Question Library
A curated collection of effective questions for every phase of the informational interview process, organized by career stage and conversation goal.
Phase:
Career Stage:
Goal:
Beginning the Conversation
These questions help break the ice and establish rapport in the first 5-10 minutes of your meeting.
Could you tell me about your career journey and how you got to where you are today?
This open-ended question invites the interviewee to share their story in a way that feels comfortable to them, while giving you valuable context about their path.
What does a typical day look like in your role?
This helps you understand the day-to-day reality of their position, which can differ significantly from formal job descriptions.
What attracted you to this industry when you first started, and has that changed over time?
This question works especially well with senior professionals, inviting reflection on their early career motivation compared to their current perspective.
How would you describe the culture at [Company Name]?
This offers insight into the working environment and company values from an insider's perspective.
Middle: Diving Deeper
These questions help you gather specific insights and advice during the main portion of your conversation.
What major changes have you seen in this industry since you started, and where do you see it heading?
This question gives you historical context and future trends from someone with first-hand experience in the field.
What skills or experiences do you think are most valuable for someone looking to advance in this field?
This helps you identify the most important skills to develop for career growth, beyond what might be listed in job descriptions.
What's been the biggest challenge in your career, and how did you overcome it?
This question invites candid reflection and often reveals valuable lessons about resilience and problem-solving.
If you were in my position, what would you focus on or do differently than you did?
This question invites personalized advice based on their own career path and what they've learned along the way.
What do you think are the biggest misconceptions people have about this industry or role?
This question often reveals insider perspectives that can help you avoid common pitfalls or adjust your expectations.
How does your company approach work-life balance and professional development?
This gives you insight into company culture and values around employee wellbeing and growth.
End: The Magic Questions
These critical questions help you transition from a one-time conversation to ongoing opportunities and connections.
Is there an opportunity for someone with my background at your company right now?
This direct question opens the door to potential job opportunities without being too pushy.
Is there anyone else you think I should talk to learn more about this field?
This question helps you expand your network and gain additional perspectives and connections.
What books, resources, or experiences would you recommend for someone looking to develop in this field?
This question helps you gain specific resources for continued learning and development.
Would you mind if I reached out to you in the future with any follow-up questions?
This question opens the door for ongoing communication and relationship building.
Follow-Up Communications
These questions help you maintain connections and continue learning after your initial meeting.
I followed your advice about [specific suggestion] and wanted to share how it's going. Do you have any further thoughts on my approach?
This follow-up shows you valued their advice enough to act on it and creates an opportunity for continued guidance.
I just read this article about [industry trend] and thought of our conversation. Have you seen this development, and what's your take on it?
Sharing relevant content provides value to them while creating a natural reason to reconnect and continue the professional relationship.
I've recently updated my resume based on our conversation. Would you be willing to take a quick look and provide any feedback?
This question creates a specific, bounded request that most professionals can fulfill easily, while keeping you top of mind for potential opportunities.
I'll be attending [industry event/conference]. Will you be there as well? I'd love to reconnect briefly if our schedules align.
This creates a natural opportunity for an in-person follow-up in a professional setting without imposing on their time.