12 Informational Interview Questions to Wow your Contact

Allow me to introduce my absolute favorite job search tool…

Informational Interviewing!

Informational interviewing is a meeting or conversation to learn about the experience of someone working in a field or company that interests you. Informational Interviewing is also the most under utilized and under appreciated job search tool I can think of.

But why?! Here are some of the common objections I hear to informational interviewing:

  • “I don’t want to bother them…”

  • “What if they don’t respond?”

  • “I’m sure they’re really busy…”

  • “But if I’m not asking for a job, why would I waste my time talking to them…”

To which I say:

  • You’re not a bother. You are valuable and provide value to the conversation.

  • Then you’re in the same place you are now and certainly no worse off.

  • Perhaps, but you don’t know unless you ask.

  • Oh, bless your heart. Let’s chat!

Fundamentally, you want your informational interview to show you're thoughtful, that you did your research, and (if possible) you're qualified to work in this field. Here's a link to a blog on more of the foundations for informational interviews. One thing to remember, informational interviews are an art, not a science. You want to show you're prepared and get your questions answered, but it should feel like a conversation, not an interrogation. You won't ask all of these questions - and you may not ask the same questions every time, but this will give you an idea of some questions to ask:

  1. Tell me about your career path. What led you to the role you’re in today?

  2. What is a typical day (or week) like for this role?

  3. What advice would you give someone who is considering this type of job (or field)?

  4. What steps would you recommend someone take to prepare to enter this field?

  5. What skills, abilities, and personal attributes are essential to success in your job/this field?

  6. Do you think there’s a personality type or temperament that’s just not well-suited for this kind of role/field/career?

  7. How did you begin your career? What did some of your early roles look like?

  8. How is success/performance measured in this field?

  9. What are some common career paths in this field?

  10. What do you like most about your work?

  11. What do you like least about your work?

  12. If you could do it all over again, would you choose the same path for yourself? If not, what would you change?

  13. BONUS: Can you suggest anyone else I could contact for additional information about working in the field? If you can get more contacts out of this conversation, that's ALWAYS a win. Just make sure you follow up with the person who made the connection to thank them.

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