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Unlocking the True Potential of Informational Interviews

Informal interviews are not a waste of time if you use them right—here’s how.

Read time: 4 minutes

Hi Proactive Professional,

As the holiday season rolls in and many of us travel for Thanksgiving, it's a prime time to step back from the relentless pace of work for a well-deserved break. This period often invites reflection: Are you content in your current role? What are your aspirations going forward? How can you start moving towards your goals?

I found myself in a similar scenario earlier this year. Uncertain about my next career move, I reached out to past mentors and colleagues for guidance. I even discussed my aspirations with my executive team at Blade. Then, through a combination of cold outreach and warm introductions, I was speaking with people in increasingly interesting fields doing things that could never fit into the typical career path I had once envisioned for myself.

And I loved it! Well, except for the conversation around why the anime NFT market in Japan was the next big opportunity. Let's just say that conversation got cut a bit short…

This is the power of the "informational interview." These were pivotal in understanding the types of work that I could do outside of the career path I thought I may be boxed into. Depending on what your goals are, they can sometimes turn into a job opportunity.

Informational interviews helped me understand that my next move was not nearly as limited as I thought. I could chase something I'm passionate about and form a business around it. In fact, you're engaging with part of that business as you read this!

My fiancé even chocks her most meaningful career change up to an informational interview. 

A few years back, she had been working in publishing and was feeling unfulfilled, unhappy, and truthfully, broke. She reached out to a peer from college who had expanded beyond publishing herself to build her own brand development agency. My fiancé explained the way she was feeling, what she enjoyed about her work, and what she didn’t enjoy. The peer asked if she had ever considered freelancing so she could find out exactly what kind of writing she enjoyed. Eventually, this led to her discovery of copywriting, which is her current role.

These exchanges are more than mere chats; they are gateways to understanding and advancing in our professional lives. So today, let's dive into how we can harness the full potential of informational interviews to reflect effectively and learn how to achieve our ambitious goals.

Ways We Can Get the Most Out of Informational Interviews:

1. Making Every Question Count

First things first, you need to enter every informational interview with a mindset of curiosity and learning. Each question should serve a purpose, whether it's to gain industry insights or to understand the interviewee's career trajectory.

Go Beyond LinkedIn: When preparing questions, dig deeper than what's visible on a LinkedIn profile. Show that you've done your homework, but you're also interested in the story behind the profile information. "I see you switched industries but kept a similar role, what were some of the unexpected challenges and benefits when navigating that?" This approach shows respect for their experience and an eagerness to learn from their unique path and expertise.

Seek Wisdom, Not Just Facts: Facts can be Googled. Wisdom requires generative AI…kidding. Although AI can seem wise, there is no replacing unique pearls of wisdom from a single person's experience. Use your time to extract this wisdom. Questions like, "What do you wish you knew when you were in my shoes?" can open a treasure trove of insights and advice that you can't find in any article, job posting, or next-gen AI chatbot.

2. Offering Value in Return

An informational interview shouldn't be a one-way street. Consider what you can offer. Maybe it's a fresh perspective on a new market trend or a connection to someone in your network that could benefit them. They are giving you their time, their most valuable resource, with no expectation of anything in return. If there is any way you can add value to them, it's important you go out of your way to do so.

The Two-Way Street: If appropriate, engage in a genuine exchange of ideas. If you come across an article or a case study relevant to their work, share it. Beyond that, never leave an informational interview without asking if there is anything you can do to be helpful to them. It shows you're not just there to take but also to give.

Follow Through: If during the interview, you find an opportunity to assist or provide a resource, make a note and follow through. A quick message with a link to a resource or an introduction email can go a long way in establishing a meaningful connection.

3. The Art of Listening

Listening is perhaps the most crucial skill in any informational interview. It's not just about waiting for your turn to speak—it's about truly hearing and understanding the other person's perspective.

Active Engagement: Nodding along as they speak, asking follow-up questions, and summarizing their points to ensure you've understood them correctly are all signs of an active listener. This not only helps you grasp their insights better but also shows the interviewee they have your full attention.

The Power of the Pause: Don't be afraid of silence. Pausing after they've finished their point before you ask another question can give them space to add more depth to their answers.

4. The Follow-Up: Not an Afterthought

The interview may be over, but the relationship-building is just beginning. Your follow-up can be the differentiator between a forgotten conversation and a lasting connection.

The Gratitude Gesture: A thank you note is non-negotiable. Make it personal and mention specific points from the conversation that you found valuable. It's the absolute least you can do.

Keep the Door Open: If fitting, express your desire to keep in touch and ask for the best way to do so. Whether it's connecting on LinkedIn, a quarterly catch-up call, or an offer to assist them with a project, make it clear that the conversation was just the beginning.

BONUS: 5. 25 Questions for Informational Interviews

Informational interviews have the potential to add immense value to our professional lives, not just for the insights we gain but for the relationships we build and nurture.

Next time you schedule one, go in with the intention of creating a two-way flow of value. It could lead to doors you never knew existed.

What I’m committing to this week for building relationships (time commitment ~6 hours):
  • 🤝 Connecting with CEO's and founders at a tech event (~2 hours)

  • 🦃 Feasting with 30 family members at my childhood home during my favorite holiday: Thanksgiving (~3 hours)

  • 🗣 Speaking about networking in one of my former professor's business classes at Carnegie Mellon (~1 hour)

  • 🤔 Reflecting on my week this Friday: What questions have worked best to get people talking during my informational interviews? (~15 minutes)

What are you committing to this week? Reply to this email!

Best of luck building,

Devin