Congrats! You’ve connected with someone new or re-connected with someone who you think could offer some advice along your career path. The phone, video, or in-person meeting is scheduled. Now, what? What will you talk about? How do you ask for advice? What will they be willing to share?

I “Rebeccammend” a 15-25 minute conversation that covers about 3-5 topics or questions so choose those you think will be most insightful and help you get to know your interviewee better in a short window. If you have extra time, throw in a bonus. This allows time to discuss one question in more detail if it sparks interesting conversation, and doesn’t overwhelm the person who has taken the time to share a bit of wisdom. Make sure to share why you reached out to them specifically and where you are in your career so they can tailor the conversation to be relevant to you both.

Here are 31 informational interview questions bound to bring about new ideas to propel you forward, and maybe even give them some topics to keep thinking about well past this one conversation. Have other helpful questions you’ve asked or been asked? Leave them in the comments for us all to learn from!

Current Role/Career

1. Can you describe your current role and how did you find it?
2. How does a typical day in this role go?
3. What do you like most about your company?
4. What’s the company culture like where you work?
5. What’s a current challenge you’re facing at work and what steps are you taking to overcome it?
6. What’s the most recent project you worked on and what impact is it making?
7. Describe a time where you asked for something at work and didn’t receive it?
8. Describe a time where you asked for something at work and did receive it?
9. Can you tell me about a time when you worked on a project and it didn’t turn out as expected? What was the outcome or lesson learned?
10. Can you think of a time when you were surprised in your career?
11. What advice do you have for someone looking to switch roles, industries, or careers?
12. What is(are) your current career goal(s)?
13. How do you define success?
14. What strategies do you use to drive your career growth?

Education

15. How does your education play into your current career?
16. What publications or media are you most interested in currently?
17. How do you stay up to date with industry news?
18. What education opportunities, workshops, or courses would you recommend to learn more about this industry or skill?

Mentorship

19.  How do you go about finding mentors to guide you along your career?
20. Who is one mentor who’s made an impact on you and how?
21.  What advice you’ve been given that guides your career?

Personal

22. How do you work towards work/life balance?
23. What activities are you involved in outside of work?
24. How do you keep up with multiple interests and position them when creating your personal brand?
25. Do you tend to focus on one area of expertise, or a varied set of skills and interests?
26. What do you look forward to most in your personal or professional life?

Interviewing

27. What’s the toughest interview question you’ve ever been asked?
28. Do you have any suggestions on how to respectfully negotiate a salary?

Expanding Your Network

29. Which industry or professional organizations or events do you recommend to get more connected in my career?
30. Based on my background and interests, is there anyone you recommend I have to meet and why? (Don’t forget to ask for an introduction.)
31. What’s the best way for us to stay connected?