Introduction
You’ve landed a coffee chat with someone whose career path you admire. Your heart’s racing. You have 30 minutes to make an impression and gather insights that could shape your future. But here’s the thing: most people blow this opportunity by asking generic Informational Interviews Questions
Informational interviews are goldmines for career advancement. They’re not about asking for a job. They’re about building relationships, understanding industries, and uncovering opportunities you didn’t know existed. The right informational interview questions can transform a casual conversation into a career-defining moment.
In this guide, you’ll discover the exact questions to ask during informational interviews. You’ll learn how to structure your conversation, what to avoid, and how to follow up in ways that keep doors open. Whether you’re exploring a new field, pivoting careers, or simply expanding your network, these strategies will help you maximize every conversation.
What Makes Informational Interview Questions Effective
Not all questions are created equal. The best informational interview questions do three things simultaneously: they show you’ve done your homework, they invite detailed responses, and they create natural conversation flow.
Generic questions like “What do you do?” waste precious time. Your contact already knows you researched them. Instead, you want questions that spark genuine enthusiasm. People love sharing their journey when someone asks thoughtfully.
Effective questions are open-ended. They start with “how,” “what,” or “can you describe.” These prompts encourage storytelling rather than yes-or-no answers. When someone tells you a story, you learn context, emotion, and nuance that surface-level facts can’t capture.
Timing matters too. Early questions should build rapport. Mid-conversation questions dive deeper into specifics. Final questions should focus on actionable next steps and connections. This progression feels natural and respects your contact’s time.
Essential Questions About Their Career Journey
Understanding someone’s career path reveals patterns you can apply to your own. These questions uncover the decisions, pivots, and lessons that shaped their trajectory.
Start with their origin story:
- “What drew you to this field initially?”
- “Can you walk me through how you transitioned from [previous role] to [current role]?”
- “What was the most surprising turn your career took?”
These questions reveal motivations and adaptability. You’ll hear about unexpected opportunities, calculated risks, and moments of clarity. Pay attention to how they describe challenges—this shows you what obstacles to anticipate.
Dig into decision-making:
- “What factors did you consider when making that career move?”
- “Looking back, which decision had the biggest impact on where you are today?”
- “Have you ever regretted a career choice? What did you learn from it?”
Everyone makes mistakes. Successful people learn from them. When someone shares what they’d do differently, you’re getting battle-tested wisdom without the battle scars.
Explore their current role:
- “What does a typical day look like for you?”
- “What aspects of your job energize you most?”
- “What parts of your role were different from what you expected?”
Daily realities often clash with job descriptions. Understanding the gap between expectation and reality helps you make informed decisions about pursuing similar paths.
Questions That Uncover Industry Insights
Industry knowledge separates informed candidates from hopeful amateurs. These informational interview questions reveal trends, challenges, and opportunities within a field.
Ask about the current landscape:
- “How has this industry changed since you started?”
- “What trends are you watching closely right now?”
- “What challenges is your industry facing that outsiders might not see?”
Industries evolve constantly. Someone who’s been in the field for years spots patterns newcomers miss. This perspective helps you understand where opportunities are growing and where they’re shrinking.
Understand required skills:
- “What skills have become more important in your field recently?”
- “What capabilities do you wish you’d developed earlier in your career?”
- “Are there any certifications or qualifications that make a real difference?”
Job postings list requirements, but insiders know which skills actually matter. Some listed requirements are nice-to-haves. Others are non-negotiables. This distinction is critical for targeting your learning efforts.
Explore company culture:
- “How would you describe the culture at your organization?”
- “What type of person tends to thrive in your company?”
- “What surprised you about working here compared to other places?”
Culture determines happiness and success. A perfect job at the wrong company becomes miserable. These questions help you understand if you’d fit before you ever apply.
Questions About Challenges and Problem-Solving
Every role has frustrations. Understanding them prevents unpleasant surprises and shows you’re thinking realistically about the work.
Address difficulties directly:
- “What’s the most challenging aspect of your job?”
- “How do you handle [specific challenge relevant to the role]?”
- “What keeps you up at night professionally?”
People appreciate honesty about difficulties. It shows maturity. When someone describes challenges, listen for whether they energize or drain them. The same problem might excite one person and exhaust another.
Learn coping strategies:
- “How do you maintain work-life balance in this field?”
- “What strategies help you manage stress in your role?”
- “Have you experienced burnout? How did you address it?”
Mental health and sustainability matter. Ambitious people often ignore these questions until burnout hits. Learning prevention strategies early protects your long-term career health.
Understand failure:
- “Can you share a project that didn’t go as planned? What happened?”
- “How does your organization handle mistakes?”
- “What’s considered a career-limiting mistake in your field versus a learning opportunity?”
Failure is inevitable. Companies and industries handle it differently. Some treat mistakes as learning opportunities. Others punish them harshly. Knowing this helps you assess risk tolerance and cultural fit.
Questions That Build Your Network
Informational interviews should extend your network beyond your immediate contact. The best conversations end with new connections and resources.
