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Informational Interviews: How to Learn, Network, and Land Opportunities


You want to break into a new field. You want advice from someone who’s done it. But you don’t know them personally.

Solution: The informational interview.

What it is: A 20-30 minute conversation where you ask someone about their career, industry, or role—NOT a job interview.

Why it works:

  • People love talking about themselves (90%+ say yes to genuine requests)
  • You learn insider knowledge you can’t Google
  • You build relationships that lead to opportunities
  • You get advice tailored to YOUR situation

The hidden benefit: 50-70% of jobs are never posted publicly. Informational interviews give you access to this hidden job market.

This guide will show you:

  • How to request an informational interview (templates included)
  • What questions to ask (15+ proven questions)
  • How to turn conversations into job offers
  • Common mistakes that kill opportunities

What Is an Informational Interview?

Definition: A casual conversation where you learn about someone’s career path, industry, or company.

What it’s NOT:

  • ❌ A job interview (you’re not asking for a job)
  • ❌ A sales pitch (you’re not selling anything)
  • ❌ A favor (you’re giving them a chance to help and feel good)

What it IS:

  • ✅ Research (learning about a field or role)
  • ✅ Networking (building a relationship)
  • ✅ Positioning (showing you’re serious and prepared)

Example scenario:

  • You’re a customer support rep who wants to transition to sales
  • You find 5 people on LinkedIn who made that transition
  • You request 20-minute informational interviews
  • You learn what skills to build, how they made the switch, and who’s hiring
  • One person introduces you to their hiring manager
  • You get an interview (that wasn’t posted publicly)

Success rate: This works 60-80% of the time when done right.

Why People Say Yes (Even to Strangers)

Reason 1: Reciprocity

  • Someone helped them when they were starting out
  • They want to pay it forward

Reason 2: Ego/Validation

  • Being asked for advice feels good
  • It positions them as an expert

Reason 3: Building Their Network

  • You might be useful to them someday
  • Smart people invest in relationships early

Reason 4: Low Commitment

  • 20 minutes is easy to say yes to
  • No obligation beyond the conversation

Key insight: You’re not asking for a favor. You’re offering them a chance to help someone and feel good about it.

Who to Ask for Informational Interviews

Tier 1: Warm Connections (Highest Response Rate)

People you have a connection to:

  • Alumni from your high school (even without college, this works)
  • Friends of friends (ask for an introduction)
  • Former coworkers or managers
  • People in online communities you’re active in

Response rate: 70-90%

Tier 2: Weak Connections (Medium Response Rate)

People you’ve interacted with but don’t know well:

  • LinkedIn connections you’ve commented on their posts
  • People who attended the same conference/meetup
  • Members of the same professional groups

Response rate: 40-60%

Tier 3: Cold Outreach (Lower Response Rate)

Complete strangers:

  • People at your target companies
  • Industry leaders you admire
  • Authors of articles you found helpful

Response rate: 15-30% (but still worth it)

Pro tip: Start with Tier 1 and 2. Build confidence. Then try Tier 3.

Who to Avoid (Red Flags)

Don’t reach out to:

  • ❌ CEOs of Fortune 500 companies (too busy, won’t respond)
  • ❌ Influencers with 100K+ followers (flooded with requests)
  • ❌ People in totally unrelated fields (unless transitioning)

Do reach out to:

  • ✅ Mid-level professionals (5-10 years ahead of you)
  • ✅ People who post about helping others
  • ✅ Those who explicitly say “happy to help”

How to Request an Informational Interview

The Formula

Subject line: Specific + Brief Opening: Personalized compliment or connection The ask: Clear, low-commitment The why: What you want to learn The close: Make it easy to say yes

Template 1: Warm Introduction (Friend of Friend)

Subject: Quick question about [their role] (referred by [mutual friend])

Hi [Name],

[Mutual Friend] suggested I reach out to you. I'm exploring a transition from [your current role] to [target role] and [Mutual Friend] mentioned you made a similar move a few years ago.

Would you be open to a 20-minute call where I could ask a few questions about your experience? I'd love to hear how you made the transition and what you learned along the way.

I'm flexible on timing—happy to work around your schedule.

