5 Informational Interview Questions with Substance

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About a year out of college I was meandering the magazine aisle at Barnes & Noble in Seattle when a cover featuring the CEO of a local book publisher caught my eye. I recognized the name from a book my roomies and I loved. It was filled with questions, and we'd choose one to talk about before going on a run (to distract us from the pain...). On a whim, I emailed the CEO and asked if he'd like to have dinner with us. Six weeks later, he replied "yes."  

There's a remarkable vehicle for connecting professionals with recent grads who have big dreams, lots of motivation, and a desire to sit humbly and learn from someone else's journey: It's called an informational interview. 

(If you've never heard of an informational interview, this blog post is not for you...yet. First, sign up for the mailing list, then read the free Career Experiment you'll be able to download called "Talk to an Expert.")

If you have heard of informational interviews, you know this is one of the quickest ways to gather lots of great insights about a career path or industry. But, questions like “What are the best and worst parts of your job?” and “How can I stand out as a great candidate in this field?” only scratch the surface.

When you’re lucky enough to be speaking to a seasoned professional with experience, connections, and deep knowledge of their field, why not take advantage of it?

Sure, some friendly chit chat helps everyone settle in. But once that formality is taken care of, these questions will help you move from a high-level conversation to something with substance - so you leave with not just good information, but insider’s information too.

  1. What are some of the hot topics being discussed in your organization right now, or in your field? What’s at stake on both sides of the discussion?

  2. How would I recognize a great opportunity in this field? What danger signs would suggest that an organization is struggling, or that I should avoid the opportunity?

  3. What organizations in this field should I be keeping an eye on? Who’s driving change, shaking up business as usual, or standing out to you for any reason?

  4. Where does the tribe for this field hang out? Are there any specialized networking groups, online communities, professional associations, or other hubs that I should be connected to?

  5. To my understanding, ___(fill in the blank with an assumption you’re making about the field or have heard to be true, like “only candidates with master’s degrees are taken seriously, even for entry level roles.”)____. From your experience, would you agree? Why or why not?

A few days before your informational interview, send the professional you’ll be meeting a few of your questions along with a confirmation of the meeting time and location. This will give them a bit of time to think about their answers, since they just might need it!