There’s nothing worse than asking someone to grant you an informational interview and having nothing to say. This person is sacrificing part of her day for absolutely no ostensible benefit, so you’d better make it a pleasant encounter for her, and more importantly, make her feel like she helped. (It’s a scientific fact that people will feel positively toward you if they feel they’ve done something to help you.) Please, don’t subject them to awkward silences.
Even for a casual informational interview, go in prepared with as much information as you can possibly acquire. Research the company, and even more importantly, give the person’s LinkedIn a thorough review. Find out where she went to college, where she worked before this, her full job history. If you want to ensure that you hit it off, give her a quick stalk on Twitter, find out a few of her interests and see if you can naturally work one into the initial chit-chat portion of the meeting. Making people like you (and thus, want to help you) is not rocket science.
Yes, do your research. Yes, have insightful questions prepared beforehand. Emerge with new information that could help you. But remember that informational interviews are not Q&As. They are “feel me out and see what you think so maybe you’ll like me and be inclined to help in the future” meetings. What I’m saying is: Be friendly. Be casual, but not too casual. Compliment the person without it being obvious. Crack a joke for God’s sake. Approach it almost like you would a first date: Be interested in the other person and make her like you. Now, to business.
1. I know that you [spent ten years at X before this,] but how did you start out in [this industry]?
After the small talk (don’t skip the small talk), make sure they’re aware that you’ve done your research. Phew, they’ll think. I don’t have to waste time explaining my entire career path to this idiot when it’s right there on my very public LinkedIn page. You’re already ahead of the game.
2. Is there something you wish you’d known or a skill you wish you’d had starting out in [this industry]? Or Is there something you wish you had done differently starting out?
This is a question that will almost definitely get you some useful information. Always take advantage of the opportunity to learn from other people’s mistakes.
3. What’s the culture like at [this company] compared to [prior company]?
In all likelihood, this person has worked at one or more comparable companies. Take the opportunity to get a comparison from the best possible source.
4. What’s your biggest challenge in this role?
If this person’s job is one you hope to do one day, this is a great way to get a better sense of what it takes.
5. What do you dislike about this company?
Unlike a hiring manager, random employees will actually give you dirt on a company.
6. Would you mind taking a quick look at my resume?
If this person has any hand in hiring people for this company in any capacity, you want her to take a look at your resume, which you should have on hand at all times. She can point out flaws that you didn’t even know were flaws.
7. How does my experience stack up to others applying for [X level positions]?
Again, this is only if the person has any hand in hiring.
8. What type of personalities fit in best at your company?
I think this is an absolutely crucial question for any informational interview or official job interview, because certain companies have a definite “type.” And you now have the chance to find out if that type is you before you even apply.
9. What is the best way to get my foot in the door here?
Don’t let the conversation end without any tangible next steps. If you want to work at this company, ask what more you can do.
10. Is there anyone else you think I should speak to?
If your informational interviews don’t spark a trail of more people to talk to, you’re doing something wrong. (I can’t pinpoint what exactly because I don’t have all the details on the company, your work experience, or a full-length film of this meeting, but it’s definitely something.) If you hit it off, Judy should say, “You know who should talk to? Ned. Let me give you his email address.” Maybe Judy can’t help you any further, but Ned probably can. And if Ned can’t, then you’d better get Marcia’s email out of him. And so on and so forth until someone offers you an actual interview. If Judy doesn’t spontaneously offer the name of the next person in your trail, you have to ask for it.
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