Thanks for considering!

[Your Name]

Why it works:

  • Mutual connection (immediate credibility)
  • Specific ask (20 minutes, not vague)
  • Clear purpose (transition advice)
  • Low pressure (easy to say yes)

Template 2: Weak Connection (LinkedIn)

Subject: Learning from your [specific thing]

Hi [Name],

I've been following your posts on LinkedIn about [specific topic—e.g., product management] and found your recent post on [specific post] really helpful.

I'm currently working as a [your role] and exploring a move into [target field]. I'd love to learn from your experience—specifically how you got started and what skills made the biggest difference.

Would you be open to a brief 20-minute call? I'm happy to work around your schedule.

Thanks for considering!

[Your Name]

Why it works:

  • Shows you’ve done research (specific post reference)
  • Flattery (people love hearing their content is helpful)
  • Clear, specific ask
  • Respects their time (20 minutes)

Template 3: Cold Outreach (No Connection)

Subject: Quick question about your career path

Hi [Name],

I came across your profile while researching [industry/company] and was impressed by your transition from [previous role] to [current role].

I'm a [your current role] exploring a similar move and would love to learn from your experience. Specifically, I'm curious about [1-2 specific questions—e.g., "what skills you prioritized" or "how you positioned yourself for the transition"].

Would you be open to a brief 15-20 minute call? I know you're busy, so I'm happy to keep it focused and respect your time.

Thanks for considering!

[Your Name]

Why it works:

  • Specific (you researched their background)
  • Focused (clear what you want to know)
  • Short (15-20 minutes)
  • Acknowledges their time is valuable

Follow-Up (If No Response)

Wait 5-7 days, then send a polite follow-up:

Hi [Name],

I know you're busy, so I wanted to follow up on my message from last week.

I'm still hoping to learn from your experience transitioning from [X] to [Y]. Would you have 15-20 minutes for a quick call?

Totally understand if the timing doesn't work—either way, thanks for considering!

[Your Name]

Rule: Follow up ONCE. If no response, move on.

What Questions to Ask (The Good, The Bad, The Ugly)

Questions NOT to Ask

❌ “Can you get me a job?”

  • Too direct, kills the relationship

❌ “What’s your company hiring for?”

  • Sounds like you’re using them

❌ “What do you do all day?”

  • Too vague, shows you didn’t research

❌ “Can I send you my resume?”

  • Not the purpose of informational interviews

Questions TO Ask (By Category)

Category 1: Their Journey

1. “How did you get into [their field]?”

  • Reveals their path (often nonlinear)
  • Shows what skills/experiences mattered

2. “What surprised you most about the transition?”

  • Uncovers hidden challenges
  • Gives you realistic expectations

3. “If you were starting over today, what would you do differently?”

  • Reveals shortcuts and mistakes to avoid
  • Extremely valuable

4. “What do you wish you’d known before making the switch?”

  • Another way to ask about mistakes
  • Often yields gold

Category 2: Skills and Preparation

5. “What skills have been most valuable in your role?”

  • Prioritizes what to learn
  • May be different than job descriptions say

6. “How did you build [specific skill] without formal training?”

  • Tactical advice (courses, books, projects)
  • Especially valuable if they’re also self-taught

7. “Are there any certifications or courses you’d recommend?”

  • Specific resources
  • Signal of credibility

8. “What’s one skill most people overlook but is critical?”

  • Hidden gems
  • Differentiates you

Category 3: Industry Insights

9. “How is [industry] changing, and what should I be aware of?”

  • Shows you’re thinking long-term
  • Reveals trends

10. “What are the biggest challenges facing [industry] right now?”

  • Demonstrates curiosity
  • Helps you speak intelligently in interviews

11. “Who are the best people to follow or learn from in this space?”

  • Expands your network
  • Points you to more resources

Category 4: Job Search Strategy

12. “How did you find your current role?”

  • Reveals hidden channels (referral, networking, recruiter)
  • May not be through job boards

13. “What makes a strong candidate stand out in [field]?”

  • Shows what hiring managers value
  • Helps you position yourself

14. “Are there any companies or teams you’d recommend I look into?”

