Informational interviews are an essential part of the job search process, yet many people are stumped when it comes to how to do them. As a follow up to Secrets of My Success: From Unhappy in NYC to Exciting New Job in San Francisco, I asked LYJ alumna Emily, who successfully obtained her new job through informational interviews, to share how she prepared and what questions she used. Here’s what she reported.

Pre-call: Research the interviewee’s background on LinkedIn. (If you know the interviewee through a friend or referral, ask for as much information as they can give you.) The amount of knowledge you bring to the interview reflects your effort and allows you to ask more specific questions. Below are sample questions you can customize with your research or use as they are:

Informational Interview Questions

Questions to start with:
1. Can you tell me how you got to this position?
2. What do you like most about what you do, and what would you change if you could?
3. What are three things that you enjoy most about working at your company/organization?
4. What are the three most challenging aspects of working at your company/organization?
5. What’s a typical day like for you?
6. How did you get where you are today?

Questions on the company and career field:
1. What’s unique or differentiating about your company?
2. What are the types of jobs that exist where you work and in the industry in general?
3. Where would you suggest a person investigate if the person were particularly skilled at (fill in the blank — quantitative thinking, communications, writing, advocacy)?
4. What does a typical career path look like in your industry?
5. What are some of the biggest challenges facing your company and your industry today?
6. How do you see your industry changing in the next 10 years?

Questions on staying current:
1. Are there any professional or trade associations I should connect with?
2. What do you read — in print and online — to keep up with developments in your field?

Questions on breaking into a career area:
1. How do people break into this field?
2. If you were just getting involved now, where would you put yourself?
3. If I wanted to start in this career area, how would you recommend that I go about pursuing this career path?

To conclude:
1. If you had a chance to do it all over again, what would you have done differently?
2. Is there anything I haven’t asked about that you’d like to tell me?
3. Is there anyone else that you recommend I speak to about this topic/this industry/this career?
4. Would it be all right if I kept in touch with you? How would you prefer that I keep in touch?

For more on this topic, a trusted colleague recommends reading A Foot in the Door by Katherine Hansen and Highly Effective Networking by Orville Pierson.