How to prepare for your informational interview

If you’re not sure what an informational interview even is, it’s basically a chill conversation with someone over coffee, and the objective is to learn some stuff that will help you navigate your career.

You can learn more about why you should have informational interviews and how to ask for one here. But once you’ve got that covered you need to prepare your questions. So let’s dive in…

Start by making a mental list of the stuff you want to know, the things that would help you make some decisions as you navigate your career. If you had a knowledgeable, benevolent unicorn of a human being sitting across from you over a cup of coffee, what questions would you ask?

You might include general questions like:

• What is your typical day like?
• What do you like/dislike about your job?
• How did you come to work in this field?

You should probably include lots of specific questions about the things that matter to you. For example, if I were doing an informational interview, here are some questions I’d ask because they’re directly related to the stuff I personally care about and would need to know to make a good career decision:

• How closely do you work with your colleagues/clients?
• How much autonomy do you have in your work?
• What kind of problems do you help people with?
• Do you work on projects for a long stretch of time or switch tasks frequently?
• Are research or statistics a big part of your job?
• Do you get to teach or mentor much in your work?

And the list goes on.

Also ask:

• Is there anything else you think I should know (Just in case there's something important I've overlooked.)
• Is there anyone else you think I should talk to? (Because that might get me some great leads for more people to talk to.)

Then I’d thank them for their time and then go home and scribble notes like a mofo so I wouldn’t forget anything.

By the way, this isn’t some bullshit hypothetical “best practices” thing I’m asking you to do but would never do myself. I’ve done this. Lots of times. I still do this years into my career. Before I went to grad school, I reached out to a bunch of professors and students in a bunch of graduate programs. I asked them what it was like, what to expect, what they liked about it, what they didn’t, what the workload was like, everything I could think of.

When I wanted to write for big publications like Forbes and Inc. and Entrepreneur (with no portfolio and no idea what the hell I was doing), I reached out to journalists and contributors to figure that shit out. I asked embarrassingly basic questions like, So what is a pitch, exactly? Who do you send it to? Should I do this over email? Keep it short, or longer with elaboration? Include writing samples? Let’s not forget I had a journalism degree. I should have known this stuff, but I didn’t. So I had to ask.

Before I wrote my first book, I reached out to other authors — all of them total strangers. How else was I gonna do it? Who the hell just knows how to write a book? I didn’t. In every case — with grad school, getting published, writing a book, making a career change — I did as much research as I could on my own and then reached out to a bunch of strangers I thought could help. Many of them said no or didn’t even get back to me (rejection is a part of it — don’t take it personally), some of them said yes, some of them were helpful, and some of them were not. And it was worth it. EVERY. TIME.

If you haven’t already, it’s time you tried informational interviews too. Good luck!