  • Specific leads
  • May lead to introductions

15. “Is there anyone else you’d recommend I talk to?”

  • MOST IMPORTANT QUESTION
  • Expands your network
  • Often leads to more informational interviews

Category 5: Wrap-Up

16. “What’s the best way to stay in touch?”

  • Keeps relationship alive
  • Shows you’re not just using them

17. “Is there anything I can help you with or share that might be useful?”

  • Reciprocity
  • Positions you as valuable (not just taking)

The Ideal Interview Flow (20-30 Minutes)

Minutes 0-5: Build rapport

  • Thank them for their time
  • Small talk (recent project, company news)
  • Briefly share your background (30 seconds)

Minutes 5-20: Ask prepared questions

  • Start with their journey questions
  • Move to skills and industry insights
  • End with job search strategy questions

Minutes 20-25: Wrap up

  • Ask for introductions (“Anyone else I should talk to?”)
  • Ask how to stay in touch
  • Offer to help them

Minutes 25-30: Thank and follow up logistics

  • Thank them again
  • Confirm next steps (if any)
  • Promise to follow up with update

How to Conduct the Interview (Phone, Video, In-Person)

Phone Interview (Most Common)

Pros:

  • Easy to schedule
  • No need to dress up
  • Can take notes easily

Cons:

  • Harder to build rapport
  • Can’t see body language

Tips:

  • Find a quiet space
  • Have questions written out
  • Take notes (tell them you’re taking notes)
  • Smile (it comes through in your voice)

Video Interview (Zoom, Google Meet)

Pros:

  • Face-to-face builds better connection
  • See body language
  • Still convenient (no travel)

Cons:

  • Technical issues possible
  • Need good lighting/setup

Tips:

  • Test technology 10 minutes before
  • Professional background (or blur)
  • Look at camera when speaking (not screen)
  • Dress professionally (at least top half)

In-Person (Coffee, Lunch)

Pros:

  • Strongest connection
  • Most memorable
  • Can extend beyond 30 minutes naturally

Cons:

  • Requires travel
  • Takes more time (theirs and yours)

Tips:

  • Arrive 10 minutes early
  • Offer to buy their coffee
  • Bring notebook and pen
  • Dress professionally (one step above casual)

Rule: Let them choose the format. Most prefer phone or video.

After the Interview: The Follow-Up

Immediate Follow-Up (Within 24 Hours)

Send a thank-you email:

Subject: Thank you for your time!

Hi [Name],

Thank you so much for taking the time to speak with me today. I really appreciated learning about your transition from [X] to [Y] and your advice on [specific thing they mentioned].

Your suggestion to [specific action—e.g., focus on SQL skills, reach out to X company] was especially helpful—I'm going to start on that this week.

If there's ever anything I can help you with, please don't hesitate to reach out.

Thanks again!

[Your Name]

Why it matters:

  • Shows professionalism
  • Reinforces relationship
  • Keeps you top of mind

Medium-Term Follow-Up (1-3 Months)

Send an update:

Subject: Quick update (and thank you again)

Hi [Name],

I wanted to give you a quick update since we spoke a few months ago.

I took your advice and [specific action you took based on their advice—e.g., completed a SQL course, applied to companies you recommended], and I'm happy to report that [outcome—e.g., I landed an interview at X company, I got certified].

Thank you again for your guidance—it made a real difference!

Hope things are going well on your end.

[Your Name]

Why it matters:

  • Shows you took their advice seriously
  • Keeps relationship warm
  • Positions you as action-oriented

Long-Term Follow-Up (6-12 Months)

Periodic check-ins:

Subject: Long time—hope you're doing well!

Hi [Name],

It's been a while since we spoke, but I wanted to reach out and say hello.

I'm happy to share that [major update—e.g., I transitioned into a sales role at X company, I completed my transition into product management]. A lot of that was thanks to your advice when we first spoke.

Hope things are going well with [something specific about them—their company, role, project]. Would love to catch up sometime if you're open to it!

