Here at Happy Spectacular, we are really big fans of the informational interview. We believe that no one has a successful career alone, and the more people you connect with in your career, the better. As often as possible, we do our best to act as the facilitators for informational interviews for our clients, acting as the middle man when one of our clients says, “I’m interested in getting into [insert industry/company/job here], but I don’t know anyone in the field or close to it.” And we get to say (like the networking fairies we love to be), “We know someone in that area. Let me check with them and see if they would be cool with me sharing their contact info with you.”
When we talk about informational interviews, we are talking about two kinds:

  • True information gathering
  • Information gathering with the hope that this will lead to a job opportunity at the person’s company

Both kinds of meetings are valuable, valid, and helpful, but it’s important for you to be clear what your purpose is going into the meeting. We also think that it’s important to be clear and up-front about the meeting you’re requesting. If you ask for an information-gathering meeting, but really are angling for a job at their company the whole time you’re meeting with them, that can leave an odd impression. (At worst, turn the person off from hiring you or connecting you with others.)
In the, “I just want to soak up your information” meeting, your intention is to learn about the person’s role, company, industry, career path, career change, etc. A fact-finding mission at its finest. You should be prepared to take notes. At this point, you might not be able to really articulate how you want to use this information in your career, but be prepared to answer what about this person and their experience is of interest to you and to tell them a bit about your career so far.
The “I hope this connection somehow leads to an opportunity” meeting is less about amorphous learning and more about active connection and opportunity. It’s even more important in this meeting that you have done the research on your counterpart, and you should treat this a little more formally. Be prepared with your personal elevator pitch and be able to talk about why you want what you want, and how you hope they can help you. There is a fine balance between being straightforward about what you are looking for and coming across as a user. Networking is reciprocal!! Make sure you’re also getting to know the person you are talking to, and actively thinking about what you might be able to do for them.
Once you figure out what your goal is, the hardest part for many can be sending that cold email. The best option to start with is obviously someone you already know, even if you have a tenuous connection at best. Reach out to that person from high school who is now working at your dream company, or the former colleague who changed fields, or the neighbor that you always see walking your dog and you chatted up at last year’s block party.
You can also ask for an intro of a friend of a friend. Tell the people in your network what you’re looking for, and often someone will say, “Oh, I know someone like that!”  Ask if they can send an email introduction so you can connect with your potential interviewee. The other option is taking the initiative to find someone on your own, using LinkedIn as a way to message someone. As one of our coaches, Jodi Wellman, says, “Read a great story in the news about a company that intrigues you? Look them up online and reach out to someone on their About Us or Team page who is in a role similar to the one you want to research. Meet someone interesting at a networking event and want to learn more? Tell them that, and make a date for a conversation to chat.”

Now for the good stuff: tips, flow, and questions for your meeting.

  • Do your homework! Research the person and company in advance. Don’t ask questions that make it look like you didn’t bother looking them up on LinkedIn, or like you never Googled the company. (So, don’t ask the person who has been gracious enough to meet with you how long they’ve been at the company. Ouch.)
  • Pick up the check. If you ask someone out for coffee, you should generally buy for them. To avoid the awkward check-out tango, either ask for their order in advance or get there early to buy a gift card they can use to pay for their drink, so you don’t have to give up your seat to take care of the payment.
  • Meet in person. At least try to meet in person, but be aware of their schedule too. If it seems like it’s becoming difficult to find a time, offer to do a video call.
  • Thank the person before the meeting begins! “I know your time is valuable, and I’m so appreciative you’re willing to take this 30 minutes to chat with me.”
  • Have questions prepared, either printed out or written down.
  • Take notes! It makes you look prepared, and you’ll get more out of the meeting. The person will likely expect it, so don’t worry about looking strange.
  • Extend your network. At the end of your conversation, if the conversation has been productive and you want to continue learning about this area, ask who your interviewee thinks you should talk to next, to continue your exploration.
  • Follow up. Send a follow-up note to your interviewee within a day to thank them again (this will go a long way), and let them know you’d like to stay in touch. This way you can stay top of mind if a role or introduction opportunity comes along.
  • Sit with it. Whether you want to take notes immediately after your meeting or just take the time to check in with yourself, figure out how the meeting made you feel. Excited? Energized and engaged? Daunted? Heavy? Anxious? This is part of the work to help you figure out if the role/ company/ industry really is the right path for you to pursue further.
  • Pay it forward. Always be willing to make time in the future for someone who might want to talk to you for an informational interview. What goes around always comes around!

These are some common questions for informational interviews to help get you started; choose questions and come up with your own based on what your goals are for the interview.

  • What inspired you to get into your field in the first place?
  • I read about your previous jobs on LinkedIn, but can you elaborate a bit more on your career path and how those roles came to be?
  • What’s a typical day or week like for you?
  • What are the high points of your role? What about the low points?
  • Where do you see the future of this role going?
  • What surprised you about your role? What about your industry?
  • What’s next for you in your career?
  • What advice do you have for someone like me, looking to get into the field?
  • How do people break into this (role/company/industry) with very little experience?
  • How would you describe the culture at your organization? Is that typical for the industry?
  • What kinds of people are successful at your company?

Many of our clients, and most people we come across, think it’s an imposition to ask people to spend time in an informational interview. In our experience, a vast majority are happy to share what they’ve learned and help out a career transitioner. After all, people love to talk about themselves. Give the person you’re interviewing a chance to share their experiences and ideas (remembering that this meeting isn’t about you at all), and they’ll leave feeling like it was time well spent. Especially if you let them know how much you appreciate their valuable words of wisdom.

Nora Philbin

Nora is a co-founder of Happy Spectacular, which she still can't really believe, and she's on a lifelong quest for the world's best cheeseburger (applicants accepted).