Informational Interview Questions That Help You Decide

The best informational interview questions address something you cannot learn from the person's profile or a basic job description. Ask about actual work, trade-offs, and preparation, then follow the answers rather than racing through a long list. If you have not arranged the conversation yet, start with how to ask for an informational interview and then prepare a focused agenda.

UW-Madison's question guide groups questions around the job, organization, field, and candidate preparation. The original prompts below use those broad areas to help with specific career decisions. Choose a handful that matter to you; this is a menu, not a questionnaire to complete.

If you are deciding whether the work appeals to you

1. What did you work on yesterday, and what was unusual about that day? Asking about an actual day makes it easier to distinguish routine tasks from memorable projects.
2. Which part of a project takes more time than outsiders expect? Follow up on whether that time goes into analysis, coordination, revisions, or something else.
3. What kind of problem do you enjoy solving in this role? Ask for an example without requesting confidential details.
4. What is necessary work here that you do not especially enjoy? Every role has less attractive tasks; you are trying to understand the balance, not expose a complaint.

If you learn that a role is mainly relationship management rather than independent analysis, that can be a useful discovery even if it makes the role less appealing.

If you are exploring how to enter the field

5. When your team last hired someone junior, what helped that person become useful? This is more concrete than asking for the universally best qualification.
6. Which experience from your earlier work transferred well, and which did not? Particularly useful when speaking to a career changer.
7. What could a beginner do to test their interest before committing to an expensive course? Look for a small project, observation opportunity, or public learning resource.
8. What would you investigate about entry routes if you were starting now? Make room for the possibility that the person's own route is no longer typical.

A contact may not know current hiring requirements. Treat suggestions as leads to verify against actual vacancies, not as a guarantee that a certificate or degree is sufficient.

If you need to understand working conditions

9. When does the workload become less predictable, and how is that handled? Ask about the process rather than expecting a promise that every week is calm.
10. Who do you rely on most to finish your work? Follow up on what good collaboration looks like between those roles.
11. What changes when someone moves from a junior to a more experienced position? Responsibilities can matter more than titles.
12. Which parts of your experience are specific to this organization? This directly tests how far you can generalize what you hear.

For an informational conversation, ask about typical compensation structures or public resources if relevant, not the contact's personal earnings. This is different from discussing the compensation of a specific job with its recruiter.

If you have only a few minutes left

Choose one question that turns the conversation into action:

13. What is one assumption in my current plan that I should check? Give a short description of the plan so the question is answerable.
14. Is there a resource or kind of professional perspective I have missed? They can suggest a book or role without having to provide a personal introduction.
15. May I send you a brief update after I explore that suggestion? Ask rather than presuming an ongoing mentoring commitment.

Use the answers without overstating them

Separate a first-person account, an opinion, and something independently verifiable. "Our team trains juniors on this tool" is useful, but it does not mean every employer does.

For an actual hiring conversation, use questions to ask in a job interview instead. If the research helps you choose a new direction, it can inform your career-change explanation, but the conversation itself is not a substitute for building the skills the role requires.