Informational Interviews: Networking Made Easy

How to find thought leaders for informational interviews and what questions to ask them that will help your job search

The most valuable opportunities often remain hidden from job boards and company websites. Senior roles that are offered only to those already deemed qualified and connected.

Enter the informational interview—a powerful tool that can unlock doors to your career pivot. Mastering this skill can help you land your dream job.

Informational interviews are your most powerful networking approach. They provide insights no job description can offer while creating relationships that can sustain your career for years to come.

Table of Contents

Informational interview conversations aren't just nice-to-have—they're essential components of a successful long-term career strategy. Learn why with these topics:

• Why Informational Interviews Matter

• Step 1: Approach Your Interview Targets

• Step 2: Prepare Before the Interview

• Step 3: Make the Most of Your Interview

• Step 4: Build Lasting Relationships

• Key Informational Interview Takeaways

Why Informational Interviews Matter

There are three reasons why you should be information interviewing your ass off.

1. Informational Interviews Inform Your Search

Informational interviews are essential to helping you find out more about the type of industry, company, or role you're interested in. They offer a unique opportunity to test your assumptions about a position directly with someone who has a role that you’re interested in doing next.

2. Informational Interviews Alert Peers to Your Desires

These conversations create visibility in the hidden job market - roles that are open but not advertised. This exposure can put you on a shortlist even before the position is advertised or alert a potential hiring manager that they should be thinking about hiring someone - you - for a role on their team.

3. Informational Interviews Expand Your Network

You should always ask your interviewee for three other people you should speak with. People like to feel connected, so asking this question lets them brag. It also helps you learn who else you should be interviewing.

Finally, their recommendations create a social obligation for that next connection to speak with you - more on this later.

Step 1: Approach Your Interview Targets

In Step 3: Choose a Role, Industry, and Companies, of the 7-step process, you’ve identified your dream role with several key companies in your target industry, and those that work in positions that interest you.

Generative AI can help you with that step, especially tools like Perplexity and LinkedIn, where you can identify the specific people you want to speak with.

Now it is time to do Step 4: Build Your Professional Network. Here you need to informational interview those key people you just identified.

• How to ask them to speak with you?

• How to ensure they respond, and with a yes?

You need to create a social obligation. A requirement they meet with you based on their relationship with their friend - not you. Best is a message to them that is something like this:

• Dear Susan. I was speaking with David recently and he said you are an expert on [x]. He said I should speak with you about [x], and your insight would help me. I am looking to enter the [x] field after many years in [y].

Do you see what I did there? I created a social obligation between Susan and David, for Susan to speak with me.

Yes, it is key that you have some connection with Susan. That’s also the power of LinkedIn or your emails. You can connect to anyone that matters within 2 degrees right now.

We are all connected to Kevin Bacon in 6 degrees or less. I’m connected in three.

• How many degress till you connect with Kevin Bacon?

At the same time, you’ll probably have a 65% success rate, even when you have a social obligation. Some folks just do not prioritize informational interviews. Such is life.

Step 2: Prepare Before the Interview

Before your informational interviews, be sure to do the following due diligence:

• Research industry terminology and jargon

• Identify key players and companies

• Understand current industry trends and challenges

• Prepare thoughtful questions

You will come across as a more serious candidate if you are familiar with the jargon and vocabulary. You can even use ChatGPT to figure out good questions to ask.

For example, you can ask ChatGPT a prompt like this:

• I am having an informational interview with a leader in [x]. What are 10 interesting and unique questions I can ask them that are not cliches or common Google searches?

This preparation establishes your credibility from the start of the conversation.

Don't limit your preparation to research. Work on your listening and conversation skills by practicing with ChatGPT’s voice mode. Focus on asking insightful questions and projecting positive energy—these social skills will be crucial during the actual interview.

Step 3: Make the Most of Your Interview

One of the biggest mistakes people make is turning informational interviews into one-sided conversations about themselves. Limit your personal introduction to a very quick overview that is focused on them.

• “Thanks for your time. I am interested in learning about your work with [x], since I have a background in [y] that I feel is relevant.”

Now acknowledge your connection. This establishes rapport and context for the conversation. Also mention early on that you're speaking with multiple industry experts. This foreshadows that you'll be asking for additional referrals later.

Ask Questions Like a Journalist

Approach the conversation with a journalist's curiosity and structure. Consider using a question framework like this:

1. How did you get into this line of work?

2. What aspects of your job do you enjoy most?

3. What's challenging or less enjoyable about your role?

4. How is this industry or role evolving right now?

5. What types of people tend to thrive in this field?

What other questions should we ask? What questions do you ask?

Seek the Full Picture

Don't shy away from asking about the downsides. Questions like "What's the most difficult part of your job?" or "What do you wish someone had told you before entering this field?" reveal crucial insights that job descriptions never mention.

Even sensitive topics like compensation can be approached tactfully: "From my research, it seems the typical salary range is [X]. Would you say that's accurate?" This framing asks for confirmation rather than personal disclosure.

Request Advice on Your Fit

Once you've established rapport, ask for an honest assessment:

• "I have a background in [y], can that be a basis for working in [x]? Where are potential gaps? How might I position myself more effectively in this field?"

Remember that one person's opinion isn't definitive—if you receive discouraging feedback, seek additional perspectives before changing course.

Ask for 3 More Contacts

Always be sure to ask for more contacts that you can speak with. This will expand your network and will let them brag about who they know - a win for everyone! Be sure to get their contact details, not just their name.

Now you have more people to send an informational interview request with, expanding your network of contacts and potential job opportunity referrals.

Step 4: Build Lasting Relationships

Send a prompt thank-you email to express gratitude after the information interview. You can also consider sending a handwritten note to stand out. In 2025, a personal letter - handwritten! - will certainly get their attention.

Your message should specifically mention how the conversation helped you and, ideally, reference any concrete steps you've taken based on their advice.

Nurture the Relationship

The true value of informational interviews emerges over time. Stay in touch by:

• Sharing relevant articles or resources that might interest them

• Inviting them to industry events or webinars

• Updating them on how you've implemented their advice

• Finding small ways to be helpful to them

You want to be seen as giving, not constantly taking. These ongoing interactions transform a single conversation into a meaningful professional relationship.

Be Judicious in Your Asks

The fastest way to burn a new connection is to immediately ask for favors or referrals. Only contact them when you have information to share that is relevant to them - an act of giving.

If a relevant position opens up weeks later, it's appropriate to mention you're applying and ask for advice on highlighting specific experiences in your application—but don't directly ask them to put in a good word for you. Let them offer that support themselves.

Key Takeaways

Do:

• Research thoroughly to demonstrate your commitment and credibility

• Prepare a concise personal introduction

• Send a thoughtful thank-you note that references specific insights gained

• Build genuine long-term connections

Don't:

• Ask basic questions that could be answered through simple research

• Dominate the conversation with your own story

• Make immediate requests for favors or referrals

• Let one negative interview discourage you from pursuing a path