Conducting a Successful Informational Interview and 20 Questions to Ask

By Shawn Lipton


Bill Burnett and Dave Evans, authors of “Designing Your Life (a book I highly recommend), describe an informational interview in similar terms as if your lost and asking for directions. If you don’t know where you’re going (and your phone has died), would you hesitate in asking someone how to get to your destination? Most of you would not. If you are hesitant to conduct informational interviews or feel uncomfortable, simply look at it as if you’re asking for directions, but in this case it’s all about your career destination.

Informational interviews are not about job searching, but instead should be focused on learning as much as you can about a particular career path, industry, or specific company. It’s all about gaining insight and connecting with a community.

You should NEVER ask for a job in an informational interview.

You can show your enthusiasm and ask after learning more about a company, how one may go about working there or how does one go about getting a job at ABC company, but never look at informational interviews as transactions – they’re all about relationships.

Some experts say 60-80% of all jobs do not get posted!

The absolute best way to learn about these jobs is through connecting with professionals and building relationships. It’s an opportunity to create an advocate so when a job is available you will have a great potential contact.

Informational interviews are all about getting advice, learning about an area of interest, and connecting in a one-on-one setting with a professional who can guide you in your career development.

To reiterate, you need to enter into every single one of these encounters with a singular goal: to learn and connect. Occasionally, however, a job will materialize from an informational interview. I have worked with thousands of students and professionals who have gone on 10, 20, 50, even up to 100 informational interviews and have gotten to the point that they were sick of them and found them useless.

When they thought they could not possibly do one more, a job opportunity arose. Now that you are clued in on the why, let’s focus on the how.

How to effectively conduct an informational interview

Be prepared, be genuine, be a good listener, have good questions, and engage in the conversation.

Preparation focuses on two aspects:

1. Do your due diligence. Know who the person is, what they generally do, and a good bit about the company he/she works for. Come across as genuinely interested and engaged. Preparation is the best way to do that.

2. The second component of preparation is to remember that the conversation will always turn back to you, and when it does you want to be prepared with your story. In most cases, you will be answering the question, “Why are you interested in this field?” or the prompt, “Give me a sense of your background.” There are many variations of this, but you will generally respond with the same concept – which in a very conversational way shows your passion or interest in a specific field, a brief background of your experience, and most importantly, your personal story is always tailored to your audience. This last part will change depending on who you’re talking to and what company they work for.

It’s a natural way to talk a bit about your background.

Your story is not something you regurgitate or something that is canned. You need to tailor it to your audience and it needs to be completely conversational in tone; introduce yourself in a professional manner, but as if you were having a conversation with a friend.

The following three tips will help in the process of creating your story.

1. Know your audience. You cannot create common ground or relate to someone if you have no knowledge of their background. Think about your personal and professional interests and how certain experiences may particularly resonate with your audience.

2. Prepare and practice. Once you know your audience, start preparing for the meeting by thinking about how you may be able to connect to this individual. Think about all the possible experiences or knowledge you may be able to share.

Practice out-loud, putting your experiences into story format (see a good example below).

Always, always, always practice out loud. Getting used to saying the words and practicing out-loud helps you be more conversational. Sometimes recording yourself can also help. If you are getting bored or confused listening to yourself, you know you need to re-work. Never memorize, INTERNALIZE!

3. Be yourself.

Here’s a good example for a recent graduate, but can be followed by anyone early in career:

Well, my dream job is to be a buyer, similar to you, for Nordstrom’s, but I realize that’s some ways off for me. I have worked in retail since I was sixteen, and, besides being a top sales performer, I’ve developed a keen eye on fashion trends and what types of styles are attractive to the consumer. So, at this point, I am looking for anything that will get me closer to my goal, whether that’s as a buyer’s assistant or maybe working on displays – a step in the direction that will give me additional knowledge and pertinent experience. I would, of course, love to hear your suggestions on how that may be done or a path you think would be ideal for me.”

Keep your story succinct, nothing more than 45 seconds.

The 20 Best Informational Interview Questions

To conduct a successful informational interview, always preface questions with knowledge. It takes a seemingly generic question and makes it relevant or much more interesting. For example, “I was reading your LinkedIn profile and noticed… (then ask the question).

The questions below are in no particular order, and you should make sure in the interview that you’re not just going through a list of questions one-by-one. It’s not an inquisition, but rather a way to start a conversation.

Use these questions as a guide and pick six or seven that may be most on point for your interview.

Weave the questions into the normal conversation and use them to continue a conversation.

Never just look at an informational interview as a repetitive process of question-answer.

These questions are the starting point. When you combine them with knowledge obtained from the conversation, as well as your research, you will be able to create a compelling question that leads to more fruitful dialog.

1. In looking on LinkedIn, you’ve really had an amazing run, what are some of the things you’ve really done right?

2. Anything you wish you would’ve done differently?

3. I see you just made a move to ABC, what made you leave DEF. (Or – You’ve been there a while, what has kept you so engaged?)

4. For someone trying to break into the field but is having trouble getting started, what do you recommend I could do to differentiate myself?

5. I heard the culture of ABC really focuses on … (keep it positive), would you agree or what has been your experience.

6. What about your position makes you jump out of bed in the morning? Is there anything that makes you want to roll over and hit the snooze button?

7. For someone with very limited experience in the field, what one piece of advice would you give me that could help me break into the industry?

8. If you had to start your career again, would you choose the same path? Why or why not?

9. What are the main reasons that people do not succeed in this field?

10. Would you mind sharing with me one of the more challenging problems you’ve been working on?

11. Can you share some of the more challenging situations you’ve had to face in your position?

12. If you were looking at a resume from a candidate with decent experience but not completely on point for the role, what types of things would make you take a second look and say, “Hmm, I’d like to learn more about this person.”?

13. If you could have an informational interview with anyone in the field, who would it be and why?

14. What types of professional development do you think you need to stay relevant?

15. What skills and personal characteristics do you think are needed to thrive in this field?

16. Was this the profession you always thought you would pursue? When did you make the decision or did you just fall in to it?

17. What is the greatest compliment you have ever received regarding your work?

18. What has been your primary motivation to achieve success in your career?

19. I’m just trying to get a lay of the land and learn as much as I can; do you know anyone else I can talk to?

20. Thank you so much for your time and for giving me such a great sense of the company, it’s made me even more excited to pursue opportunities at ABC. How does one go about getting a job here?

Shawn Lipton

Shawn Lipton
The Trusted Coach

I have been a coach for 15 years, first working at Seattle University and the last almost seven years running my own career and corporate coaching practice. There is nothing I love more than helping people identify what may be a fulfilling career and then teaching them how to develop their story to land an ideal role.

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