them get a better understanding of exactly what you’re looking for.  Things like:

  • “I’m a fellow graduate of ____ University.”  (Alumni eat this up with a spoon.  It’s a real ego boost to think of yourself as mentoring the next generation.)
  • “I saw that you studied _____ degree, just like I did.  Could you help me gain some insight on how I can take that into ___(e.g. “a managerial role”; “field research” etc.)?”
  • “I’m a friend of ____, who suggested that you’d be a good person to talk to about a career in ____.”

Sometimes people will ask to talk over coffee or, if you’re feeling ambitious, over lunch.  It can be enticing, especially for a hard-working professional, because it represents a little break in their day, and having food or a beverage can help break the ice a little.  Footing the bill for a treat is also one of the ways in which you can give back to them a bit for their time.  If you take this approach, do expect to foot the bill for them.  They’re doing you a favor.  (Although in some cases they’ve claimed the tab despite my expectation.  This happens most often with professors, I’ve noticed.  They seem to be highly aware of how broke new graduates usually are.)

For those of us who HATE face to face conversations, who don’t have the time or means to get around freely, or who are just too far away from the person we want to talk to, you can also request a conversation by some other medium.  It will be more or less the same as above, except that you say, for example, “Would you be willing to speak to me via email or Skype about…?”

For loads more on this, you can google “informational interview request.”

Step 5: The Reply

Once you’ve contacted them, what can you expect?  Some possibilities:

Sometimes if you request one format–say, face to face–they might come back and say something like, “I don’t have time for that, but we could talk via email.”  So be prepared for that.  Personally I really like email interviews.  I’ll send a message back asking if they’d like to me just send all my questions (in which case I will send them up to five; giant-ass questionnaires are never fun for anybody), or if they’d prefer a slower conversation.  (To date, everyone has asked for the questions; maybe this is just me over-complicating things, but I figure it never hurts to ask if I’m not sure.)

Sometimes they just say sorry, they’re too busy.  This is okay.  

It’s not a rejection.

They probably really are just too busy.  There are plenty of other fish in the sea.

Sometimes they don’t get back to you at all.  In this case, drop them one more polite note maybe 5-7 days later, along the lines of “Hi, this is ___.  I emailed you last week.  I hope you have a few minutes to speak with me, because it would mean a lot to me to get your insights about (thing you previously said).”  Personally, I’d leave it at that.  If they don’t get back to me after the second email, I assume they’re either too busy or honestly don’t want to talk to me, but YMMV.  Some people keep trying.

Step 6: The Interview

Frankly I find this the easiest part.  You’ve got your questions lined up, you’ve laid the groundwork.  This part is just the talking.

They will probably ask you about yourself, and will almost certainly ask you about your current situation and what you’re hoping to learn from them.  So be prepared for that.

They may also ask what motivated you to talk to them, so be prepared for a more detailed response to that, too.

A few things (and I’m probably forgetting some here):

DO NOT ask them if they have a job available, or if they can get you a job, or if they can get you a specific job you’re interested in, or if they’ll take your resume.   In most cases, it’s best to assume that this person you’re talking to is actually unable to personally get you a job, even if they want to.  (This is, in fact, usually the case.)

DO go ahead and ask them what they can tell you about a specific position you’re interested in, if there is one.  Sometimes they can’t tell you much; a lot of companies are big, and one department doesn’t necessarily have a lot to do with another.  It’s fine to let them know you’re interested. Just don’t make it sound like you want them to help you get it.  Think of this as recon.  You’re gathering insider information that can help you when you write your application or land the job interview.  (At this point, sometimes they will voluntarily offer something, such as putting in a good word for you, which is a different story and a great sign.)

DO go ahead and ask them, “What are the best ways to keep an eye out for openings at your company?” or verify, “Is ____ the best method?”  Usually they’ll just point you at the HR site or the jobs database, but sometimes they’ll come up with some other suggestions.

DO bring a resume and cover letter, just in case they ask to see it.  You might even ask if they’d be willing to give you some suggestions for improving it, but don’t ask them to take a copy with them or assume that they’ll take it.  My general approach is to stick it in a folder and carry it like it’s just another set of office documents.  Low key.  (I have had people ask me to send a copy to them before an interview, so that they could review it and give me suggestions for improvement, which was SUPER cool of them.)

Go ahead and fangirl/boy a little–over them, their company, the general awesomeness of their profession, whatever.  It doesn’t hurt anything to show some enthusiasm, and you’re not a robot.  And frankly, “____ is SO COOL because ____” shows you’re legitimately interested and that you have actual reasons for your opinion.

Remember how I said that one of the questions should always be, “Do you have anybody else you’d suggest I talk to?”  Don’t forget to ask this!  If these referrals are strangers, then while you’ve got your interviewee there, ask them if they’d be willing to make introductions.

DO thank them, and offer to help them if there’s ever anything you can do for them.  This shows you have a sense of reciprocity and gratitude.  Chances are there won’t be anything you can help with, but it’s a nice offer.

Step 7: The Follow-Up

Send them a thank you message a day or two afterwards!  They went out of their way for you, and that deserves appreciation.  Also it doesn’t hurt to give them a little reminder. ^_^ (Still do not ask them for a job.)

If you apply for a job at their company or whatever, or if you GET a job, send them another thank you message and let them know.  Again, it does not hurt to remind them, or to show that you’re grateful.

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