5 Questions to Ask During an Informational Interview

Author: Sean O’Keefe

What career is right for me?

Answering this question can be a confusing and exhausting process. Where do you begin and to whom do you go for advice?

Sometimes, you may think you’ve found the perfect job but wonder if the description online accurately describes what you’ll do in the role. Or you may be considering many different options at once and feeling unsure about which to pursue. What questions should you be asking to help you make an informed decision?

Setting up time to chat with someone working in the position or at the company you’re considering is a great way to get an inside perspective into what that career entails. These chats are often called informational interviews, or, as I like to call them, career conversations.

Career conversations are a means to informally learn about roles, organizations, and industries. They’re also a strategic way to develop internal advocates, provide you with knowledge needed to land positions you are seeking, and be referred into formal interview processes.

Land the Conversation

The first step to conducting a successful career conversation is to get a professional to say yes to your outreach request. Make a list of the organizations you want to work for, then research professionals at those companies who are about five to 10 years further into their careers and may be in a position to make entry-level hires.

Successful outreach messages are short and polite. Give a sentence of context about who you are, mention why this specific person could be helpful to you, and be flexible in scheduling. For example:

“Hi [name]. I’m a final-year student at [university] and I’m exploring my career options in organizational strategy. I am reaching out to you to request a short conversation so I can learn more about your role and how you got here. Your experience and advice would really help me make more informed choices as I start my career. I’m happy to speak at a time convenient to you.”

Most important, I suggest that you send a follow-up message about two days later, then another three days after that if you still don’t get a response. Persistence is key. If you still don’t hear from the person, look for your next best alternative.

Once you’ve set up time to chat, you need to prepare. Write down a set of questions in order of priority, then adjust as needed during the conversation. It’s OK to go off-script too; these questions are there to guide your conversation. Remember that you’re there to learn as much as you can and build a relationship, which are more important than getting through your prepared questions.

Set the Stage

Once you land the virtual or in-person meeting, kick things off with some small talk. Start with a few simple, open-ended questions before asking about their career. Your conversation should be driven by genuine human connection—it shouldn’t feel like an investigative interview.

Thank the other person for taking the time to chat with you. Then, in the first minute or two, you might ask how their day is going, where they are located (a great conversation starter for video calls), or what they are currently working on.

Next, give a short overview of who you are and why you are interested in speaking with them. Touch on the highlights of your education and your work and/or internships and be open about any current decisions or uncertainty you’re facing. This will give the other person context so that they get to know you a bit better and can be most helpful to you.

Get Your Answers

Now it’s time to get the answers you are looking for.

The five questions below are designed to help you get an inside view into the company or career you are interested in, as well as connect on a human level with the person you’re speaking with.

1. Could you walk me through your career path, starting with your experiences at [name of college they attended] and any internships or jobs you had before your role as [name of current position]?

This question will push the other person to share the most relevant details of their career path and how they ended up in their current job. It also shows that you did some research about their background and education. Asking this question gives you a view into the key decisions and stepping stones that propelled them to where they are today (and how you can get there, too).

Potential follow-up question: What did it take to move from one position to another?

2. I understand you [share what you know about their job duties]. Can you provide more details about what your typical day/week looks like?

If you’re interested in learning more about the daily rhythms and routines of this person’s work, this question can help to demystify their job responsibilities and tasks. As the person is answering, ask yourself whether you could imagine yourself waking up every day and happily doing the work they are describing. Would you find the best parts of the role inspiring? The toughest parts tolerable?

Potential follow-up question: What part of your job do you find the most interesting, as well as the most challenging?

3. Which skills are most important for a job like yours?

Understanding what skills are required for their job is key, actionable information. It gives you a roadmap of which capabilities you might need to learn or improve upon should you pursue a similar role. Keep in mind that this answer will likely vary depending on the role and tenure of the person. Employees at the bottom of the hierarchy are likely to use more technical and detail-oriented skills to get the job done, while more senior employees likely spend more time managing, developing, and leading others.

Potential follow-up question: Are there any additional skills that you think will be especially useful in the next five years for a student like me entering the field?

4. What do you think is the best way to earn an internship (or job) in this industry (or at this company)?

A professional who does (or has done) the job you are considering applying to will be able to give much more concrete and useful advice than any article you read. Companies’ websites are sometimes vague about what they look for in applicants, so asking a hiring manager or current employee is likely to yield more actionable insights. You might also learn about skills or experiences that you can invest in to raise your odds of getting hired in your desired field.

Potential follow-up question: Is not knowing [skill name] a deal-breaker?

5. I’m really interested in speaking with people [in X field/in Y role/at Z company]. Who else would you recommend that I connect with?

This question is valuable because it opens the possibility for you to engage in additional career conversations that can increase your social capital and broaden your opportunities to earn positions in the hidden job market (positions that are not advertised online). Based on your interests, you can ask about other employees at the same company, professionals in a specific field, or people with a similar set of life experiences who share some of your interests. This question should be asked toward the end of the conversation.

Potential follow-up question: Would you mind making an introduction to [person’s name]?

Don’t be afraid to stray from this list. You bring your personal experience and goals into the conversation, so ask questions that you are truly curious about relating to the other person’s career. You will likely be surprised and excited by how gracious and helpful people can be—even highly successful and busy professionals.