1. What are your main responsibilities in your role?
  2. What is a typical day (or week) like for you?
  3. What kinds of challenges/problems do you encounter in this role?
  4. What kinds of decisions do you make?
  5. What are some big projects you’re working on now or that you’ve finished up in the last few months?
  6. What current issues and trends in the field should I be aware of?
  7. What skills, abilities, and personal attributes are essential to success in your job/this field?
  8. What are the most effective strategies for seeking a position in this field?
  9. What do you wish you knew 5 years ago?
  10. Are there companies or organizations that should be on my radar?
  11. Are there events (conferences, job fairs, meetups, hackathons, etc.) that would be good for me to attend?
  12. Would you be open to looking at one of my projects and giving me some feedback?
  13. Do you have any tips for how to approach the job search?
  14. Do you know of any good opportunities for pro bono work or internships?
  15. Who else would be good for me to talk to?
  16. What practice/informational resources (websites, books, software, etc.) do you recommend?
  17. How do you evaluate candidates when recruiting/interviewing?
  18. What’s something that might surprise people about your role?
  19. What’s missing on your team, or what’s something that could be done better?