Ask for recommendations:
- “Who else should I talk to as I explore this field?”
- “Are there any industry events or communities you’d recommend?”
- “What resources—books, podcasts, newsletters—have shaped your thinking?”
Most people enjoy connecting others. When someone refers you to their network, they’re vouching for you. This implied endorsement opens doors. Always follow up and let your original contact know how the connection went.
Explore professional development:
- “What professional organizations do you find most valuable?”
- “How do you stay current with industry developments?”
- “Are there any online communities or forums you’d recommend?”
Professional growth continues throughout your career. People who advance intentionally invest in learning. These questions reveal where insiders go for information and connection.
Understand advancement paths:
- “What does career progression typically look like in this field?”
- “How do people usually move up or pivot within your industry?”
- “What differentiates someone who advances quickly from someone who plateaus?”
Career ladders aren’t always clear. Some industries value specialization. Others reward generalists. Understanding advancement patterns helps you make strategic decisions about skill development and positioning.
Questions About Breaking Into the Field
If you’re exploring a career change or entering a new industry, these informational interview questions address your specific situation.
Address your transition:
- “What advice would you give someone trying to break into this field?”
- “How important is [specific background/degree] for entering this industry?”
- “What transferable skills from other fields are most valuable here?”
People love helping career changers who show genuine interest. Be specific about your background. The more context you provide, the more tailored their advice becomes.
Understand entry points:
- “What roles do people typically start in?”
- “Are there alternative pathways into this career besides [traditional route]?”
- “How did people on your team get started?”
Multiple paths lead to most destinations. Traditional routes aren’t always necessary or optimal. Sometimes lateral moves or unconventional backgrounds provide advantages.
Learn about obstacles:
- “What challenges do career changers face that I should prepare for?”
- “How can I make my application stand out as someone coming from [your background]?”
- “What misconceptions do outsiders have about breaking into this field?”
Forewarned is forearmed. Understanding barriers helps you develop strategies to overcome them. Some obstacles are significant. Others are perceived barriers that insiders know aren’t real.
Questions to Avoid During Informational Interviews
Certain questions undermine your credibility or make contacts uncomfortable. Avoid these pitfalls.
Never ask about open positions directly. This transforms an informational interview into a job interview. If your contact wants to discuss opportunities, they’ll bring it up. Your job is to impress them so much that they want to help you.
Don’t ask questions easily answered by Google. Asking “What does your company do?” signals laziness. Do basic research beforehand. Use your time together for insights you can’t find online.
Avoid overly personal questions early. Salary questions make sense eventually, but lead with professional curiosity. Build rapport first. Once someone trusts you, they’re more likely to share sensitive information.
Skip questions with yes-or-no answers. “Do you like your job?” is a dead end. “What do you love most about your job, and what would you change if you could?” invites conversation.
Don’t dominate the conversation. This is an interview, not a monologue. If you’re talking more than 30% of the time, you’re talking too much. Your goal is to learn, not to impress with your knowledge.
How to Structure Your Informational Interview
A successful informational interview follows a natural flow. Here’s how to structure your conversation for maximum impact.
Opening (5 minutes): Express genuine gratitude. Briefly explain why you requested this meeting. Confirm how much time they have available. This shows respect and professionalism.
Background (5-10 minutes): Ask about their career journey. Let them tell their story. Listen for themes, decision points, and lessons. This builds rapport and provides context for deeper questions.
Deep dive (15-20 minutes): Explore specific topics based on your goals. Ask about industry insights, daily responsibilities, challenges, and opportunities. This is where you uncover valuable information.
Networking and next steps (5 minutes): Request recommendations for other contacts, resources, or communities. Ask if you can follow up with additional questions. Clarify how you can be helpful to them.
Closing (2-3 minutes): Thank them sincerely. Confirm any next steps. Ask permission to stay in touch. End on time or early—never run over.
This structure feels conversational while ensuring you cover essential topics. Adapt based on how the conversation flows naturally.
Following Up After the Informational Interview
The follow-up is as important as the interview itself. This is where casual contacts become lasting relationships.
Send a thank-you note within 24 hours. Reference specific insights they shared. Explain how their advice will influence your decisions. Be specific—generic thank-yous are forgettable.
Update them on your progress. If they suggested resources or contacts, let them know you followed through. People want to see their advice made a difference. This encourages continued investment in your success.
Provide value when possible. Found an article they’d find interesting? Send it. Have a connection that could help them? Make an introduction. Relationships are reciprocal. Even as the “junior” party, you can contribute.
Stay in touch periodically. Check in every few months with meaningful updates. Don’t contact only when you need something. Build genuine relationships, not transactional ones.
Acknowledge milestones. If their advice led to an interview, job offer, or important decision, tell them. People love knowing they made a difference. This recognition strengthens your relationship.
Preparing Questions Based on Your Goals
Tailor your informational interview questions to your specific objectives. A person exploring career options asks different questions than someone targeting a specific company.
For career exploration: Focus on industry overviews, day-to-day realities, and comparison between related fields. You’re gathering breadth rather than depth. Cast a wide net to understand options.
