‍Questions About The Role / Path

1. Ask yourself "What do I not know about this role that I need to learn more about? What am I unsure about? Where do I need a greater understanding of what this role (or industry) entails?" Reflect first and then list out your authentic questions that will help you get to the point of having a 100% accurate picture and understanding of the role (and/or industry).
2. Ask yourself "What am I concerned about? Do I have any hesitations about this role (or industry) that I can ask about?" (and come up with questions accordingly)
3. "Here's what I know/think this role is… [Define it in your own words]. How do you define/describe the role?" 
4. "If your role was a pie chart, how would you split up the pieces of the pie?" Ask this to get the breakdown of the core functional skill sets and where they spend their time.
   • If they mention any slice of the pie that is over 50%, ask if they can break it down further.
   • Once you hear their answer to the pie chart question, you can do two things, see #5 and #6.
   
5. Compare their answer with your own ideal pie chart. Compare it to what you love doing and where you hope to spend your time. You can always ask a follow up like, "Do you know of a role that does more of [x] and less of [y]?"
6. For any slices of the pie, ask more questions to drill down and understand what those pieces actually entail and how they go about those tasks. This is where you have an opportunity to get them to paint an accurate picture so you can truly imagine what they do and thus what you would do all day in the role.
7. "Here's what I love doing [describe functional areas you particularly love doing]. In your experience, which roles or teams have you seen that perform this type of work or seem most relevant?"
8. "I'm debating [role A, role B, role C]. How do you see the difference between these roles?"
9. "What are some example future paths where people tend to go after this role? Where could this role lead?"
10. "What skills are critical to break into this role?”
11. “What do you look for when hiring candidates for [this role]?”
12. “Do you have examples of the last 2-3 new hires on your team and any patterns of what stood out about these candidates?”
13. “Are there any courses or certifications you think are worthwhile or reputable?" 
14. “Are there any upskilling or learning programs that you or your colleagues have done and liked?”
15. “Given my desire to work on improving X skill, are there resources you suggest I look into?”
16. “Given my desire to work on improving X skill, what do hiring managers most want to see - hands-on experience or certifications/proof of training?”
17. “How have you seen people break into this role or begin on this path?”
18. “Do people in this role typically get hired from another team internally or have there been external hires brought into this role?”
19. “Have you seen mid-stage career professionals pivot into this role/path?” If so, “What did they do particularly well to be able to make a smooth transition into this role/path?”
20. "Are there any other information-based resources you can suggest to me to learn more about this [role/industry] (i.e. blogs, webinars, networking groups, slack groups, etc)?"
21. "Can you walk me through an example/typical project lifecycle?" “What is your role throughout the project lifecycle?
22. “What are some common challenges that someone may typically face in this role?”
23. “What external vendors/partners/stakeholders do you work closely with, outside of your company?”
24. “How does this role vary at a small organization, a medium sized organization, and a large organization?”
25. “How does this role tend to vary at different companies? How do companies approach this role differently?”
26. Consider what else you may want to know or ask about hiring/interviewing/recruiting for this role. You could ask in an open-ended way, “Is there any other tips or guidance you have when thinking about the hiring process for this role?” or You could brainstorm to see if there are specific areas you want to dive into deeper (technical or case interviews, etc).
27. “What should I be asking you? What have I not asked about that I should consider?”
28. “If you had to describe the personality of people who thrive in this role in 3 words, what would you say?”
29. “Given your exposure/experience, what is the typical/standard/market salary range for [this role]?” (Be clear about the level of role, location, size of the organization).

Questions About The Team/Department 

30. "What are the different roles on your team? How do they differ?"
31. "What are the different teams you work closely with? How do they interrelate/interact/differ from one another?"
32. “How is your team structured?”
33. “How is your department structured?”
34. “What challenges is your team/department currently working on overcoming?”
35. “What opportunities is your team/department looking to capitalize on?”
36. Ask questions about the work itself! Prove your knowledge, fit, expertise by reflecting on what they do and what you want to know about their approach, processes, positioning/differentiation, etc.

Questions About The Company

Instead of asking, “what’s the culture like?”, aim to think of the top 3-5 traits you would want to be exhibited in a company’s culture, and then ask things like “Tell me about a time…” or other ways of garnering and soliciting concrete information, examples, and stories. Allow them to show versus tell. Be specific in what you want to ask about the culture. Some examples:

37. “What’s the current company strategy/direction/roadmap?”
38. “What opportunities, initiatives, or programs do you provide for continuous professional development (both hard skills & soft skills)?”
39. “What opportunities, initiatives, or programs do you provide to encourage or set up mentor relationships?”
40. “What are the hours like here? What is the work-life balance like here?”
41. “What are the policies for hybrid or remote work? How have they changed and where do you see them going in the future?”
42. “Tell me about a time that a junior employee shared a new idea or questioned an existing process and how that went.”
43. “What is the performance review/evaluation process like?”
44. “What does the promotion process entail?” “Can you give me a few examples of people on the team who have been promoted and what their journeys were like?”
45. “If you had to describe the personality of the people at this company in 3 words, what would you say?”

Questions About The Industry 

46. “Who are the companies main competitors?”
47. “What market trends are you seeing in the industry?”
48. “How does your organization stand out or differentiate itself?”
49. “Where are things going in the industry, i.e. key innovations? What's the future like? How is your organization planning ahead for it?”
50. Use your knowledge of the industry to see what else comes to your mind to dive into.