Let me take you back to one of the most pivotal moments in my career. I was at a crossroads, unsure if I should keep going on the same path or pivot toward something new. I didn’t have a clear roadmap, but I did have one thing: curiosity.

That curiosity led me to have conversations with people I admired, respected, and was simply intrigued by. These weren’t job interviews. They were informal, curious, human-centered conversations. And those conversations completely shifted my career trajectory.

Welcome to the art of informational interviews—a deeply underrated tool in career transformation and discovery.

Why Informational Interviews Matter More Than Ever

The traditional job hunt is outdated. Instead of waiting for roles to open or applications to be reviewed, informational interviews allow you to create your own opportunities, build real relationships, and get insider insight into industries, roles, and cultures.

Beyond the tactical benefits, these interviews also help bridge the gap between the head and the heart.

From a Western psychology perspective, this aligns with the concept of experiential learning—we learn most effectively through action and human connection.

In Eastern philosophy, this is the equivalent of learning through direct transmission—wisdom passed from teacher to student, human to human.

“When the student is ready, the teacher will appear.” – Lao Tzu

In many ways, the person you speak with becomes a mirror—reflecting what’s possible and guiding your next move.

The Two Types of Informational Interviews

1. The Curious Explorer
This type is all about learning. You’re not trying to land a job here; you’re in exploration mode. You’re gathering stories, pathways, and lessons. This is perfect when your career vision is still a little fuzzy.

2. The Consultant Approach
This one is for when you have more clarity. You’re not just learning—you’re showing up with value. You're pitching ideas, listening for pain points, and positioning yourself as a solution. Many people (myself included!) have used this approach to open up job opportunities that never existed before.

Who to Talk To: Build Your Circle

The beautiful thing is—you already know people who know people.

Start here:

• Old coworkers, mentors, alumni

• Friends of friends (LinkedIn is your goldmine)

• Professors, coaches, and event speakers

• People you admire on social media

• Entrepreneurs, startup founders, investors

Also, don’t sleep on:

• Alumni networks (college, bootcamps, coaching programs)

• Industry-specific communities

• Nonprofits or community orgs

• Your current workplace (yes, start inside!)

Eastern perspective: Your network is your karmic field. Each relationship holds potential. Nourish it with care.

How to Structure a Powerful Informational Interview

Here’s a simple yet powerful format I’ve used countless times:

1. Set the container
   "Thanks for taking the time today. How much time do you have?"

2. Introduce yourself with clarity
   "I've worked in X for the last few years, and I’m now exploring ways to do more meaningful work in Y."

3. Share your why
   "I wanted to connect because your journey from [industry] to [industry] really inspired me."

4. Ask deep questions
   Think like a journalist, not a job seeker. Ask about their story, values, and lessons learned.

5. Share your relevant experience
   When the moment is right, share a story or example of your work.

6. Ask for feedback
   "Given what you know about the space, what gaps do you see in my experience—and how can I bridge them?"

7. Ask for other contacts
   "Is there anyone else you'd recommend I speak to?"

8. Close with presence
   "Thank you again. I'd love to keep in touch and share updates as I continue this journey."

Sample Questions to Guide Your Conversations

➡️ About Them

• What led you to this role or industry?

• What part of your day energizes you most?

• What keeps you up at night?

➡️ About the Role

• What are your biggest wins recently?

• What are the top 3 skills someone needs to succeed in this role?

• What parts of your job are most challenging?

➡️ About the Organization

• How would you describe the culture?

• What kind of people thrive here?

• What’s the feedback and growth process like?

➡️ About You

• Based on what I’ve shared, where could I make the biggest impact?

• What gaps do you see, and how could I start closing them?

• What would you do differently if you were in my shoes?

📝 Exercises to Move from Insight to Action

1. Brainstorm People to Interview:
   List people across your network or dream companies whom you’d love to learn from.

2. Clarify Your Purpose:
   For each person, are you:

• Exploring an industry?

• Exploring a role?

• Exploring a transition?

3. Commit to a Number:
   How many informational interviews will you conduct this month? Who will you contact first?

4. Reflect After Each One:
   Ask yourself: What did I learn? What surprised me? What next step am I inspired to take?

Closing Wisdom: Progress Over Perfection

Remember: you are not asking for a job. You are planting seeds. Some of these seeds will grow into friendships, mentors, collaborations, and yes—maybe even job opportunities.

But even if they don’t, each conversation gets you one step closer to clarity.

“When you walk with purpose, you collide with destiny.” – Bertice Berry

Let your curiosity lead. Let your presence speak. Let your story be heard.

And most importantly—follow up, keep in touch, and keep growing.

I’ll be cheering you on.

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Let me know if you’d like a sample script or a LinkedIn outreach message template to go along with this! 🌱