For career transition: Emphasize transferable skills, entry strategies, and challenges career changers face. You need practical advice for bridging from where you are to where you want to be.
For industry research: Dig into trends, competitive landscape, and future outlook. You’re developing expertise in the field itself, not just a specific role.
For company-specific insights: Explore culture, values, interview processes, and what makes people successful there. You’re assessing fit and preparing for potential applications.
For skill development: Ask what capabilities matter most, how they developed expertise, and what resources accelerated their learning. You’re creating a development roadmap.
Your questions should reflect your stage and goals. Generic questions produce generic insights. Specific, thoughtful questions yield actionable intelligence.
Common Mistakes to Avoid
Even well-intentioned people make errors that diminish informational interview effectiveness. Avoid these common pitfalls.
Being unprepared. If you haven’t researched your contact or their organization, it shows. Preparation demonstrates respect and seriousness. It also enables more sophisticated questions.
Treating it like a job interview. You’re gathering information, not pitching yourself. Stay curious, not desperate. The harder you push for opportunities, the less likely people are to help.
Asking for too much time. Request 20-30 minutes maximum. People are busy. If the conversation flows well, they’ll extend it. Always end on time unless they explicitly suggest continuing.
Failing to follow up. Most people never send proper thank-you notes. This simple step sets you apart. It also keeps the relationship alive for future interactions.
Taking without giving. Relationships require reciprocity. Always ask how you can be helpful. Even if they insist they need nothing, the offer itself matters. Look for opportunities to provide value over time.
Recording without permission. Some people want to record for notes. Always ask first. Many people speak more freely when not being recorded. Respect their preference.
Conclusion
Informational interviews are relationship-building tools disguised as research conversations. The questions you ask reveal your thinking, professionalism, and potential. They also unlock insights no website or article can provide.
Great informational interview questions are thoughtful, specific, and focused on learning rather than asking. They show respect for someone’s time while diving deep into topics that matter. They open doors to opportunities you didn’t know existed and relationships that shape your career trajectory.
Start small. Reach out to one person this week. Prepare thoughtful questions. Have a genuine conversation. The career insights and connections you gain will surprise you. Each conversation builds confidence, clarity, and network strength.
Who in your network could you learn from today? What’s stopping you from reaching out?
FAQs
How many questions should I prepare for an informational interview?
Prepare 8-12 questions but don’t feel obligated to ask them all. Conversations should flow naturally. Some questions may be answered without directly asking. Others might spark new directions you hadn’t planned. Quality matters more than quantity. Focus on questions that genuinely interest you and can’t be answered through basic research.
How long should an informational interview last?
Request 20-30 minutes and stick to that timeframe. Busy professionals appreciate brevity. If the conversation is going well, they’ll extend it. Ending on time or slightly early shows respect. It also leaves them wanting more, which improves the chances they’ll agree to future conversations or introductions.
Is it appropriate to ask about salary during informational interviews?
Approach salary questions carefully. Early in the conversation, focus on role responsibilities and career paths. Once rapport is established, you can ask about salary ranges for specific roles or how compensation typically progresses. Frame it as gathering information for planning rather than negotiating. Most people will share general ranges if asked professionally.
Should I bring a resume to an informational interview?
Only if specifically requested. Bringing an unsolicited resume makes the meeting feel like a job interview, which isn’t the purpose. However, you can offer to send your resume after the conversation if they express interest in your background or mention knowing of potential opportunities. Let them request it rather than pushing it on them.
How do I find people for informational interviews?
Start with your existing network—friends, family, colleagues, and alumni from your school. Use LinkedIn to identify people in roles or companies you’re interested in. Professional associations and industry events also provide connections. When reaching out cold, personalize your message and explain specifically why you’re interested in speaking with them.
What if someone says no to my informational interview request?
Don’t take it personally. People are busy and may not have time. Thank them for considering your request and ask if they could recommend someone else to speak with. Some people who decline initially may agree to connect later. Leave the door open politely and move on to other contacts.
Can I ask the same person for multiple informational interviews?
Yes, but space them out and show progress between conversations. If someone was helpful initially, you can reach out months later with an update and new questions based on your development. Make each conversation valuable by doing your homework and asking evolved questions that reflect your growth.
How formal should I be during an informational interview?
Match your contact’s tone. Start professional but be prepared to relax if they do. Most informational interviews are conversational rather than formal. Being personable and genuine matters more than rigid formality. That said, maintain professionalism—this isn’t a casual chat with friends.
What’s the best way to take notes during an informational interview?
Ask permission first, then take brief notes on key insights. Don’t transcribe everything—this breaks eye contact and disrupts flow. Jot down main points, names, or resources mentioned. Immediately after the interview, expand your notes while everything is fresh. This captures both facts and impressions.
Should I connect on LinkedIn before or after the informational interview?
Send your connection request after the interview, along with your thank-you note. Reference your conversation in the connection message. This timing feels more natural and less pushy. If you’re connected before the interview, review their profile again for recent updates or shared connections to reference during your conversation.
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