An informational interview is a handy tool for job seekers, particularly those who are looking to break into a new industry or get a job at a specific company. These interviews are conducted at the job seeker's request and should be with someone who has experience or connections to the place you want to go in your career. Arguably, the most important thing to remember about an informational interview is that the person you're talking to may not be able to do much for you.
You may go in with high hopes that this chat will end up with a solid job lead or even an outright offer, but that's highly unlikely. Set your expectations lower, and focus on the long-term utility of learning more about the company, job, or industry you're interested in. With that in mind, your questions should be more general and should focus on helping you make the right choices in your job search rather than ending it right there and then.
How Did You End Up Here?
This is a general question, but it will help you understand the steps necessary to get where you're trying to go. And to clarify, by "here," we're not talking about the interview itself. We're talking about the specific job or company you're interested in. As a follow-up to this question, you can ask whether the path described is typical and, if not, what would be a typical way in.
What Is Currently Missing From My Resume/Portfolio?
Ideally, you'll be able to give the person you're talking to some information about yourself, including a current resume and your portfolio. The interviewee might not have time to peruse both in detail, but hopefully they'll at least take a glance. Just in case, you can bring a paper copy of your resume with you for the interviewee to glance over. He or she can then tell you what's missing so you can address those issues ASAP. You might need to take a specific course in something likeGoogle AdWords or just add a few more pieces to your portfolio.
What Personality Traits Are Important for This Job/Field/Company?
Company culture is often a big deal in the tech world, and even if your resume is perfect and your portfolio outstanding, you could find yourself getting rejected from jobs due to "culture fit." That's not to say that you'll need to completely change your personality, but if you think you want to work at a company staffed but hard-charging jock types and you're more of a stay-at-home-and-knit kind of person, you might actually find that a different organization would be a better place to work. Plus, knowing that you already have certain useful personality traits can clue you in on what to lean into as you brand yourself for the job application process.
What Else Do I Need to Know?
Ideally, your informational interview will flow more like a conversation than an awkward interview. That way you can talk more about yourself and your experience with transparent honesty, which can give the interviewee some insight into what you might be mistaken about. Asking an open question like this gives the interviewee the opportunity to be honest about what they're seeing when they talk to you. If you're told you don't have enough experience in a specific area, consider taking a Udacity Nanodegree program to fill in those gaps before you start your job search.