[Your Name]

Why it matters:

  • Turns one-time conversation into ongoing relationship
  • You’re now in their network
  • Opens door for future opportunities

How to Turn Informational Interviews Into Job Offers

Step 1: Build Multiple Relationships (Not Just One)

Goal: 5-10 informational interviews over 2-3 months

Why: Odds of one person helping you land a job: 15-20%. Odds of 10 people: 80%+.

Step 2: Ask for Introductions

At the end of every interview:

“Is there anyone else you’d recommend I talk to?”

This compounds:

  • Person A introduces you to Person B
  • Person B introduces you to Person C (a hiring manager)
  • Person C has an opening

Real example:

  • Interview 1 → Learn about field
  • Interview 2 → Get introduction to Person 3
  • Interview 3 → Person 3 mentions “We’re hiring, want me to refer you?”
  • You get interview (skipping HR screening)

Step 3: Stay Top of Mind

When they post on LinkedIn: Comment with value

When you read relevant article: Share with them

When you achieve a milestone: Update them

After 3-6 months of this, they think of YOU when an opportunity arises.

Step 4: The Soft Ask (When Appropriate)

If conversation goes well:

“I’d love to be considered if any opportunities come up at [their company]. Would it be okay if I sent you my resume to keep on file?”

Most will say yes. Now you’re in their mental Rolodex.

Common Informational Interview Mistakes

Mistake 1: Asking for a Job Directly

Problem: “Can you get me a job?” kills goodwill

Fix: Ask for advice. Jobs follow naturally.

Mistake 2: Being Unprepared

Problem: Asking generic questions shows you didn’t research

Fix: Research their background. Prepare specific questions.

Mistake 3: Taking Too Much Time

Problem: Booking 60 minutes or going over your time

Fix: Ask for 20 minutes. End on time (even if they want to continue).

Mistake 4: Not Following Up

Problem: One conversation, then disappearing

Fix: Send thank-you. Update them in 1-3 months.

Mistake 5: Only Focusing on Yourself

Problem: Never asking how you can help them

Fix: Always ask “Is there anything I can do to help you?”

Your Informational Interview Action Plan

This Week:

  • Identify 5-10 people you want to talk to (LinkedIn, company websites)
  • Draft 3-5 outreach emails (use templates above)
  • Send first round of requests (aim for 3-5 this week)
  • Prepare 10-15 questions you want to ask

Next 2-4 Weeks:

  • Conduct 2-3 informational interviews
  • Send thank-you emails within 24 hours
  • Ask for introductions at end of each call
  • Take detailed notes (what you learned, action items)

Month 2-3:

  • Continue outreach (aim for 1-2 interviews per week)
  • Follow up with previous contacts (share updates)
  • Act on advice received (courses, applications, networking)
  • Build relationships (comment on LinkedIn, share articles)

Month 4-6:

  • Send updates to everyone you interviewed
  • Ask for introductions to hiring managers (if relevant)
  • Continue periodic check-ins
  • Turn informational interviews into ongoing relationships

Building your professional network? Check out these guides:

The Bottom Line

Informational interviews are one of the highest-ROI networking strategies.

Why they work:

  • 70-90% response rate (when done right)
  • You learn insider knowledge you can’t Google
  • You build relationships that lead to hidden job opportunities
  • People genuinely want to help

How to do them:

  1. Identify 5-10 people (prioritize warm connections first)
  2. Send personalized requests (use templates above)
  3. Prepare 10-15 thoughtful questions
  4. Conduct 20-30 minute conversation
  5. Send thank-you within 24 hours
  6. Follow up every 1-3 months with updates

The compound effect:

  • 1 informational interview = 1 relationship
  • 10 informational interviews = 10 relationships + 5-10 introductions
  • 20+ relationships = You’re now “in the network”
  • Result: Jobs find YOU (not the other way around)

Action plan:

  • Send your first 3 requests this week
  • Aim for 2-3 interviews in the next month
  • Build this into a habit (1-2 per month ongoing)

Don’t wait for the perfect time. The best time to start networking was 5 years ago. The second-best time is today.

Send that first email now.

The Dropout Millions Team

About the Author

We help college dropouts build real wealth without traditional credentials. Our guides are based on real strategies, data-driven insights, and the lived experience of people who left college and made it anyway. Financial independence isn't about having a degree—it's about having a plan.